23-6107 United States v. Cristobal
UNITED STATES COURT OF APPEALS FOR THE SECOND CIRCUIT
SUMMARY ORDER
RULINGS BY SUMMARY ORDER DO NOT HAVE PRECEDENTIAL EFFECT. CITATION TO A SUMMARY ORDER FILED ON OR AFTER JANUARY 1, 2007, IS PERMITTED AND IS GOVERNED BY FEDERAL RULE OF APPELLATE PROCEDURE 32.1 AND THIS COURT’S LOCAL RULE 32.1.1. WHEN CITING A SUMMARY ORDER IN A DOCUMENT FILED WITH THIS COURT, A PARTY MUST CITE EITHER THE FEDERAL APPENDIX OR AN ELECTRONIC DATABASE (WITH THE NOTATION “SUMMARY ORDER”). A PARTY CITING TO A SUMMARY ORDER MUST SERVE A COPY OF IT ON ANY PARTY NOT REPRESENTED BY COUNSEL.
At a stated term of the United States Court of Appeals for the Second Circuit, held at the Thurgood Marshall United States Courthouse, 40 Foley Square, in the City of New York, on the 8th day of April, two thousand twenty-four.
PRESENT:
DENNIS JACOBS, RICHARD J. SULLIVAN, EUNICE C. LEE, Circuit Judges. _____________________________________
UNITED STATES OF AMERICA,
Appellee,
v. No. 23-6107
PURIFICACION CRISTOBAL,
Defendant-Appellant. * _____________________________________
* The Clerk of Court is respectfully directed to amend the official case caption as set forth above. For Defendant-Appellant: JONATHAN A. ROSENBERG, Rosenberg Law Firm, Brooklyn, NY.
For Appellee: DEREK WIKSTROM (Kyle A. Wirshba, Jun Xiang, David Abramowicz, on the brief), Assistant United States Attorneys, for Damian Williams, United States Attorney for the Southern District of New York, New York, NY.
Appeal from a judgment of the United States District Court for the Southern
District of New York (Katherine Polk Failla, Judge).
UPON DUE CONSIDERATION, IT IS HEREBY ORDERED,
ADJUDGED, AND DECREED that the January 25, 2023 judgment of the district
court is AFFIRMED.
Purificacion Cristobal, a nurse practitioner and the sole medical professional
at a clinic in the Bronx, appeals from a judgment of conviction following a jury
trial in which she was found guilty of one count of conspiracy to distribute
oxycodone, in violation of 21 U.S.C. § 846, and two counts of distributing and
possessing with intent to distribute oxycodone, in violation of 21 U.S.C.
§§ 841(a)(1) and (b)(1)(C). Following the jury’s verdict, the district court denied
Cristobal’s motion for a judgment of acquittal pursuant to Federal Rule of
Criminal Procedure 29 or, in the alternative, for a new trial pursuant to Federal
2 Rule of Criminal Procedure 33. The district court thereafter sentenced Cristobal
to concurrent terms of eighty-four months’ imprisonment on each of the three
counts, to be followed by three years’ supervised release. On appeal, Cristobal
raises a litany of challenges to her conviction and sentence, which we address in
turn. We assume the parties’ familiarity with the underlying facts, procedural
history, and issues on appeal.
I. Sufficiency of the Evidence
Cristobal first argues that the district court should have granted her motion
for a judgment of acquittal because the government failed to prove her subjective
intent to distribute controlled substances without authorization, as is required by
section 841. We disagree.
“We review preserved claims of insufficiency of the evidence de novo.”
United States v. Capers, 20 F.4th 105, 113 (2d Cir. 2021) (internal quotation marks
omitted). But even under de novo review, “defendants face a heavy burden,”
United States v. Ho, 984 F.3d 191, 199 (2d Cir. 2020) (internal quotation marks
omitted), because we must view the evidence “in the light most favorable to the
government . . . credit[ing] every inference that the jury might have drawn in
favor of the government.” United States v. Atilla, 966 F.3d 118, 128 (2d Cir. 2020)
3 (internal quotation marks omitted). Ultimately, “[a] judgment of acquittal is
warranted only if the evidence that the defendant committed the crime alleged is
nonexistent or so meager that no reasonable jury could find guilt beyond a
reasonable doubt.” United States v. Martoma, 894 F.3d 64, 72 (2d Cir. 2017)
(internal quotation marks omitted).
