United States Court of Appeals For the First Circuit
No. 25-1079
UNITED STATES,
Appellee,
v.
JOAN ROSADO MALDONADO,
Defendant, Appellant.
APPEAL FROM THE UNITED STATES DISTRICT COURT FOR THE DISTRICT OF MASSACHUSETTS
[Hon. Margaret R. Guzman, U.S. District Judge]
Before
Barron, Chief Judge, Kayatta and Rikelman, Circuit Judges.
Sarah Varney, with whom Darren Griffis and Rudolf, Smith Griffis & Ruggieri, LLP were on brief, for appellant. Alexia R. De Vincentis, Assistant United States Attorney, with whom Leah B. Foley, United States Attorney, was on brief, for appellee.
July 6, 2026 BARRON, Chief Judge. Joan Rosado Maldonado
("Maldonado") pleaded guilty to one count of being a prohibited
person in possession of a firearm and ammunition, in violation of
18 U.S.C. § 922(g)(1), for which he was sentenced to a sixty-month
prison term, with credit for time served, and a thirty-six-month
term of supervised release. Finding merit to Maldonado's appeal,
we vacate his sentence and remand to the District Court.
I.
Because Maldonado pleaded guilty, "we draw the facts
from the plea colloquy, the unchallenged portions of the
presentence investigation report" ("PSR"), "and the sentencing
transcript." United States v. Santa-Soler, 985 F.3d 93, 95 (1st
Cir. 2021).
On September 10, 2021, two patrolling Worcester,
Massachusetts police officers drove past Maldonado standing
outside an apartment building. One of the officers noticed
Maldonado raise his arm into the air and, shortly thereafter, heard
a gunshot. Immediately, the two officers turned their patrol car
around and headed towards the building. Inside, they found
Maldonado standing outside the elevator bay. Upon searching him,
they found a loaded firearm tucked in his satchel.
On December 2, 2021, Maldonado was indicted for being a
prohibited person in possession of a firearm and ammunition, in
violation of 18 U.S.C. § 922(g)(1). On March 1, 2024, he pleaded
- 2 - guilty. As of that time, Maldonado had multiple prior convictions,
including, as relevant, (1) a 2010 conviction for trafficking in
cocaine, in violation of Mass. Gen. Laws ch. 94C, § 32E(b), and
(2) a 2019 conviction for possessing with intent to distribute a
Class B substance, in violation of Mass. Gen. Laws ch. 94C,
§ 32A(a).
Before sentencing, the United States Probation Office
prepared a PSR based on the United States Sentencing Guidelines
("Guidelines"). The PSR assigned Maldonado a criminal history
category of III and a total offense level of twenty-five. The PSR
calculated Maldonado's base offense level as twenty-four after
determining that he had "at least two [prior] felony convictions
of either a crime of violence or a controlled substance offense."
See U.S. Sent'g Guidelines Manual § 2K2.1(a)(2) (U.S. Sent'g
Comm'n 2024) [hereinafter "U.S.S.G."]. The PSR recommended a
sentencing range of seventy to eighty-seven months of
imprisonment.
Maldonado objected to the PSR. In pertinent part, he
argued that the base offense level was incorrectly calculated
because "[n]either of the potentially applicable
convictions -- for possession of a Class B substance . . . or
[t]rafficking [c]ocaine . . . -- qualify as 'controlled
substance[] offenses' under § 2K2.1." This was so, he continued,
because "Massachusetts law more broadly define[d] cocaine to
- 3 - include" [123I]ioflupane ("ioflupane"), which was not a scheduled
substance under federal law at the time of his federal sentencing.
Thus, he contended, his base offense level should have been twenty
and his resulting guideline range forty-six to fifty-seven months
of imprisonment.
On December 18, 2024, the District Court informed
Maldonado that it had overruled his objections. At a subsequent
virtual hearing on January 2, 2025, where it noted that it had not
yet made an oral or written ruling on those objections, the
District Court explained that it found "the term 'controlled
substance'" under Guideline § 2K2.1 to include "drugs that are
regulated by the federal Controlled Substances Act" ("CSA"), 21
U.S.C. §§ 801–904, as well as those "defined by state law." In
the end, it calculated his sentencing range under the Guidelines
to be seventy to eighty-seven months of imprisonment, followed by
up to three years of supervised release. It then sentenced him to
sixty months of imprisonment, followed by three years of supervised
release.
During the December hearing, the District Court also
discussed the various conditions that would accompany Maldonado's
term of supervised release. It recounted its imposition of a
"special condition[]" that Maldonado not "knowingly
communicate . . . with members . . . of any street gang." It
determined, however, the language of that condition "to be not as
- 4 - helpful as the articulation that" it then provided: Maldonado was
"not to associate with anyone who" he knew or should know was
"engaged in any criminal activity whatsoever."
