United States v. Santana
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Opinion
USCA1 Opinion
UNITED STATES COURT OF APPEALS
FOR THE FIRST CIRCUIT
_________________________
No. 93-1393
UNITED STATES OF AMERICA,
Appellant,
v.
RAFAEL SANTANA AND FRANCIS FUENTES,
Defendants, Appellees.
_________________________
APPEAL FROM THE UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF MASSACHUSETTS
[Hon. Frank H. Freedman, Senior U.S. District Judge]
__________________________
_________________________
Before
Selya, Cyr and Boudin, Circuit Judges.
______________
_________________________
Kevin O'Regan, Assistant United States Attorney, with whom
_____________
A. John Pappalardo, United States Attorney, and Andrew Levchuk,
___________________ ______________
Assistant United States Attorney, were on brief, for appellant.
Leonard H. Cohen, with whom William A. Rota, Nancy A. Lyon,
_________________ _______________ _____________
and Cain, Hibbard, Myers & Cook were on brief, for appellee
_____________________________
Santana.
Peter L. Ettenberg, with whom Gould & Ettenberg, P.C. was on
__________________ _______________________
brief, for appellee Fuentes.
Wendy Sibbison, Burton Shostak, and Moline, Ottsen, Mauze,
_______________ ______________ ______________________
Leggat & Shostak on consolidated brief for Massachusetts Ass'n of
________________
Criminal Defense Lawyers and National Ass'n of Criminal Defense
Lawyers, amici curiae.
_________________________
September 16, 1993
_________________________
SELYA, Circuit Judge. In the six decades since Justice
SELYA, Circuit Judge.
_____________
Roberts noted that "[s]ociety is at war with the criminal
classes," Sorrells v. United States, 287 U.S. 435, 453 (1932)
________ _____________
(Roberts, J., dissenting), hostilities have escalated and
armaments have grown more destructive. Here, the government's
weapon was 13.3 grams of heroin, 92% pure, delivered into the
stream of commerce as part of an effort to gain the confidence of
suspected drug traffickers. The district judge decided that the
government's guerilla tactics impermissibly endangered civilians
and dismissed the ensuing charge. See United States v. Santana,
___ _____________ _______
808 F. Supp. 77 (D. Mass. 1992). The United States appeals.
Although law enforcement officers might well profit from reading
the lower court's thoughtful opinion, we conclude that the court
exceeded its authority. Consequently, we reverse.
I. BACKGROUND
I. BACKGROUND
In 1991, the federal Drug Enforcement Administration
(DEA) mounted an elaborate reverse sting designed to bring a
mammoth heroin distribution network to ground. The DEA believed
that defendant-appellee Rafael Santana ran the ring from prison
through various henchmen, including defendant-appellee Francis
Fuentes. In the course of the sting, Fuentes asked an undercover
agent, posing as a heroin supplier, to furnish a sample of his
wares. The agent received a special dispensation from DEA
hierarchs and delivered 13.3 grams of heroin, 92% pure, to
2
Fuentes in August of 1991.1 The authorities never recovered the
sample.
There is a factual dispute over the size of the stakes.
The government, based on its agent's testimony, claims that the
deal under negotiation contemplated delivery of 141 kilograms of
heroin. It further claims, based on an informer's account, that
Santana's organization was capable of distributing up to 200
kilograms of heroin monthly. Appellees suggest that the
negotiations concerned a considerably smaller quantity of
narcotics, and that the organization, if it existed at all, was
far less ambitious. We need not enter this thicket; for present
purposes, the relevant finding is the reasonableness, at the time
the sample was furnished, of the government's belief that the
alleged organization had the capacity to manage widespread
distribution of heroin. It is not seriously disputed that the
government thought this to be the case; and, moreover, the
government's belief, given both the information in its files and
Santana's history he had been convicted in 1990 of conspiracy
to smuggle 1,000 kilograms of heroin was objectively
reasonable.
Having been made privy to the evidence collected in the
course of the government's indagation, a federal grand jury
____________________
1The heroin sample comprises about 2,500 doses of the size
and purity typically sold on the street. See Gerald F. Uelman &
___
Victor G. Haddox, Drug Abuse and the Law Sourcebook, 2.4(a) at
__________________________________
2-19 (1991). The DEA authorized delivery pursuant to section
III-E of the DEA's Domestic Operations Guidelines, 20 Crim. L.
Rep. (BNA) 3055-58 (Feb. 2, 1977).
3
returned a three-count indictment against seven defendants,
including appellees, in October of 1991. The defendants filed
pretrial motions seeking to dismiss the indictment on the ground
that the government acted outrageously in fronting so much heroin
and then losing track of it. A magistrate judge recommended that
the motions be denied. The district court rejected the
recommendation. Presuming that most of the unretrieved sample
reached end users, see id. at 79, the court found that the
___ ___
government's actions exceeded the bounds of propriety, see id. at
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USCA1 Opinion
UNITED STATES COURT OF APPEALS
FOR THE FIRST CIRCUIT
_________________________
No. 93-1393
UNITED STATES OF AMERICA,
Appellant,
v.
RAFAEL SANTANA AND FRANCIS FUENTES,
Defendants, Appellees.
_________________________
APPEAL FROM THE UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF MASSACHUSETTS
[Hon. Frank H. Freedman, Senior U.S. District Judge]
__________________________
_________________________
Before
Selya, Cyr and Boudin, Circuit Judges.
______________
_________________________
Kevin O'Regan, Assistant United States Attorney, with whom
_____________
A. John Pappalardo, United States Attorney, and Andrew Levchuk,
___________________ ______________
Assistant United States Attorney, were on brief, for appellant.
Leonard H. Cohen, with whom William A. Rota, Nancy A. Lyon,
_________________ _______________ _____________
and Cain, Hibbard, Myers & Cook were on brief, for appellee
_____________________________
Santana.
Peter L. Ettenberg, with whom Gould & Ettenberg, P.C. was on
__________________ _______________________
brief, for appellee Fuentes.
Wendy Sibbison, Burton Shostak, and Moline, Ottsen, Mauze,
_______________ ______________ ______________________
Leggat & Shostak on consolidated brief for Massachusetts Ass'n of
________________
Criminal Defense Lawyers and National Ass'n of Criminal Defense
Lawyers, amici curiae.