Section 841 makes it unlawful for any person to “knowingly or
intentionally” “distribute[] or dispense” a controlled substance “[e]xcept as
authorized.” 21 U.S.C. § 841(a). As provided by federal regulation, licensed
practitioners – such as Cristobal – are authorized to issue prescriptions for
controlled substances, but only if these prescriptions are issued “for a legitimate
medical purpose” and “in the usual course of . . . professional practice.” 21 C.F.R.
§ 1306.04(a). In Ruan v. United States, the Supreme Court held that, when a
defendant is authorized to prescribe controlled substances, she may not be
convicted under section 841 unless the government “prove[s] beyond a reasonable
doubt that the defendant knew that . . . she was acting in an unauthorized
manner.” 597 U.S. 450, 454 (2022).
At the same time, and as Cristobal concedes, Ruan reaffirmed that the
government can prove the requisite knowledge “through circumstantial
4 evidence.” Id. at 467; see also United States v. Heras, 609 F.3d 101, 106 (2d Cir. 2010)
(“The law has long recognized that criminal intent may be proved by
circumstantial evidence alone.”). Moreover, to prove subjective intent, the
government can refer to, and compare a defendant’s conduct against, “objective
criteria such as ‘legitimate medical purpose’ and ‘usual course’ of ‘professional
practice.’” Ruan, 597 U.S. at 467 (quoting 21 C.F.R. § 1306.04(a)). “[T]he more
unreasonable a defendant’s asserted beliefs or misunderstandings are, especially
as measured against objective criteria, the more likely the jury will find that the
[g]overnment has carried its burden of proving knowledge.” Id. (alterations and
internal quotation marks omitted).
Against this legal backdrop, Cristobal asserts that the government failed to
carry its burden on section 841’s intent element because the evidence
demonstrated that she genuinely believed that she was issuing oxycodone
prescriptions for legitimate medical reasons in the usual course of her professional
practice. But Cristobal made these same arguments to the jury, which clearly
rejected them. See United States v. Clarke, 979 F.3d 82, 91 (2d Cir. 2020). We must
“defer to the jury’s determination of the weight of the evidence and the credibility
of the witnesses, and to the jury’s choice of the competing inferences that can be
5 drawn from the evidence.” United States v. Landesman, 17 F.4th 298, 320 (2d Cir.
2021) (internal quotation marks omitted).
At trial, the jury heard ample evidence from which it reasonably could have
concluded that Cristobal knew she was prescribing oxycodone without any
medical purpose and outside the course of professional practice. For example,
multiple witnesses testified to telling Cristobal that her patients were selling or
abusing the drugs she prescribed. Christian Ohaeri, a cooperating coconspirator
and pharmacist who often filled prescriptions written by Cristobal, testified to
warning Cristobal in October 2019 that the majority of her patients were selling
the drugs she was prescribing. Destiny White and Daniella LoCicero, whom
Cristobal hired as receptionists after first treating them as patients, likewise
testified that the clinic was regularly filled with visibly high patients waiting to
receive their prescriptions. Indeed, White testified that she repeatedly informed
Cristobal that these waiting patients appeared to be high; she also pressed
Cristobal to set up a drug testing program to confirm that oxycodone patients were
not selling their prescribed drugs or taking unprescribed narcotics. Despite these
warnings, the evidence reflected that Cristobal continued in her prescribing
practices.
6 The government also introduced evidence that Cristobal dramatically
deviated from the ordinary practices of other medical providers, offering
circumstantial support of her intent to act without authorization. See Ruan, 597
U.S. at 467. This evidence reflected that, among other things, Cristobal allowed
her patients to choose between narcotics according to their preference and
regularly issued prescriptions without conducting physical examinations (and, in
fact, lacked the medical equipment necessary to perform them). In addition,
Cristobal routinely prescribed a combination of oxycodone, Xanax, and Adderall
– a rarely prescribed trifecta of drugs that each treat different conditions and are
dangerous to take together, but when used in combination, produce an intense
high and, as a result, have high combined street values. Expert testimony
established that these practices represented deviations from the usual course of
professional practice.
Other unusual circumstances that supported a finding of subjective intent
included Cristobal’s practice of charging clients, who often paid in cash, by the
prescription; her withholding of prescriptions based on patients’ inability to pay;
and her instructions that patients avoid filling prescriptions at large pharmacies
where oxycodone prescriptions were more likely to be closely scrutinized.
