23-7909-cr United States v. Spain
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 13th day of March, two thousand twenty-five.
PRESENT: JOHN M. WALKER, JR., RICHARD C. WESLEY, JOSEPH F. BIANCO, Circuit Judges. _____________________________________
UNITED STATES OF AMERICA,
Appellee,
v. 23-7909-cr
ISAIAH SPAIN, AKA Q,
Defendant-Appellant. _____________________________________
FOR APPELLEE: Katherine A. Gregory, Assistant United States Attorney, for Michael DiGiacomo, Interim United States Attorney for the Western District of New York, Buffalo, New York.
FOR DEFENDANT-APPELLANT: Brendan White, White & White, New York, New York. Appeal from an amended judgment of the United States District Court for the Western
District of New York (Richard J. Arcara, Judge).
UPON DUE CONSIDERATION, IT IS HEREBY ORDERED, ADJUDGED, AND
DECREED that the amended judgment of the district court, entered on November 20, 2023, is
AFFIRMED.
Defendant-Appellant Isaiah Spain appeals from the district court’s amended judgment of
conviction following his guilty plea to a one-count superseding information, charging him with
conspiracy to possess with intent to distribute, and to distribute, ten grams or more of butyryl
fentanyl, heroin, fentanyl, and furanyl fentanyl, in violation of 21 U.S.C. §§ 846, 841(a)(1), and
841(b)(1)(B). The conviction arose from Spain’s participation, between 2016 and 2019, in a
conspiracy to distribute narcotics—including heroin, fentanyl, butyryl fentanyl, and furanyl
fentanyl—which resulted in a number of drug overdoses, two of which were fatal. On appeal,
Spain argues that his guilty plea must be vacated because, during his guilty plea proceeding, the
presiding magistrate judge failed to advise him of his right to appointed counsel, in violation of
Federal Rule of Criminal Procedure 11(b)(1)(D). 1 We assume the parties’ familiarity with the
underlying facts, procedural history, and issues on appeal, to which we refer only as necessary to
explain our decision to affirm.
On January 23, 2023, during Spain’s guilty plea proceeding, the magistrate judge asked
Spain a series of questions, pursuant to Rule 11, to determine whether the court should accept his
guilty plea, including whether Spain understood that he was “entitled to be represented at all stages
of this case[,] including the trial[,] by an attorney.” App’x at 96. It is uncontested that the
1 Pursuant to Rule 11(b)(1)(D), “the court must inform the defendant of, and determine that the defendant understands, . . . [his] right to be represented by counsel—and if necessary[,] have the court appoint counsel—at trial and at every other stage of the proceeding.” 2 magistrate judge did not inform Spain at this plea proceeding that he had a right to appointed
counsel if he could not afford to retain an attorney on his own. At the conclusion of the proceeding,
the magistrate judge found that Spain’s plea of guilty to the superseding information was knowing
and voluntary and recommended that the district court accept the plea. The district court
subsequently accepted the guilty plea and sentenced Spain principally to 250 months’
imprisonment, consistent with the terms of the plea agreement entered into by the parties pursuant
to Rule 11(c)(1)(C). This appeal followed.
We review a challenge to a conviction on the grounds that a district court allegedly failed
to comply with Rule 11 for plain error where, like here, the defendant did not raise an objection to
the district court. See United States v. Torrellas, 455 F.3d 96, 103 (2d Cir. 2006). To demonstrate
plain error, a defendant must establish that “(1) there is an error; (2) the error is clear or obvious,
rather than subject to reasonable dispute; (3) the error affected the [defendant]’s substantial rights;
and (4) the error seriously affects the fairness, integrity or public reputation of judicial
proceedings.” United States v. Balde, 943 F.3d 73, 96 (2d Cir. 2019). A Rule 11 violation affects
a defendant’s substantial rights where “there is ‘a reasonable probability that, but for the error, he
would not have entered the plea.’” United States v. Vaval, 404 F.3d 144, 151 (2d Cir. 2005)
(quoting United States v. Dominguez Benitez, 542 U.S. 74, 76 (2004)). In other words, a defendant
must demonstrate that “the district court’s error had an effect on his decision to plead guilty.”