_________________________
September 16, 1993
_________________________
SELYA, Circuit Judge. In the six decades since Justice
SELYA, Circuit Judge.
_____________
Roberts noted that "[s]ociety is at war with the criminal
classes," Sorrells v. United States, 287 U.S. 435, 453 (1932)
________ _____________
(Roberts, J., dissenting), hostilities have escalated and
armaments have grown more destructive. Here, the government's
weapon was 13.3 grams of heroin, 92% pure, delivered into the
stream of commerce as part of an effort to gain the confidence of
suspected drug traffickers. The district judge decided that the
government's guerilla tactics impermissibly endangered civilians
and dismissed the ensuing charge. See United States v. Santana,
___ _____________ _______
808 F. Supp. 77 (D. Mass. 1992). The United States appeals.
Although law enforcement officers might well profit from reading
the lower court's thoughtful opinion, we conclude that the court
exceeded its authority. Consequently, we reverse.
I. BACKGROUND
I. BACKGROUND
In 1991, the federal Drug Enforcement Administration
(DEA) mounted an elaborate reverse sting designed to bring a
mammoth heroin distribution network to ground. The DEA believed
that defendant-appellee Rafael Santana ran the ring from prison
through various henchmen, including defendant-appellee Francis
Fuentes. In the course of the sting, Fuentes asked an undercover
agent, posing as a heroin supplier, to furnish a sample of his
wares. The agent received a special dispensation from DEA
hierarchs and delivered 13.3 grams of heroin, 92% pure, to
2
Fuentes in August of 1991.1 The authorities never recovered the
sample.
There is a factual dispute over the size of the stakes.
The government, based on its agent's testimony, claims that the
deal under negotiation contemplated delivery of 141 kilograms of
heroin. It further claims, based on an informer's account, that
Santana's organization was capable of distributing up to 200
kilograms of heroin monthly. Appellees suggest that the
negotiations concerned a considerably smaller quantity of
narcotics, and that the organization, if it existed at all, was
far less ambitious. We need not enter this thicket; for present
purposes, the relevant finding is the reasonableness, at the time
the sample was furnished, of the government's belief that the
alleged organization had the capacity to manage widespread
distribution of heroin. It is not seriously disputed that the
government thought this to be the case; and, moreover, the
government's belief, given both the information in its files and
Santana's history he had been convicted in 1990 of conspiracy
to smuggle 1,000 kilograms of heroin was objectively
reasonable.
Having been made privy to the evidence collected in the
course of the government's indagation, a federal grand jury
____________________
1The heroin sample comprises about 2,500 doses of the size
and purity typically sold on the street. See Gerald F. Uelman &
___
Victor G. Haddox, Drug Abuse and the Law Sourcebook, 2.4(a) at
__________________________________
2-19 (1991). The DEA authorized delivery pursuant to section
III-E of the DEA's Domestic Operations Guidelines, 20 Crim. L.
Rep. (BNA) 3055-58 (Feb. 2, 1977).
3
returned a three-count indictment against seven defendants,
including appellees, in October of 1991. The defendants filed
pretrial motions seeking to dismiss the indictment on the ground
that the government acted outrageously in fronting so much heroin
and then losing track of it. A magistrate judge recommended that
the motions be denied. The district court rejected the
recommendation. Presuming that most of the unretrieved sample
reached end users, see id. at 79, the court found that the
___ ___
government's actions exceeded the bounds of propriety, see id. at
___ ___
81-84. It thereupon dismissed count 3 of the indictment (the
count for which the 13.3-gram sample formed the corpus
______
delicti).2 See id. at 85-86. The court derived its authority
_______ ___ ___
from the due process clause of the Fifth Amendment, and,
alternatively, from its supervisory power. See id. at 86. The
___ ___
government moved unsuccessfully for reconsideration3 and now
appeals. We have jurisdiction under 18 U.S.C. 3731 (1988).
There are two main legal points in contention. First,
____________________
2Count 3 named only Santana and Fuentes. Hence, they are
the lone appellees.
3The briefs highlight several other factual disputes. By
and large, these disputes hinge on the admissibility of an
affidavit appended to the motion to reconsider an affidavit
which tries to shed light on the sample's ultimate disposition
and the agent's motive in delivering it. Because this affidavit
was not proffered originally, and because the lower court made no
findings concerning it, we consider only two undisputed portions
of the affidavit, namely, that the agent, in asking his superiors
to arrange for a sample, believed that "Fuentes was testing
whether I was a real drug dealer," and that supplying the sample
"was an important part of Fuentes' evaluation whether to go
forward with the deal." We will assume, as appellees implore,
that most, if not all, of the 13.3 grams of heroin reached end
users.
4
the government denies that its conduct was outrageous. Second,
the government asseverates that the district court lacked
authority under either the due process clause or the rubric of
supervisory power to redress injuries to third parties by
_____ _______
dismissing charges against appellees. On the facts of this case,
we think that both points are well taken.
II. THE DOCTRINE OF OUTRAGEOUS MISCONDUCT
II. THE DOCTRINE OF OUTRAGEOUS MISCONDUCT
Outrageous misconduct is the deathbed child of
objective entrapment, a doctrine long since discarded in the
federal courts. See, e.g., Sherman v. United States, 356 U.S.
___ ____ _______ ______________
369, 372 (1958) (rejecting an objective entrapment approach in
favor of a subjective approach). The doctrine's midwife was
Chief Justice Rehnquist (then Justice Rehnquist), who, in the
course of championing a subjective theory of entrapment,
speculated that the Court might "some day be presented with a
situation in which the conduct of law enforcement agents is so
outrageous that due process principles would absolutely bar the
government from invoking judicial processes to obtain a
conviction. . . ." United States v. Russell, 411 U.S. 423, 431-
_____________ _______
32 (1972). Seizing upon this dictum, the defendant in Hampton v.
_______
United States, 425 U.S. 484 (1975), attempted to construct an
_____________
outrageous misconduct defense rooted in the due process clause.
Hampton lost his case but succeeded in legitimating the doctrine,
albeit precariously.4
____________________
4In Hampton, a concurrence combined with the plurality to
_______
reject the appeal. However, the two concurring Justices switched
sides to form a different majority vivifying the doctrine of
5
Although it has a comfortably familiar ring,
"outrageous misconduct" is surpassingly difficult to translate
into a closely defined set of behavioral norms. The broadest
hints as to the content of the outrageousness standard lie in the
dictum that spawned the doctrine. Inasmuch as Rochin v.