In the written judgment that the District Court issued
following the hearing, however, it included both a "special
condition[]" proscribing Maldonado from "knowingly communicat[ing]
or otherwise interact[ing] with any members, affiliates, and/or
associates of any street gang including, but not limited to, the
Latin Kings" and a "standard condition[]" precluding him from
"communicat[ing] or interact[ing] with" anyone he knows is
"engaged in criminal activity."
Separately, at the December hearing, the District Court
instructed Maldonado that he was "to remain away from any
possession of a firearm. None." It continued by adding that
"anyone [he] kn[ew], who is in possession of a firearm, is someone
[he could not] be found with," regardless of whether they were a
"gang member" or whether they "legally possess[ed] a firearm."
At the subsequent January hearing, Maldonado objected to
this firearm-related condition. In objecting, he construed that
condition as "restricti[ng]" him from "having any association with
anyone who legally owns a firearm." The District Court overruled
this objection as well.
Nonetheless, the written judgment -- with respect to
this objection -- contained only the "standard condition[]" that
- 5 - Maldonado not "own, possess, or have access to a firearm,
ammunition, destructive device, or dangerous weapon." It
comparatively did not prohibit him from "be[ing] found with" anyone
he knew to be "in possession of a firearm."
Maldonado timely appealed.
II.
We review a District Court's interpretation of the
Guidelines de novo. United States v. Berroa, 856 F.3d 141, 162
(1st Cir. 2017).
III.
We begin and end with Maldonado's challenge to the
District Court's calculation of his sentencing range. At
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United States Court of Appeals For the First Circuit
No. 25-1079
UNITED STATES,
Appellee,
v.
JOAN ROSADO MALDONADO,
Defendant, Appellant.
APPEAL FROM THE UNITED STATES DISTRICT COURT FOR THE DISTRICT OF MASSACHUSETTS
[Hon. Margaret R. Guzman, U.S. District Judge]
Before
Barron, Chief Judge, Kayatta and Rikelman, Circuit Judges.
Sarah Varney, with whom Darren Griffis and Rudolf, Smith Griffis & Ruggieri, LLP were on brief, for appellant. Alexia R. De Vincentis, Assistant United States Attorney, with whom Leah B. Foley, United States Attorney, was on brief, for appellee.
July 6, 2026 BARRON, Chief Judge. Joan Rosado Maldonado
("Maldonado") pleaded guilty to one count of being a prohibited
person in possession of a firearm and ammunition, in violation of
18 U.S.C. § 922(g)(1), for which he was sentenced to a sixty-month
prison term, with credit for time served, and a thirty-six-month
term of supervised release. Finding merit to Maldonado's appeal,
we vacate his sentence and remand to the District Court.
I.
Because Maldonado pleaded guilty, "we draw the facts
from the plea colloquy, the unchallenged portions of the
presentence investigation report" ("PSR"), "and the sentencing
transcript." United States v. Santa-Soler, 985 F.3d 93, 95 (1st
Cir. 2021).
On September 10, 2021, two patrolling Worcester,
Massachusetts police officers drove past Maldonado standing
outside an apartment building. One of the officers noticed
Maldonado raise his arm into the air and, shortly thereafter, heard
a gunshot. Immediately, the two officers turned their patrol car
around and headed towards the building. Inside, they found
Maldonado standing outside the elevator bay. Upon searching him,
they found a loaded firearm tucked in his satchel.
On December 2, 2021, Maldonado was indicted for being a
prohibited person in possession of a firearm and ammunition, in
violation of 18 U.S.C. § 922(g)(1). On March 1, 2024, he pleaded
- 2 - guilty. As of that time, Maldonado had multiple prior convictions,
including, as relevant, (1) a 2010 conviction for trafficking in
cocaine, in violation of Mass. Gen. Laws ch. 94C, § 32E(b), and
(2) a 2019 conviction for possessing with intent to distribute a
Class B substance, in violation of Mass. Gen. Laws ch. 94C,
§ 32A(a).
Before sentencing, the United States Probation Office
prepared a PSR based on the United States Sentencing Guidelines
("Guidelines"). The PSR assigned Maldonado a criminal history
category of III and a total offense level of twenty-five. The PSR
calculated Maldonado's base offense level as twenty-four after
determining that he had "at least two [prior] felony convictions
of either a crime of violence or a controlled substance offense."
See U.S. Sent'g Guidelines Manual § 2K2.1(a)(2) (U.S. Sent'g
Comm'n 2024) [hereinafter "U.S.S.G."]. The PSR recommended a
sentencing range of seventy to eighty-seven months of
imprisonment.