United States v. Harrison, 241 F.3d 289, 293 (2d Cir. 2001). Moreover, “an appellate court
conducting plain-error review may consider the entire record—not just the record from the
particular proceeding where the error occurred.” Greer v. United States, 593 U.S. 503, 511 (2021).
Spain contends that, although the magistrate judge informed him of his right to counsel
during the guilty plea proceeding, the magistrate judge nevertheless plainly erred by not advising
3 him of his right to appointed counsel, in violation of Rule 11(b)(1)(D). More specifically, Spain
argues that the prolonged plea negotiation process, which took several years, and the seriousness
of the charges he faced indicated that there was a reasonable probability that he would have gone
to trial, but because neither he nor his family could continue to pay for retained counsel, he chose
to enter into the plea deal. Thus, Spain asserts that, had the magistrate judge reminded him of his
right to appointed counsel at the guilty plea proceeding, he would not have entered his guilty plea,
and instead would have gone to trial. We find these arguments unpersuasive.
As an initial matter, because the record indicates that, long before his guilty plea
proceeding, Spain was aware that he was entitled to counsel at all stages of his case and to
appointed counsel if he could not afford to hire an attorney, there is no reasonable probability that
the magistrate judge’s failure to remind him of that right at the guilty plea proceeding affected his
decision to plead guilty. In particular, at his initial appearance and arraignment on April 5, 2019,
in connection with the thirteen-count indictment filed against him, the magistrate judge advised
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23-7909-cr United States v. Spain
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 13th day of March, two thousand twenty-five.
PRESENT: JOHN M. WALKER, JR., RICHARD C. WESLEY, JOSEPH F. BIANCO, Circuit Judges. _____________________________________
UNITED STATES OF AMERICA,
Appellee,
v. 23-7909-cr
ISAIAH SPAIN, AKA Q,
Defendant-Appellant. _____________________________________
FOR APPELLEE: Katherine A. Gregory, Assistant United States Attorney, for Michael DiGiacomo, Interim United States Attorney for the Western District of New York, Buffalo, New York.
FOR DEFENDANT-APPELLANT: Brendan White, White & White, New York, New York. Appeal from an amended judgment of the United States District Court for the Western
District of New York (Richard J. Arcara, Judge).
UPON DUE CONSIDERATION, IT IS HEREBY ORDERED, ADJUDGED, AND
DECREED that the amended judgment of the district court, entered on November 20, 2023, is
AFFIRMED.
Defendant-Appellant Isaiah Spain appeals from the district court’s amended judgment of
conviction following his guilty plea to a one-count superseding information, charging him with
conspiracy to possess with intent to distribute, and to distribute, ten grams or more of butyryl
fentanyl, heroin, fentanyl, and furanyl fentanyl, in violation of 21 U.S.C. §§ 846, 841(a)(1), and
841(b)(1)(B). The conviction arose from Spain’s participation, between 2016 and 2019, in a
conspiracy to distribute narcotics—including heroin, fentanyl, butyryl fentanyl, and furanyl
fentanyl—which resulted in a number of drug overdoses, two of which were fatal. On appeal,
Spain argues that his guilty plea must be vacated because, during his guilty plea proceeding, the
presiding magistrate judge failed to advise him of his right to appointed counsel, in violation of
Federal Rule of Criminal Procedure 11(b)(1)(D). 1 We assume the parties’ familiarity with the
underlying facts, procedural history, and issues on appeal, to which we refer only as necessary to
explain our decision to affirm.