______
California, 342 U.S. 165 (1952), is the case irrefragably linked
__________
with the legal rubric of fundamental fairness, one hint is found
in Justice Rehnquist's citation to Rochin. See Russell, 411 U.S.
______ ___ _______
at 431-32. A second hint is contained in Russell's explicit
_______
equation of outrageous misconduct with violations of "that
'fundamental fairness, shocking to the universal sense of
justice,' mandated by the Due Process Clause of the Fifth
Amendment." Russell, 423 U.S. at 432 (quoting Kinsella v. United
_______ ________ ______
States ex rel. Singleton, 361 U.S. 234, 246 (1960)). Picking up
________________________
on these clues, most courts apply a variant on the fundamental
fairness standard as a sounding line for outrageousness. See
___
Mosley, 965 F.2d at 910 (collecting formulations). Although this
______
standard lacks mathematical precision, we agree with Justice
Frankfurter that imprecision of this nature does not leave courts
without adequate guidance; rather, "[i]n dealing not with the
machinery of government but with human rights, the absence of
formal exactitude, or want of fixity of meaning, is not an
unusual or even regrettable attribute of constitutional
provisions." Rochin, 342 U.S. at 169.
______
____________________
outrageous misconduct. See Hampton, 425 U.S. at 491-95 (Powell,
___ _______
J. concurring).
6
The banner of outrageous misconduct is often raised but
seldom saluted. Even though one respected jurist contends that
the doctrine belongs in the dustbin of history, see United States
___ _____________
v. Miller, 891 F.2d 1265, 1271-73 (7th Cir. 1989) (Easterbrook,
______
J., concurring),5 case after case confirms its continued
existence. See Moran v. Burbine, 475 U.S. 412, 432 (1985) ("We
___ _____ _______
do not question that on facts more egregious than those presented
here police deception might rise to a level of a due process
violation."); United States v. Mosley, 965 F.2d 906, 909 (10th
______________ ______
Cir. 1992) (collecting cases from eleven circuits). Be that as
it may, the doctrine is moribund; in practice, courts have
rejected its application with almost monotonous regularity. See,
___
e.g., United States v. Barnett, 989 F.2d 546, 560 (1st Cir.
____ ______________ _______
1993), petition for cert. filed (June 28, 1993) (No. 93-5018);
________ ___ _____ _____
United States v. Lilly, 983 F.2d 300, 309-10 (1st Cir. 1992);
_____________ _____
United States v. Marino, 936 F.2d 23, 27 (1st Cir. 1991); United
_____________ ______ ______
States v. Rosen, 929 F.2d 839, 842 (1st Cir.), cert. denied, 112
______ _____ _____ ______
S. Ct. 77 (1991); United States v. McDowell, 918 F.2d 1004, 1008-
_____________ ________
09 (1st Cir. 1990); see also United States v. Panitz, 907 F.2d
___ ____ _____________ ______
1267, 1272-73 (1st Cir. 1990) (collecting pre-1990 First Circuit
____________________
5In Judge Easterbrook's view, the appropriateness of the
government's decision to supply drugs as part of an undercover
operation presents a "political" question that is
quintessentially nonjusticiable. Miller, 891 F.2d at 1272. With
______
respect, we think this conceptualization stretches the military
analogy too far. We adhere instead to the idea that "those
charged with th[e] investigative and prosecutorial duty should
not be the sole judges of when to utilize constitutionally
sensitive means in pursuing their tasks." United States v.
______________
United States District Court, 407 U.S. 297, 317 (1972).
____________________________
7
cases declining to invoke the doctrine); United States v. Bogart,
_____________ ______
783 F.2d 1428, 1434-38 (9th Cir.) (summarizing relevant case
law), vacated in part on other grounds sub nom. United States v.
__________________________________________ _____________
Wingender, 790 F.2d 802 (9th Cir. 1986); United States v. Warren,
_________ _____________ ______
747 F.2d 1339, 1342-43 & nn. 7-8 (10th Cir. 1984) (collecting
precedents from various circuits). Indeed, since the Supreme
Court decided Hampton, a federal appellate court has granted
_______
relief to a criminal defendant on the basis of the outrageous
misconduct defense only once. See United States v. Twigg, 588
___ _____________ _____
F.2d 373, 382 (3d Cir. 1978). The historical record makes it
clear, therefore, that the outrageous misconduct defense is
almost never successful.6
There are two competing visions of the doctrine's role.
One school of thought holds that the defense should be confined
to cases involving extreme physical, and possibly psychological,
abuse of a defendant. See United States v. Kelly, 707 F.2d 1460,
___ _____________ _____
1476 n.13 (D.C. Cir.) (per curiam) (collecting cases), cert.
_____
denied, 464 U.S. 908 (1983). A second school of thought holds
______
that outrageous misconduct may also function as a kind of
supplement to the entrapment defense, reserved for those cases
____________________
6In addition to Twigg, one court of appeals invoked the
_____
doctrine in an alternative holding, see United States v. Lard,
___ _____________ ____
734 F.2d 1290, 1296 (8th Cir. 1984), and another directed the
district court to determine whether outrageous misconduct should
be found on remand, see Bogart, 783 F.2d at 1438. A smattering
___ ______
of district courts have also applied the outrageous misconduct
doctrine to the defendant's advantage. See, e.g., United States
___ ____ _____________
v. Marshank, 777 F. Supp. 1507, 1524 (N.D. Cal. 1991); United
________ ______
States v. Gardner, 658 F. Supp. 1573, 1577 (W.D. Pa. 1987);
______ _______
United States v. Batres-Santolino, 521 F. Supp. 744, 751-52 (N.D.
_____________ ________________
Cal. 1981).
8
where law enforcement personnel become so overinvolved in a
felonious venture that they can fairly be said either to have
"creat[ed]" the crime or to have "coerc[ed]" the defendant's
participation in it. Mosley, 965 F.2d at 911-12; see also
______ ___ ____
Bogart, 783 F.2d at 1436-38. This case does not require us to
______
choose between these two conceptions of the doctrine.