7 Cristobal also required her patients to sign forms in which they promised not to
disclose any information about Cristobal to law enforcement and which warned
that doing so “w[ould] be deemed and construed as entrapment.” Suppl. App’x
at 91–92.
Based on this considerable evidence, there is no question that a reasonable
jury could have found beyond a reasonable doubt that Cristobal knew that she
was unlawfully prescribing oxycodone. See United States v. Moore, 423 U.S. 122,
142–43 (1975) (affirming sufficiency of evidence where the defendant gave patients
“inadequate physical examinations or none at all,” “ignored the results of the tests
he did make,” “took no precautions against . . . misuse and diversion,” “did not
regulate the dosage at all, prescribing as much and as frequently as the patient
demanded,” and charged by the “number of tablets desired” instead of “for
medical services rendered”); see also United States v. Maye, 649 F. App’x 15, 16 (2d
Cir. 2016) (affirming sufficiency of evidence based on “ample circumstantial
evidence,” including expert testimony about the “usual course of medical
practice” and evidence that defendant failed to conduct patient examinations or
obtain medical records).
8 II. Expert Testimony
Cristobal also contends that the district court erred by permitting the
government’s expert witness, Dr. Christopher Gharibo, to offer legal conclusions
regarding the standards of care that applied to doctors prescribing controlled
substances in New York. We review a district court’s decision to admit evidence,
including expert testimony, for abuse of discretion. 1 United States v. Romano, 794
F.3d 317, 330 (2d Cir. 2015). A district court abuses its discretion when its decision
“rests on an error of law” or “clearly erroneous factual finding,” or when the
decision “cannot be located within the range of permissible decisions.” United
States v. Kaplan, 490 F.3d 110, 118 (2d Cir. 2007) (internal quotation marks omitted).
We cannot agree that Dr. Ghabiro provided an impermissible legal
conclusion when he testified that regulations in New York state require
practitioners to conduct physical examinations before prescribing oxycodone.
While Cristobal is correct that “[a]s a general rule,” “an expert’s testimony on
issues of law is inadmiss[i]ble,” we have allowed experts to testify on relevant
regulations and industry standards as a basis to evaluate a defendant’s conduct
and intent. United States v. Bilzerian, 926 F.2d 1285, 1294 (2d Cir. 1991); see also
1 For the purposes of this order, we assume – without deciding – that Cristobal’s counsel lodged a timely objection at trial to the admission of this expert testimony.
9 United States v. McElroy, 910 F.2d 1016, 1023–24 (2d Cir. 1990). And as Ruan makes
clear, evidence as to the “‘usual course’ of ‘professional practice’” – when
considered in conjunction with the defendant’s conduct – is relevant to the jury’s
evaluation of the defendant’s subjective intent. See Ruan, 597 U.S. at 467.
Here, Dr. Gharibo testified that practitioners acting in the usual course of
professional practice conduct physical examinations before prescribing
oxycodone, and cited a New York state regulatory requirement. In doing so, Dr.
Gharibo did not “suggest to the jury that it could find [Cristobal] guilty simply by
reason of [her] violation of the regulation,” McElroy, 910 F.2d at 1023, nor did he
express any opinion as to Cristobal’s own state of mind, see United States v.
DiDomenico, 985 F.2d 1159, 1164 (2d Cir. 1993). Accordingly, we cannot say that
the district court abused its discretion in allowing this evidence. 2
III. Jury Instructions
Next, Cristobal contends that the district court erroneously instructed the
jury to apply an objective, rather than subjective, standard of intent in violation of
2 Cristobal asserts, on reply, that Dr. Gharibo was not qualified as an expert to offer testimony on the “New York regulatory requirements governing psychiatric practitioners” like herself. Reply Br. at 1–2. Because she did not make this argument in her principal brief, we deem it forfeited and do not address it here. See JP Morgan Chase Bank v. Altos Hornos de Mexico, S.A. de C.V., 412 F.3d 418, 428 (2d Cir. 2005) (“[A]rguments not made in an appellant’s opening brief are [forfeited] even if the appellant pursued those arguments in the district court or raised them in a reply.”).
10 Ruan. Although Cristobal proposed her own jury charge on the requisite intent,
she did not object to the district court’s proposed instruction at the charge
conference. Accordingly, we review this challenge for plain error. See United
States v. Crowley, 318 F.3d 401, 412–14 (2d Cir. 2003). To prevail on plain-error
review, an appellant must demonstrate that the error “is clear or obvious,”
“affected the appellant’s substantial rights,” and “seriously affects the fairness,
integrity[,] or public reputation of judicial proceedings.” United States v.