On January 23, 2023, during Spain’s guilty plea proceeding, the magistrate judge asked
Spain a series of questions, pursuant to Rule 11, to determine whether the court should accept his
guilty plea, including whether Spain understood that he was “entitled to be represented at all stages
of this case[,] including the trial[,] by an attorney.” App’x at 96. It is uncontested that the
1 Pursuant to Rule 11(b)(1)(D), “the court must inform the defendant of, and determine that the defendant understands, . . . [his] right to be represented by counsel—and if necessary[,] have the court appoint counsel—at trial and at every other stage of the proceeding.” 2 magistrate judge did not inform Spain at this plea proceeding that he had a right to appointed
counsel if he could not afford to retain an attorney on his own. At the conclusion of the proceeding,
the magistrate judge found that Spain’s plea of guilty to the superseding information was knowing
and voluntary and recommended that the district court accept the plea. The district court
subsequently accepted the guilty plea and sentenced Spain principally to 250 months’
imprisonment, consistent with the terms of the plea agreement entered into by the parties pursuant
to Rule 11(c)(1)(C). This appeal followed.
We review a challenge to a conviction on the grounds that a district court allegedly failed
to comply with Rule 11 for plain error where, like here, the defendant did not raise an objection to
the district court. See United States v. Torrellas, 455 F.3d 96, 103 (2d Cir. 2006). To demonstrate
plain error, a defendant must establish that “(1) there is an error; (2) the error is clear or obvious,
rather than subject to reasonable dispute; (3) the error affected the [defendant]’s substantial rights;
and (4) the error seriously affects the fairness, integrity or public reputation of judicial
proceedings.” United States v. Balde, 943 F.3d 73, 96 (2d Cir. 2019). A Rule 11 violation affects
a defendant’s substantial rights where “there is ‘a reasonable probability that, but for the error, he
would not have entered the plea.’” United States v. Vaval, 404 F.3d 144, 151 (2d Cir. 2005)
(quoting United States v. Dominguez Benitez, 542 U.S. 74, 76 (2004)). In other words, a defendant
must demonstrate that “the district court’s error had an effect on his decision to plead guilty.”
United States v. Harrison, 241 F.3d 289, 293 (2d Cir. 2001). Moreover, “an appellate court
conducting plain-error review may consider the entire record—not just the record from the
particular proceeding where the error occurred.” Greer v. United States, 593 U.S. 503, 511 (2021).
Spain contends that, although the magistrate judge informed him of his right to counsel
during the guilty plea proceeding, the magistrate judge nevertheless plainly erred by not advising
3 him of his right to appointed counsel, in violation of Rule 11(b)(1)(D). More specifically, Spain
argues that the prolonged plea negotiation process, which took several years, and the seriousness
of the charges he faced indicated that there was a reasonable probability that he would have gone
to trial, but because neither he nor his family could continue to pay for retained counsel, he chose
to enter into the plea deal. Thus, Spain asserts that, had the magistrate judge reminded him of his
right to appointed counsel at the guilty plea proceeding, he would not have entered his guilty plea,
and instead would have gone to trial. We find these arguments unpersuasive.
As an initial matter, because the record indicates that, long before his guilty plea
proceeding, Spain was aware that he was entitled to counsel at all stages of his case and to
appointed counsel if he could not afford to hire an attorney, there is no reasonable probability that
the magistrate judge’s failure to remind him of that right at the guilty plea proceeding affected his
decision to plead guilty. In particular, at his initial appearance and arraignment on April 5, 2019,
in connection with the thirteen-count indictment filed against him, the magistrate judge advised
Spain that he had “the right to be represented at all stages of this case by an attorney,” and that he
had “the right to hire an attorney of [his] choice,” but if he could not afford to hire one, “the Court
[would] assign an attorney to represent [him], and the cost for that legal service [would] be paid
by the taxpayers of this country.” App’x at 27. The magistrate judge also determined that, after
reviewing Spain’s financial affidavit and engaging in a colloquy with him, Spain qualified for
court-appointed counsel and, as a result, appointed an assistant federal defender to represent Spain
in this case. The appointed assistant federal defender represented Spain from the date of the
arraignment until June 2019, when Spain’s retained counsel took over the representation. This
Court has previously found that, when facts similar to those at issue here are present, district courts
do not commit plain error during a guilty plea proceeding by not fully advising a defendant
4 regarding his right to counsel because in those cases the defendant’s prior knowledge of that right
undermined a contention that such an omission affected the defendant’s plea decision. See, e.g.,
United States v. Pattee, 820 F.3d 496, 505–06 (2d Cir. 2016) (finding no plain error for failing to
advise defendant during a guilty plea proceeding that the right to counsel applied at every stage of
the proceeding, where defendant was represented by retained counsel throughout the proceeding,
was informed of his right to counsel, including appointed counsel, at his arraignment, and had
completed a financial affidavit for purposes of assessing whether he qualified for appointed
counsel); see also United States v. Henderson, 827 F. App’x 105, 107 (2d Cir. 2020) (summary
order) (finding no plain error for failing to advise defendant of his right to appointed counsel during
a guilty plea proceeding where defendant previously was informed “a lawyer would be appointed
for him if he could not afford one” and defendant was represented by appointed counsel); United
States v. Vara-Davila, 410 F. App’x 395, 397 (2d Cir. 2011) (summary order) (finding no plain
error in failing to advise defendant, during his plea colloquy, that he would have the right to
assistance of counsel at every stage of the proceeding because the magistrate judge had advised
him of that right at a prior proceeding).