III. APPLYING THE DOCTRINE
III. APPLYING THE DOCTRINE
Having traced the evolution of the doctrine of
outrageous misconduct, we proceed to consider its applicability
in this case. Although what transpired here fits neither of the
conventional patterns of outrageous misconduct described above,
the district court nonetheless ruled that furnishing the hefty
heroin sample (and then losing track of it) comes within the
doctrine's sweep. We conclude, for two independently sufficient
reasons, that the district court erred.
A. Outrageousness.
A. Outrageousness.
______________
"It is clear that the government may supply drugs to a
suspect in a drug investigation." Hampton, 425 U.S. at 491
_______
(Powell, J., concurring). When this occurs in the prototypical
case, an agent documents a malefactor's acceptance of a
government-supplied sample and then promptly arrests him. In
this scenario, even a large quantity of government-supplied drugs
will not raise judicial eyebrows, for the contraband is regained
coincident with the arrest. See, e.g., Barnett, 989 F.2d at 560
___ ____ _______
(declining to find outrageous misconduct where agent sold suspect
enough hydriodic acid to manufacture 18 kilos of methamphetamine
9
but recovered it promptly); United States v. Gianni, 678 F.2d
_____________ ______
956, 960 (11th Cir.) (similar; agents sold suspect 1150 lbs. of
marijuana but recovered it promptly), cert. denied, 459 U.S. 1071
_____ ______
(1982); United States v. Dunn, 608 F. Supp. 530, 531 (W.D.N.Y.
_____________ ____
1985) (similar; agent sold suspect one kilo of cocaine but
recovered it promptly).
The government's role in supplying drugs is more
problematic when the drugs are not recovered. Nonetheless,
several courts have held that providing a known addict small
quantities of drugs in order to facilitate the progress of an
undercover agent's work does not constitute outrageous
misconduct. See United States v. Harris, ___ F.2d ___, ___ (10th
___ _____________ ______
Cir. 1993) [No. 92-4001, 1993 WL 232155 at *5-*6]; United States
_____________
v. Barrera-Moreno, 951 F.2d 1089, 1092 (9th Cir. 1991), cert.
______________ _____
denied, 113 S. Ct. 417 (1992) & 113 S. Ct. 985 (1993); United
______ ______
States v. Ford, 918 F.2d 1343, 1349-50 (8th Cir. 1990).
______ ____
Common sense suggests that, where the target of the
investigation is a distributor rather than an addict, the
quantity of drugs needed to earn or retain the suspect's
confidence will likely be larger.7 It is, therefore,
unsurprising that courts generally have declined to find
outrageous misconduct in situations of this sort despite the
____________________
7We recognize that narcotics differ in many ways, including
size, weight, and potency; and that, therefore, a small amount of
a particular drug, say, heroin, may be much more lethal than a
larger amount of a different drug, say, marijuana. For ease in
reference, however, we use the term "quantity" throughout this
opinion as a proxy for dangerousness.
10
disappearance of fairly substantial quantities of government
supplied contraband. See, e.g., United States v. Valona, 834
___ ____ ______________ ______
F.2d 1334, 1344-45 (7th Cir. 1987) (declining to find misconduct
where the government disbursed, without recovering, a 3.5-gram
sample of cocaine while negotiating sales aggregating up to 35
kilos); United States v. Buishas, 791 F.2d 1310, 1314 (7th Cir.
_____________ _______
1986) (similar; government disbursed, without recovering, a 69-
gram sample of marijuana in the course of closing an 89-kilo
deal).
Although Valona and Buishas are structurally analogous
______ _______
to the case at hand, the government concedes that the quantity of
drugs given to Fuentes is, in absolute terms, unprecedented. The
question, then, is whether, at some point, the quantity of drugs
disbursed on the government's behalf may become so large that,
given all the attendant circumstances, the government's role
becomes qualitatively different, i.e., outrageous.
____
The court below devised a seven-part test and, applying
that test, determined the government's actions to be outrageous.
See Santana, 808 F. Supp. at 81-86. The court focused on (1) the
___ _______
type of drug furnished; (2) the sample's potency or purity; (3)
its relative size; (4) whether the defendant requested it; (5)
whether the drugs were recovered; (6) what likely happened to
them; and (7) whether the sample itself constitutes the corpus
______
delicti of the crime charged in the indictment.8 Id. at 81-82.
_______ ___
____________________
8In contrast, the relevant DEA guidelines, see supra note 1,
___ _____
suggest consideration of (1) the type and amount of the drug
contained in the sample; (2) the likelihood that the sample will
11
We appreciate the district court's effort to structure the
exercise of judicial discretion, and we realize that the court
did not intend its compendium to be exhaustive. See id. at 82.
___ ___
Nevertheless, we do not think that the inquiry into
outrageousness can usefully be broken down into a series of
discrete components. Almost by definition, the power of a court
to control prosecutorial excesses through resort to substantive
aspects of the due process clause is called into play only in
idiosyncratic situations and such situations are likely to be
highly ramified. Where facts are critically important and fact
patterns tend to be infinitely diverse, adjudication can often
best proceed on a case-by-case basis. The outrageousness defense
falls into this category. Thus, it is unproductive to force the
determination of outrageousness into a mechanical mode.
Let us be perfectly plain. We find that
outrageousness, by its nature, requires an ad hoc determination.
__ ___
We do not suggest, however, that the assessment should be wholly
unguided. The calculus must be rooted in the record, and it will
often be informed by the various factors enumerated in the
district court's test, the DEA's test, see supra note 8, and
___ _____
____________________
reach consumers; (3) the number and prominence of the suspects
implicated; (4) the type and amount of evidence needed to
complete the ongoing investigation; (5) the time required to do
so; and (6) the likelihood of obtaining such evidence. Although
the DEA's list, like the district court's list, contains factors
relevant to the seriousness of harm likely to be suffered by end
users, the DEA's list emphasizes, and the court's list slights,
the likelihood that the investigation will lead to the
prosecution of important drug dealers.
12
similar tests produced by other sources.9 At bottom, however,
outrageousness is a concept, not a constant. What shocks the
conscience in a given situation may be acceptable, though perhaps
grim or unpleasant, under a different set of circumstances.