Maldonado objected to the PSR. In pertinent part, he
argued that the base offense level was incorrectly calculated
because "[n]either of the potentially applicable
convictions -- for possession of a Class B substance . . . or
[t]rafficking [c]ocaine . . . -- qualify as 'controlled
substance[] offenses' under § 2K2.1." This was so, he continued,
because "Massachusetts law more broadly define[d] cocaine to
- 3 - include" [123I]ioflupane ("ioflupane"), which was not a scheduled
substance under federal law at the time of his federal sentencing.
Thus, he contended, his base offense level should have been twenty
and his resulting guideline range forty-six to fifty-seven months
of imprisonment.
On December 18, 2024, the District Court informed
Maldonado that it had overruled his objections. At a subsequent
virtual hearing on January 2, 2025, where it noted that it had not
yet made an oral or written ruling on those objections, the
District Court explained that it found "the term 'controlled
substance'" under Guideline § 2K2.1 to include "drugs that are
regulated by the federal Controlled Substances Act" ("CSA"), 21
U.S.C. §§ 801–904, as well as those "defined by state law." In
the end, it calculated his sentencing range under the Guidelines
to be seventy to eighty-seven months of imprisonment, followed by
up to three years of supervised release. It then sentenced him to
sixty months of imprisonment, followed by three years of supervised
release.
During the December hearing, the District Court also
discussed the various conditions that would accompany Maldonado's
term of supervised release. It recounted its imposition of a
"special condition[]" that Maldonado not "knowingly
communicate . . . with members . . . of any street gang." It
determined, however, the language of that condition "to be not as
- 4 - helpful as the articulation that" it then provided: Maldonado was
"not to associate with anyone who" he knew or should know was
"engaged in any criminal activity whatsoever."
In the written judgment that the District Court issued
following the hearing, however, it included both a "special
condition[]" proscribing Maldonado from "knowingly communicat[ing]
or otherwise interact[ing] with any members, affiliates, and/or
associates of any street gang including, but not limited to, the
Latin Kings" and a "standard condition[]" precluding him from
"communicat[ing] or interact[ing] with" anyone he knows is
"engaged in criminal activity."
Separately, at the December hearing, the District Court
instructed Maldonado that he was "to remain away from any
possession of a firearm. None." It continued by adding that
"anyone [he] kn[ew], who is in possession of a firearm, is someone
[he could not] be found with," regardless of whether they were a
"gang member" or whether they "legally possess[ed] a firearm."
At the subsequent January hearing, Maldonado objected to
this firearm-related condition. In objecting, he construed that
condition as "restricti[ng]" him from "having any association with
anyone who legally owns a firearm." The District Court overruled
this objection as well.
Nonetheless, the written judgment -- with respect to
this objection -- contained only the "standard condition[]" that
- 5 - Maldonado not "own, possess, or have access to a firearm,
ammunition, destructive device, or dangerous weapon." It
comparatively did not prohibit him from "be[ing] found with" anyone
he knew to be "in possession of a firearm."
Maldonado timely appealed.
II.
We review a District Court's interpretation of the
Guidelines de novo. United States v. Berroa, 856 F.3d 141, 162
(1st Cir. 2017).
III.
We begin and end with Maldonado's challenge to the
District Court's calculation of his sentencing range. At
sentencing, the District Court determined that Maldonado's base
offense level was twenty-four pursuant to Guideline § 2K2.1(a)(2).
That Guideline directs a District Court to apply a base offense
level of twenty-four "if the defendant committed any part of the
instant offense subsequent to sustaining at least two felony
convictions of . . . a controlled substance offense." U.S.S.G
§ 2K2.1(a)(2). A "controlled substance offense," in turn, is so
defined:
[A]n offense under federal or state law, punishable by imprisonment for a term exceeding one year, that --
(1) prohibits the manufacture, import, export, distribution, or dispensing of a controlled substance (or a counterfeit
- 6 - substance) or the possession of a controlled substance (or a counterfeit substance) with intent to manufacture, import, export, distribute, or dispense; or
(2) is an offense described in 46 U.S.C. § 70503(a) or § 70506(b).
Id. § 4B1.2(b); see id. § 2K2.1 cmt. n.1 ("'Controlled substance
offense' has the meaning given that term in § 4B1.2(b) . . . .").