McCrimon, 788 F.3d 75, 78 (2d Cir. 2015) (internal quotation marks omitted).
In charging the jury on the element of intent, the district court instructed
that the government must prove that Cristobal “distributed or dispensed, or
caused to be distributed or dispensed, oxycodone knowing or intending that the
prescription was not issued for a legitimate medical purpose by an individual
practitioner acting in the usual course of her professional practice.” Suppl. App’x
at 224 (emphasis added). The district court went on to define the terms
“legitimate medical purpose” and “usual course of professional practice” to mean
“acting in accordance with a standard of medical practice generally recognized
and accepted in the State of New York.” Id.
11 Contrary to Cristobal’s assertions, this instruction comports with Ruan’s
requirements. As noted above, a practitioner violates section 841 when she
knowingly issues prescriptions in an unauthorized manner. And, as the Ruan
Court recognized, the scope of a practitioner’s prescribing authority is defined by
federal regulation with “reference to objective criteria such as ‘legitimate medical
purpose’ and ‘usual course’ of ‘professional practice.’” 597 U.S. at 467 (quoting
21 C.F.R. § 1306.04(a)). We find no error, let alone plain error, in the district
court’s instructions discussing these objective criteria by reference to the medical
practice standards of New York, the state in which Cristobal was licensed to
practice.
More fundamentally, the district court did not incorrectly transform the
subjective intent standard into an objective one. To the contrary, the district court
repeatedly told the jury that the government had to prove not just that Cristobal
acted without a legitimate medical purpose, but that she knew she was doing so.
See Suppl. App’x at 220–27; Ruan, 597 U.S. at 457–61; see also United States v. Al
Kassar, 660 F.3d 108, 127 (2d Cir. 2011) (“[W]e examine not only the specific
language that the defendant challenges but also the instructions as a whole to see
if the entire charge delivered a correct interpretation of the law.” (internal
12 quotation marks omitted)). Because the district court correctly instructed the jury
that it must find Cristobal’s subjective consciousness of guilt in order to convict,
her challenge to the jury instruction fails.
IV. Brady Violations
Cristobal also asserts that a new trial is warranted because the government
violated its obligations under Brady v. Maryland, 373 U.S. 83 (1963), in two distinct
ways. First, she contends that the government did not timely disclose
information that could have been used to impeach Ohaeri — namely, his guilty
plea to fraud involving the writing of fake prescriptions in Cristobal’s name and a
packet of information containing all prescriptions that he wrote in her name.
Second, Cristobal argues that the government waited until mid-trial to disclose
that the hard-copy patient files seized from Cristobal’s clinic had been
incompletely scanned, so that the electronic productions of those files previously
made by the government did not accurately reflect their full contents. After
discovering the scanning error mid-trial, the government reviewed the hard-copy
files and promptly produced electronic versions of 143 additional pages, taken
from 95 of Cristobal’s 612 patient files, which had not previously been digitized or
shared electronically with defense counsel.
13 To establish a Brady violation, “a defendant must show that: (1) the
[g]overnment, either willfully or inadvertently, suppressed evidence; (2) the
evidence at issue is favorable to the defendant; and (3) the failure to disclose this
evidence resulted in prejudice.” United States v. Coppa, 267 F.3d 132, 140 (2d Cir.
2001); see id. at 135 (explaining that “favorable evidence” refers to both exculpatory
and impeachment evidence). Because Cristobal raised these claims in her motion
for a new trial under Rule 33, we review the district court’s denial of that motion
for abuse of discretion. See United States v. Hunter, 32 F.4th 22, 30 (2d Cir. 2022).
As to her first Brady claim, Cristobal has failed to show that the government
suppressed impeachment material relating to Ohaeri. For starters, the record
reflects that materials regarding Ohaeri’s cooperation and guilty plea were
disclosed in real time as they were generated or shortly thereafter. Moreover, as
the government explains (and Cristobal does not dispute), the packet of
information that Cristobal describes consisted of additional information regarding
Ohaeri’s prescription-filling history that defense counsel requested after the start
of trial, which the government did not possess at the time but obtained from
Ohaeri’s counsel and immediately disclosed. The government had no obligation
to discover and collect materials that it did not possess. See United States v.