Slashing a person's throat with a sharp knife may be an
unrelievedly outrageous course of conduct if one thinks in terms
of Jack the Ripper, helpless women, and the shadowy streets of
London; the same behavior will be thoroughly acceptable, however,
if the knife is a scalpel, the knife-wielder a skilled surgeon
performing a tracheotomy, the target a patient, and the venue an
operating room. Although we recognize that formulaic tests offer
administrative convenience and ease in application, we also
recognize that neither life nor law can always be made convenient
and easy. So here: there is simply no way to reduce the myriad
combinations of potentially relevant circumstances to a neat list
of weighted factors without losing too much in the translation.
Cf. Borden v. Paul Revere Life Ins. Co., 935 F.2d 370, 380 (1st
___ ______ __________________________
Cir. 1991) (discussing "outrageousness" in the context of tort
liability and concluding that "[t]here is no universal litmus
____________________
9See, e.g., United States v. Feinman, 930 F.2d 495, 498 (6th
___ ____ _____________ _______
Cir. 1991) (suggesting that a reviewing tribunal weigh (1) the
importance of the investigation, evidenced by the type of
criminal activity targeted, (2) whether the criminal enterprise
predated the investigation, (3) whether the investigator directed
or controlled the criminal activity, and (4) the investigation's
impact on the commission of the crime); United States v. Gardner,
_____________ _______
658 F. Supp. 1573, 1576-77 (W.D. Pa. 1987) (suggesting that a
reviewing tribunal weigh (1) the government's role in creating
the crime, (2) the illegality or immorality of the police
conduct, (3) the defendant's predisposition to commit the crime,
and (4) whether the investigation is aimed at preventing further
criminality).
13
test that a court can utilize to determine whether behavior is
extreme and outrageous").
In addition to relying on a tightly structured
formulation in an area of the law demanding flexibility, the
district court compounded its error by omitting from that
formulation a salient set of considerations: it disregarded the
nature and scope of the ongoing investigation. The
outrageousness vel non of a police officer's actions can only be
___ ___
evaluated by taking into account the totality of the relevant
circumstances. When the officer is on the trail of a criminal
enterprise, these circumstances include the identity of the
suspects, the gravity of past crimes, and the dangers foreseeably
attributable to the enterprise's uninterrupted progress
(including likely future crimes). In this instance, the
government had a solid basis to believe that Santana's network
could distribute up to 200 kilograms of heroin per month. Seen
in that light, it does not shock our collective conscience to
think that a lawman would dangle 13.3 grams of heroin as bait to
land such a large-scale ring, even though delivery of the sample
ran a palpable risk of ushering it into the marketplace.
The district judge refused to honor this argument,
which the magistrate described as setting "a big hook to catch a
big fish," for several reasons. We find none of them convincing.
First, the judge worried that the big hook/big fish approach
would remove any outer limit on "the quantity of drugs that the
government can introduce to society." Santana, 808 F. Supp. at
_______
14
83. It is a sufficient answer to this concern that, here, the
size of the sample was proportionate both to the perceived threat
posed by the ongoing criminal activity and to the exigencies of
the chase. Other cases, involving greater quantities of drugs or
materially different circumstances, need not be decided unless
and until they arise.
Second, the judge concluded that "the government's
conduct served only to increase the aggregate sum of heroin
available for consumption." Id. at 84. This statement, which we
___
read as a bid to repudiate the magistrate's implicit assessment
of costs and benefits, is highly questionable. Let us compare
two worlds. In the first world, the government distributes 13.3
grams of heroin, but Santana's network is put out of business.
In the second world, the government exercises greater restraint
in its undercover activities, but fails to gather enough evidence
to immobilize the ring. The aggregate supply of heroin will be
greater in the first world only if one is prepared to indulge the
unlikely assumption that some other equally skilled criminal
network will instantaneously pick up the slack.
Third, the judge, without saying so in haec verba,
____ _____
seemingly suggests that some situations cannot be analyzed in
terms of societal costs and benefits. See id. at 85; cf. Richard
___ ___ ___
C. Donnelly, Judicial Control of Informants, Spies, Stool
__________________________________________________
Pigeons, and Agents Provocateurs, 60 Yale L.J. 1091, 1111 (1951)
_________________________________
(denouncing "the sinister sophism that the end, when dealing with
known criminals or the 'criminal classes,' justifies the
15
employment of illegal means"). We do not share the district
court's discomfiture with means/ends rationality or what
amounts to the same thing cost/benefit analysis. At least when
the decisionmaker uses a common currency of exchange and operates
under conditions of reasonable certainty, cost/benefit analysis
is a perfectly legitimate mode of legal reasoning, frequently
employed by both courts and agencies. See generally Richard A.
___ _________
Posner, The Problems of Jurisprudence 105-08 (1990). Using such
_____________________________
an approach here does not strike us as either theoretically
unsound or fundamentally unfair. More important still, we can
identify no constitutional impediment to the government weighing
the risk of an immediate 13.3-gram increase in the heroin supply
against the potential benefit of diverting vast quantities of
heroin from the American market.
The district court's resistance to cost/benefit
analysis is carried to its logical conclusion by appellee
Fuentes. He maintains that no possible prosecutorial objective
can justify the distribution of so much heroin by the government.
But, since there is abundant precedent for distribution of drugs
by law enforcement agents mounting stings and other undercover
operations, see cases cited supra pp. 9-10, the only course of
___ _____
action compatible with Fuentes's argument would be to construct a
per se rule, drawing a bright line at some particular quantity of
___ __
drugs and forbidding lawmen to cross that line in dealing with
suspected drug traffickers. We regard a per se rule in this
___ __
16
context as unprecedented, unworkable,10 unwise, and thoroughly
uninviting. We, therefore, refuse to travel that road.
Saying that we reject the district court's objections
to the big hook/big fish metaphor is not tantamount to saying
that we unreservedly embrace the comparison. A hook, regardless
of its size, causes injury only to the fish that is caught. We
think that a more useful metaphor is that it takes a wide net to
catch a big fish. Of course, a net cast to catch a big fish
(thought to be predatory) might also catch hundreds of relatively
innocent little fish. But, if the big fish would have devoured
millions of little fish, even the most tender-hearted marine
biologist would be hard pressed to argue against the fisherman's
use of the net. In the final analysis, probing the magistrate's
metaphor for imprecisions does not assist appellees' cause, but,
rather, reinforces our conviction that the intuition underlying
the metaphor is sound.