Maldonado argues that the District Court erred in
applying a base offense level of twenty-four because his prior
convictions did not qualify as convictions of a "controlled
substance offense" for purposes of the Guidelines. In so arguing,
he states that "the District Court improperly relied upon [his]
two prior Massachusetts 'cocaine' convictions as the predicates
for application of [§ 2K2.1(a)(2)]." These cocaine convictions
are, as mentioned previously, (1) a 2010 conviction for
trafficking in cocaine, in violation of Mass. Gen. Laws ch. 94C,
§ 32E(b), and (2) a 2019 conviction for possessing with intent to
distribute a Class B substance, in violation of Mass. Gen. Laws
ch. 94C, § 32A(a).1
1Below, Maldonado's objection to the application of § 2K2.1(a)(2) was based on these two convictions as well. The government, however, also referenced Maldonado's 2010 conviction for conspiring to violate drug laws, in violation of Mass. Gen. Laws ch. 94C, § 40. The District Court, finding that the two convictions to which Maldonado referred were valid predicates, did not resolve whether, under its theory, the 2010 conspiracy conviction would also qualify as a conviction of a "controlled substance offense." Neither party, on appeal, argues that this conviction affects our analysis.
- 7 - Maldonado argues as follows. He contends that the
definition of "controlled substance offense" incorporated in
Guideline § 2K2.1(a)(2) encompasses "only those substances
regulated by the . . . CSA." At all relevant times, however,
Massachusetts has scheduled ioflupane -- a substance derived from
cocaine via ecgonine -- as a Class B drug, see Mass. Gen. Laws
ch. 94C, § 31(Class B)(a)(4), whereas the federal government has
not scheduled ioflupane as a controlled substance since 2015, see
21 C.F.R. § 1308.12(b)(4)(ii) (Sept. 11, 2015); Schedules of
Controlled Substances: Removal of [123I]Ioflupane From Schedule II
of the Controlled Substances Act, 80 Fed. Reg. 54715, 54717
(Sept. 11, 2015). Therefore, Maldanado argues, "[b]ecause the
Massachusetts definition of 'cocaine' is broader than its federal
counterpart" -- i.e., "the statutes are not a categorical
match" -- his "prior convictions are not convictions for a
'controlled substance offense,' as defined by" Guideline
§ 4B1.2(b).2
2Guideline § 2K2.1(a)(2) requires that a defendant have two prior controlled substance offense convictions for the enhancement to apply. Here, one of these convictions is asserted to be Maldonado's 2010 conviction for trafficking in cocaine. Neither party argues that the timing of that conviction matters in this case. Nevertheless, given our holding in United States v. Fulcar, we note that the timing that matters is the time of his federal sentencing. No. 25-1524, slip op. at 32 (1st Cir. July 6, 2026) (applying the time-of-federal-sentencing approach).
- 8 - The government, for its part, argues that the term
"'controlled substance' within the definition of 'controlled
substance offense'" in Guideline § 4B1.2(b) "refers to a substance
regulated by either federal or state law." Thus, because there is
no dispute that, under Massachusetts law, ioflupane was
"controlled" at all relevant times, the government contends that
it constitutes a "controlled substance," such that his
Massachusetts law convictions constitute convictions of a
controlled substance offense, as defined by Guideline § 4B1.2(b).
We agree with Maldonado's interpretation. For the
reasons set forth in United States v. Fulcar, No. 25-1524, slip
op. at 33-45 (1st Cir. July 6, 2026), we find that the term
"controlled substance" encompasses only substances regulated by
the CSA. Therefore, because the Massachusetts definition of
"cocaine" was not a categorical match to the CSA at the time of
Maldonado's federal sentencing,3 his two pertinent state
convictions do not qualify as convictions of a "controlled
substance offense," as defined by Guideline § 4B1.2(b). We
therefore must vacate and remand his prison sentence, as there is
no suggestion that the District Court "'inevitably' would have
imposed the same sentence" absent this procedural error. United
3 The government does not contest that the categorical approach applies. See United States v. Crocco, 15 F.4th 20, 21 (1st Cir. 2021) (applying the categorical approach where "neither" party "points to the modified approach").
- 9 - States v. Rosa-Borges, 174 F.4th 281, 290 (1st Cir. 2026) (quoting
United States v. Diaz, 285 F.3d 92, 98 (1st Cir. 2002)). Indeed,
it made clear that it could not "say what [it] would have done if
the PSR was different." See id. ("If we are not convinced that
the error was harmless, we must vacate and remand.").4
IV.
For the foregoing reasons, we vacate Maldonado's
sentence and remand the case for resentencing consistent with this
opinion.
4 Maldonado's briefing on appeal also attacks two of his supervised release conditions -- one of which the government concedes was imposed in error -- based, in part, on the daylight between the oral and written sentencing pronouncements. See supra Part I. But, because we are vacating his sentence, we need not reach the questions that his challenges to the supervised release conditions occasion. After all, insofar as the conditions were ambiguous, we anticipate that the District Court will clear up any muddied waters in its imposition of a new sentence.
- 10 -