14 Avellino, 136 F.3d 249, 255 (2d Cir. 1998) (limiting Brady to evidence “that is known
to the prosecutor”); see also United States v. Hutcher, 622 F.2d 1083, 1088 (2d Cir.
1980) (“Clearly the government cannot be required to produce that which it does
not control and never possessed or inspected.” (internal quotation marks
omitted)). In any case, even assuming that these materials were suppressed,
Cristobal does not meaningfully explain how they were favorable to her, or how
any belated disclosure of the materials resulted in prejudice. See Coppa, 267 F.3d
at 140; see also id. at 142 (“[W]e have never interpreted due process of law as
requiring more than that Brady material must be disclosed in time for its effective
use at trial.”).
Cristobal’s second Brady claim – pertaining to the improperly scanned
patient files – is also unavailing. As Cristobal acknowledged and as the district
court found, the physical files underlying this Brady claim were available for
defense counsel’s review for more than a year prior to the start of trial. And
again, Cristobal does not explain how these files were favorable to her case. She
does not identify any pages, individually or in the aggregate, that she would have
used at trial, nor does she assert that the government relied on the inclusion or
omission of these pages to her detriment. See United States v. Montague, 67 F.4th
15 520, 538–39 (2d Cir. 2023) (rejecting Brady claim where defendant “d[id] not show
that the record was favorable to him because it was exculpatory or impeaching”
(alterations and internal quotation marks omitted)). Moreover, Cristobal fails to
meaningfully articulate how the belated disclosure of these pages gives rise to a
“reasonable probability” that the outcome of the case was affected. See Coppa, 267
F.3d at 135, 143. She omits mention of the steps taken during trial to mitigate any
prejudice from the mid-trial disclosure; the government, for example, refrained
from using any of the previously unscanned documents in its case-in-chief, unless
such inclusion would be favorable to Cristobal.
Accordingly, the district court did not abuse its discretion in determining
that the government’s mid-trial disclosure did not warrant a new trial in this case.
V. Drug Quantity Calculation
Finally, Cristobal argues that the district court impermissibly speculated as
to the total number of her unlawful oxycodone prescriptions when it calculated
her base offense level under the Sentencing Guidelines. We review the
procedural reasonableness of a sentence “under a deferential abuse-of-discretion
standard,” United States v. Yilmaz, 910 F.3d 686, 688 (2d Cir. 2018), and have held
that a “district court errs procedurally when it fails to calculate (or improperly
16 calculates) the Sentencing Guidelines range,” United States v. Alvarado, 720 F.3d
153, 157 (2d Cir. 2013) (internal quotation marks omitted). At sentencing, the
government bears the burden of proving drug quantity by a preponderance of the
evidence, see United States v. Colon, 961 F.2d 41, 43 (2d Cir. 1992), and we review
the district court’s drug-quantity calculation for clear error, see United States v.
Jones, 531 F.3d 163, 176 (2d Cir. 2008).
Cristobal contends that the district court improperly assumed, based on her
convictions for unlawful distribution of oxycodone on two occasions, that some or
all of the prescriptions she issued in 2019 and 2020 were unlawful. But in fact, the
district court took the opposite approach. In reaching its drug quantity
calculation, the district court examined “specific evidence” introduced at trial,
including “drug records” in the form of prescription data and “live testimony”
from numerous coconspirators about Cristobal’s prescribing practices. See United
States v. Shonubi, 103 F.3d 1085, 1089–92 (2d Cir. 1997); see also United States v.
Blount, 291 F.3d 201, 215 (2d Cir. 2002) (“In making [a drug quantity] estimate, the
court has broad discretion to consider all relevant information.”). For example,
the district court considered that approximately half of Cristobal’s patients who
received oxycodone prescriptions had no MRIs or other clinical documentation to
17 substantiate their prescriptions, and that the percentage of Cristobal’s oxycodone
prescriptions significantly increased during the relevant period, while
prescriptions for controlled substances outside of the oxycodone-Xanax-Adderall
combination significantly decreased.
In the end, the district court adopted a conservative approach and found
only one third of Cristobal’s prescriptions to be unlawful, despite expressly
recognizing that the evidence supported such a finding as to all prescriptions
identified by the government. Based on the record, we cannot conclude that the
district court’s calculation was clearly erroneous.
* * *
We have considered Cristobal’s remaining arguments and find them to be
without merit. Accordingly, we AFFIRM the judgment of the district court.
FOR THE COURT: Catherine O’Hagan Wolfe, Clerk of Court