We have trolled enough in these waters. We conclude
that, on the facts of this case, the district court erred in
discounting the import of the criminal enterprise's scope and the
magnitude of the threat that it posed. This error possesses
decretory significance: once the size of the sample is measured
in relative rather than absolute terms, the investigation
____________________
10We illustrate one of the many problems that such a per se
___ __
rule would present. Were we to draw such a line at, say, 10
grams of heroin, we would be handing criminals a foolproof way to
detect whether prospective new suppliers were actually government
agents: simply demand a sample equal to 11 or 12 grams of
heroin.
17
reviewed here is no longer unprecedented and the conduct in
question cannot plausibly be classified as outrageous.11
B. Misconduct Not Injuring Defendants.
B. Misconduct Not Injuring Defendants.
__________________________________
Generally speaking, an outrageous misconduct defense
can prosper only if a defendant's due process rights have been
___________
violated. The defense is normally not available in situations
where the government has injured only third parties or committed
a victimless gaffe. We would be compelled to reverse the ruling
below on this basis even if the government's deportment failed
the test of outrageousness.
In an early entrapment case, Justice Brandeis wrote:
"The prosecution should be stopped, not because some right of
th[e] defendant's] has been denied, but in order to protect the
Government. To preserve it from illegal conduct of its officers.
To protect the purity of its courts." Casey v. United States,
_____ _____________
276 U.S. 413, 425 (Brandeis, J., dissenting). The obvious
implication of this perspective with its emphasis on the rule
of law rather than on individual rights is that the state ought
not profit by its miscreancy, regardless of whether a charged
defendant has been wronged. Although the doctrinal view of
entrapment based on this philosophy never prevailed, see Russell,
___ _______
411 U.S. at 428-36, the Second Circuit subsequently flirted with
the same perspective in a different context. In an outrageous
____________________
11We do not totally reject the possibility, suggested by the
court below, that outrageous misconduct may be found apart from
situations in which the government has used brutality or induced
commission of a crime. We simply note that the case at hand does
not require us to explore this doctrinal frontier.
18
misconduct case decided on other grounds, Judge Friendly
expressed tentative support, in the abstract, for the view that
the government ought not reap prosecutorial success growing out
of the seeds of misconduct injuring third parties. See United
___ ______
States v. Archer, 486 F.2d 670, 676-77 (2d Cir. 1973).12 The
______ ______
court below believed this principle to be applicable here. See
___
Santana, 808 F. Supp. at 84-85. We do not agree.
_______
In our estimation, the Archer dictum is incompatible
______
with later pronouncements of the Supreme Court. The flagship
case is United States v. Payner, 447 U.S. 727 (1979). There, the
_____________ ______
government obtained evidence against a defendant by rifling a
third party's briefcase. Although no due process claim was
presented on appeal, the Court seized the occasion to address the
precise question of misconduct injuring third parties and adopted
a distinction first endorsed by the Hampton plurality:
_______
[E]ven if we assume that the unlawful
briefcase search was so outrageous as to
offend fundamental "`canons of decency and
fairness,'" Rochin v. California, 342 U.S.
______ __________
165, 169 (1952) . . . the fact remains that
"[t]he limitations of the Due Process Clause
. . . come into play only when the Government
____________________
12Two recent Second Circuit cases cite Archer in connection
______
with the proposition that courts "will closely examine those
cases in which the Government misconduct injures third parties in
some way." United States v. Thoma, 726 F.2d 1191, 1199 (2d
______________ _____
Cir.), cert. denied, 467 U.S. 1228 (1984); accord United States
_____ ______ ______ _____________
v. Chin, 934 F.2d 393, 400 (2d Cir. 1991). But neither panel
____
actually applied this principle, because no injury to third
parties had been established. By like token, in United States v.
_____________
Panet-Collazo, 960 F.2d 256 (1st Cir.), cert. denied, 113 S. Ct.
_____________ _____ ______
220 (1992), we were able to sidestep the issue because the heroin
sample provided by the government as part of the sting was not
used in a manner outrageously injurious to third parties. See
___
id. at 260.
___
19
activity in question violates some protected
right of the defendant." Hampton v. United
_________ _______ ______
States, supra, at 490 (plurality opinion).
______ _____
Payner, 447 U.S. at 737 n.9 (1979). This statement, to be sure,
______
is dictum but it bears the earmarks of deliberative thought
purposefully expressed. The statement is clear, pointed, and
subscribed to by a 6-3 majority of the Justices. It is also
prominent in its placement, appearing, as it does, in the
concluding footnote of a major opinion. What is more, the issue
that footnote 9 addressed had been thoroughly debated in the
recent past, the Payner dissent treated it as purporting to
______
establish a "standing" limitation, see id. at 749 n.15 (Marshall,
___ ___
J., dissenting), and the footnote's message has not been diluted
by any subsequent pronouncement. Carefully considered statements
of the Supreme Court, even if technically dictum, must be
accorded great weight and should be treated as authoritative
when, as in this instance, badges of reliability abound. See
___
McCoy v. Massachusetts Inst. of Technology, 950 F.2d 13, 19 (1st
_____ _________________________________
Cir. 1991) (concluding that "federal appellate courts are bound
by the Supreme Court's considered dicta almost as firmly as by
the Court's outright holdings, particularly when . . . a dictum
is of recent vintage and not enfeebled by any subsequent
statement") (collecting cases to like effect from other
circuits), cert. denied, 112 S. Ct. 1939 (1992); see also Charles
_____ ______ ___ ____
Alan Wright, The Law of the Federal Courts 58, at 374 (4th ed.
_____________________________
1983).
We need not decide whether Payner established a
______
20
limitation on standing in the strict sense of the word, or merely
signaled that defendants are highly unlikely to prevail when they
seek to vindicate the rights of third parties. In either event,
Payner makes manifest that, here, the trial court lacked
______
authority under the due process clause to dismiss a charge on the
basis that governmental misconduct caused conscience-shocking
harm to non-defendants. See United States v. Valdovinos-
___ ______________ ___________
Valdovinos, 743 F.2d 1436, 1437-38 (9th Cir. 1984) (per curiam)
__________
(rejecting an outrageous misconduct defense on the strength of
footnote 9 in a case in which government agents, trying to trap
professional middlemen, lured illegal immigrants to the U.S. only
to deport them), cert. denied, 469 U.S. 114 (1985); United States
_____ ______ _____________
v. Miceli, 774 F. Supp. 760, 770 (W.D.N.Y. 1991) (rejecting an
______
outrageous misconduct defense on the strength of footnote 9 in a
case in which a government investigator seduced the defendant's
ex-wife in order to gather incriminating information about the
defendant).