Moreover, even assuming arguendo Spain did not remember that the magistrate judge had
previously advised him of his right to appointed counsel at every stage of the case (and had
appointed counsel for him for several months), he still has not demonstrated that the magistrate
judge’s failure to remind him during the guilty plea proceeding that he was entitled to appointed
counsel affected his decision to plead guilty. See Harrison, 241 F.3d at 293. As for his contention
that the plea negotiation process and seriousness of the charges made it reasonably probable that
he would go to trial, that argument is undermined by the fact that Spain ultimately pleaded guilty
to a one-count superseding information for drug conspiracy, and by doing so, avoided the
5 possibility that he would be convicted at trial of the eighteen counts charged in the superseding
indictment filed in April 2022. As the district court noted during sentencing, had Spain been
convicted of those charges, which included more serious counts for a drug conspiracy that resulted
in serious bodily injury or death, he likely would have faced a more severe sentence than what he
agreed to in his Rule 11(c)(1)(C) plea, which had a range of 216 to 264 months’ imprisonment.
For example, if convicted of all counts in the superseding indictment, Spain faced not only a
mandatory minimum of 240 months’ imprisonment for causing the death of other individuals from
his distribution of narcotics, but also a substantially higher Sentencing Guidelines range. Thus,
his plea agreement both provided him with the possibility of receiving a sentence of less than 240
months and reduced his potential exposure to a significantly higher sentence based upon the
Guidelines.
Finally, we find Spain’s claim that he pleaded guilty because neither he nor his family could
afford trial counsel similarly unavailing. Spain argues that the fact that he has proceeded on appeal
with appointed counsel “strongly supports the conclusion” that the inability to afford a lawyer was
a “determining factor in the decision to accept a plea deal.” Appellant’s Br. at 27–28. However,
Spain retained counsel for the majority of this case, despite being qualified for, and in fact
previously receiving, appointed counsel, and he has identified no evidence in the record to indicate
that he could not have continued with retained counsel at trial, or to otherwise support his claim
that financial hardship caused him to take the guilty plea. These conclusory assertions, made only
in Spain’s appellate brief, are insufficient to demonstrate plain error. See Pattee, 820 F.3d at 505
(concluding that defendant had not established plain error where he offered no evidence in support
of his Rule 11 claim other than a “bare assertion that the errors in the plea allocution affected his
decision to plead guilty”).
6 In sum, we conclude that the magistrate judge did not commit plain error because Spain
failed to show that, if the magistrate judge had explicitly advised him during his guilty plea
proceeding that he was entitled to appointed counsel at every stage of the criminal proceeding,
“there is a reasonable probability that . . . he would not have entered the plea.” Vaval, 404 F.3d at
151 (internal quotation marks and citation omitted).
* * *
We have considered Spain’s remaining arguments and conclude that they are without merit.
Accordingly, the amended judgment of the district court is AFFIRMED.
FOR THE COURT: Catherine O’Hagan Wolfe, Clerk of Court