IV. SUPERVISORY POWER
IV. SUPERVISORY POWER
The district court grounded its dismissal of count 3 on
its supervisory power as well as on the due process clause. See
___
Santana, 808 F. Supp. at 86. In a reprise of an argument earlier
_______
advanced, see supra Part III(B), the government asserts that a
___ _____
federal court's supervisory power does not enable it to curb
misconduct that injures only third parties by dismissing charges
against uninjured defendants. We test this assertion.
The contours of a court's supervisory power are not
21
much in doubt. Under them, a federal court "may, within limits,
formulate procedural rules not specifically required by the
Constitution or the Congress." United States v. Hasting, 461
_____________ _______
U.S. 499, 505 (1983). The Hasting Court flagged three underlying
_______
purposes that can justify the use of supervisory power in
response to case-related misconduct, viz.: "to implement a
____
remedy for violation of recognized rights; to preserve judicial
integrity by ensuring that a conviction rests on appropriate
considerations validly before the jury; and finally, as a remedy
designed to deter illegal conduct." Id. (citations omitted).
___
While we have expressed the view that courts should be willing to
"consider invoking [their] supervisory powers to secure
enforcement of `better prosecutorial practice and reprimand of
those who fail to observe it,'" United States v. Osorio, 929 F.2d
_____________ ______
753, 763 (1st Cir. 1991) (citation omitted), we have repeatedly
cautioned that such powers must be used sparingly, see, e.g.,
___ ____
id.; United States v. Babb, 807 F.2d 272, 279 (1st Cir. 1986);
___ ______________ ____
United States v. Lieberman, 608 F.2d 889, 899 (1st Cir. 1979),
______________ _________
cert. denied, 444 U.S. 1019 (1980). Potent elixirs should not be
_____ ______
casually dispensed.
We do not believe that the circumstances of this case
warrant such strong medicine. Although resort to a court's
supervisory power has not been foreclosed altogether as a means
to remedy government misconduct not injuring the defendant, the
Supreme Court has plainly semaphored its likely disapproval in
several analogous contexts. For example, the Payner Court
______
22
concluded that "the supervisory power does not authorize a
federal court to suppress otherwise admissible evidence on the
ground that it was seized unlawfully from a third party not
before the court." Payner, 447 U.S. at 735. In reaching this
______
conclusion, the Court emphasized that such evidence could not be
suppressed under the Fourth Amendment, see Rakas v. Illinois, 439
___ _____ ________
U.S. 128, 133-38 (1978), and reasoned that the lower court's
choice of a different analytic framework did nothing to alter the
relative values assigned to the underlying interests. Payner,
______
447 U.S. at 736. The lesson that this portion of Payner teaches
______
is that, in a case-specific context, society's interest in
adjudicating guilt and innocence on full information outweighs
its interest in punishing governmental misconduct directed
against third parties.
The Court subsequently held that the supervisory power
could not be invoked to reverse a conviction in order to
castigate the prosecution for misconduct that did not prejudice
(as opposed to injure) the defendant.13 See Hasting, 461 U.S.
___ _______
at 505. Because the prosecutor's actions in Hasting constituted
_______
harmless error vis-a-vis the defendant, see id. at 507, no relief
___ ___
was warranted. The holding of Hasting replicates the message
_______
____________________
13Misconduct not injuring the defendant is a subset of
harmless error (which itself might be described as misconduct not
prejudicing the defendant). For our purposes, the two categories
may be fruitfully analyzed as one. The only salient difference
between them is that the larger set subsumes not only misconduct
that injures third persons and victimless misconduct, but also
subsumes misconduct that violates a defendant's rights without
affecting the outcome of his case.
23
sent by Payner, but it does so a fortiori: if society's interest
______ _ ________
in fully informed adjudication sometimes can outweigh its
interest in protecting the Fifth Amendment rights of defendants,
__________
then surely it can outweigh society's more generalized interest
in making law enforcement officers toe the line.
The reasoning of the Hasting Court is also instructive.
_______
As in Payner, the Court in Hasting reasoned that when courts
______ _______
exercise the supervisory power, they must respect the balance of
interests struck by conventional application of the legal
doctrines governing the particular problem in the particular
case. See id. at 505. Furthermore, the Hasting Court identified
___ ___ _______
three justifications, or goals, in service of which the
supervisory power might appropriately be invoked, see id. at 506-
___ ___
07; see also supra p. 21, and rested its holding in part on an
___ ____ _____
analysis of them. The Court concluded that none of these three
goals are significantly advanced when the error that is alleged
to constitute misconduct proves harmless, for concerns over
individual rights and the integrity of the judicial process are
less acute in all such cases. See id. at 506. The Court stated
___ ___
that the third doctrinal goal the deterrence of misconduct14
"is an inappropriate basis for reversal where . . . the
prosecutor's remark is at most an attenuated violation of
[defendant's right to remain silent] and where means more
____________________
14We highlight this goal because it not only constitutes the
linchpin of the district court's rationale for employing the
supervisory power in this case, but also serves as the mainstay
of the supporting arguments advanced by the appellees and by the
amici.
24
narrowly tailored to deter objectionable prosecutorial conduct
are available." Id.
___
Another case delineating limits on the supervisory
power is Bank of Nova Scotia v. United States, 487 U.S. 250
____________________ _____________
(1988). There, the Court ruled that, "as a general matter, a
district court may not dismiss an indictment for errors in grand
jury proceedings unless such errors prejudiced the defendants."
Id. at 254. In reaching this conclusion, the Court adverted to
___
Payner's point that value choices dictated by the resolution of
______
the underlying legal problem should not be affected by the source
from which an inquiring court draws its power. See id. at 255.
___ ___
The Court also reaffirmed Hasting's point that the rationales for
_______
invoking supervisory power are much weaker in the harmless error
context.15 See id. at 255-56.
___ ___
In keeping with the Supreme Court's teachings, this
court has repeatedly refused to sanction the deployment of
supervisory power in order to redress harmless error. See
___
Osorio, 929 F.2d at 763 (finding no nexus between the alleged
______
misconduct and any prejudice to the defendant); United States v.
_____________
Pacheco-Ortiz, 889 F.2d 301, 310 (1st Cir. 1989) (denying relief
_____________
when prejudice was not a "product" of alleged misconduct); Babb,
____
807 F.2d at 272; Lieberman, 608 F.2d at 899; see also United
_________ ___ ____ ______
____________________
15It is a short step, sideways rather than forward, from
Hasting to Bank of Nova Scotia. Hasting holds that the
_______ ______________________ _______
supervisory power may not be used to evade the constitutional
harmless error doctrine of Chapman v. California, 386 U.S. 18
_______ __________
(1957); Bank of Nova Scotia holds that the supervisory power may
___________________
not be used to evade the less searching harmless error inquiry
mandated by Fed. R. Crim. P. 52(a).
25
States v. Hastings, 847 F.2d 920, 927 (1st Cir.), cert. denied,
______ ________ _____ ______
488 U.S. 925 (1988). We think this line of cases adequately
evinces our institutional belief that, taken together, Payner,
______
Hasting, and Bank of Nova Scotia form a trilogy admonishing
_______ _____________________
federal courts to refrain from using the supervisory power to
conform executive conduct to judicially preferred norms by
dismissing charges, absent cognizable prejudice to a particular
defendant.16 Accord United States v. Williams, 874 F.2d 968,
______ ______________ ________
976 n.23 (5th Cir. 1989). Here, appellees sustained no
redressable injury attributable to governmental misconduct.
Accordingly, the district court erred as a matter of law when it
invoked supervisory power to dismiss count 3 of the indictment.
Before departing from these shores, we pause to add a
qualification: the use of supervisory power to dismiss an
indictment, in the absence of injury to the defendant, may not be
entirely a dead letter. The Court's reasoning in Hasting may be
_______
read to leave open the possibility that the goal of deterring
future misconduct would justify using the supervisory power to
redress conduct not injuring defendants if the conduct is plainly
improper, indisputably outrageous, and not redressable through
the utilization of less drastic disciplinary tools. See Hasting,
___ _______
____________________
16The Second Circuit has gone even further, reading the
Supreme Court's cases to suggest that "the federal judiciary's
supervisory powers over prosecutorial activities that take place
outside the courthouse is extremely limited, if it exists at
all." United States v. Lau Tung Lam, 714 F.2d 209, 210 (2d
______________ _____________
Cir.), cert. denied, 464 U.S. 942 (1983). Because the case at
_____ ______
bar does not require that we probe the ramifications of this
suggestion, we take no view of it.
26
461 U.S. at 506. Be that as it may, we leave the qualification's
fate and dimensions for another day, as this is plainly not such
a case.
V. CONCLUSION
V. CONCLUSION
In summary, the orphan doctrine of outrageous
misconduct finds no nurturing home on the facts of this case
because the objects of the government's ongoing investigation
satisfactorily justified whatever harm stemmed from the delivery
(and subsequent loss) of a large heroin sample, and because, in
any event, that harm was not incurred by the appellees
themselves. In like manner, because the trial court
overestimated the reach of its supervisory power in cases of
misconduct not injuring defendants, its alternative rationale
crumbles. If there are exceptions to the general rules that we
have elucidated a matter on which we do not opine they are
assuredly not triggered by this case. Hence, the court lacked a
sufficient legal basis for dismissing count 3 of the indictment.
We need go no further. Although the effect of our
ruling is to uphold the government's tactics in this case, we
remain secure in the knowledge that, despite restrictions
hobbling the outrageous misconduct doctrine, law enforcement
practices are subject to a wide range of specific "constitutional
and statutory limitations and to judicially fashioned rules to
enforce those limitations." Russell, 411 U.S. at 435; cf.
_______ ___
Hasting, 461 U.S. at 506 n.5 (illustrating more narrowly tailored
_______
means to punish prosecutorial misconduct). Moreover, the
27
outrageous misconduct doctrine, no matter how cramped its
confines, is not entirely mummified. Should the occasion and the
necessity arise, we continue to believe that the law will prove
itself adequate to the task of preventing the government from
going too far. In the war on crime, as in conventional warfare,
some tactics simply cannot be tolerated by a civilized society.
Reversed.
Reversed.
________
28
Related
Casey v. United States
276 U.S. 413 (Supreme Court, 1928)
Sorrells v. United States
287 U.S. 435 (Supreme Court, 1932)
Rochin v. California
342 U.S. 165 (Supreme Court, 1952)
Kinsella v. United States Ex Rel. Singleton
361 U.S. 234 (Supreme Court, 1960)
Chapman v. California
386 U.S. 18 (Supreme Court, 1967)
United States v. United States District Court for the Eastern District of Michigan
407 U.S. 297 (Supreme Court, 1972)
United States v. Russell
411 U.S. 423 (Supreme Court, 1973)
Hampton v. United States
425 U.S. 484 (Supreme Court, 1976)
United States v. Payner
447 U.S. 727 (Supreme Court, 1980)
Trans World Airlines, Inc. v. Thurston
469 U.S. 111 (Supreme Court, 1985)
Moran v. Burbine
475 U.S. 412 (Supreme Court, 1986)
Bank of Nova Scotia v. United States
487 U.S. 250 (Supreme Court, 1988)
United States v. Norman Archer
486 F.2d 670 (Second Circuit, 1973)
Fed. Sec. L. Rep. P 97,167 United States of America v. Benjamin Lieberman, United States of America v. Jack H. Shapiro
608 F.2d 889 (First Circuit, 1980)
United States v. Richard Kelly
707 F.2d 1460 (D.C. Circuit, 1983)
United States v. Lau Tung Lam, A/K/A "Ah Tong,"
714 F.2d 209 (Second Circuit, 1983)
United States v. William L. Thoma
726 F.2d 1191 (Seventh Circuit, 1984)
United States v. Pete Woodrum Lard and Lloyd Dean Rigsby
734 F.2d 1290 (Eighth Circuit, 1984)
United States v. Clemente Valdovinos-Valdovinos
743 F.2d 1436 (Ninth Circuit, 1985)
United States v. David W. Warren
747 F.2d 1339 (Tenth Circuit, 1984)
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