In the

    United States Court of Appeals
                 For the Seventh Circuit
                     ____________________
No. 19-1676
UNITED STATES OF AMERICA,
                                                 Plaintiff-Appellee,
                                 v.

ALEX GUERRERO,
                                             Defendant-Appellant.
                     ____________________

          Appeal from the United States District Court for the
           Northern District of Indiana, Hammond Division.
 No. 2:10-cr-00109-TLS-APR-22 — Theresa L. Springmann, Chief Judge.
                     ____________________

   ARGUED NOVEMBER 5, 2019 — DECIDED JANUARY 7, 2020
               ____________________

   Before FLAUM, ROVNER, and HAMILTON, Circuit Judges.
    HAMILTON, Circuit Judge. Since 2015, defendant-appellant
Alex Guerrero has sought a reduction of his prison sentence
under Amendment 782 to the United States Sentencing
Guidelines, which reduced guideline ranges for drug quanti-
ties. Despite some procedural complications, we agree with
Guerrero that he is entitled to and has not yet received one
opportunity for full consideration of the merits of his request.
Accordingly, we vacate the decision of the district court and
2                                                  No. 19-1676

remand so that he may properly present such a motion, the
merits of which are for the sound discretion of the district
court.
I. Factual and Procedural Background
    Guerrero was a Chicago police officer who also partici-
pated in drug trafficking by the Latin Kings gang in Chicago
and northwestern Indiana. In 2013, he pleaded guilty to four
counts: (1) conspiring to participate in racketeering activity,
in violation of 18 U.S.C. § 1962(d); (2) conspiring to possess
with intent to distribute five kilograms or more of cocaine and
1000 kilograms or more of marijuana, in violation of 21 U.S.C.
§ 846; (3) interfering with commerce by threats or violence, in
violation of 18 U.S.C. § 1951; and (4) using and carrying a fire-
arm during and in relation to crimes of violence and drug traf-
ficking, in violation of 18 U.S.C. § 924(c)(1)(A). Even with a
criminal history category of I, Guerrero’s original sentencing
guideline range for the first three counts was life in prison,
based on a total offense level of 43. The guideline recommen-
dation for the fourth count was 60 months to be served con-
secutively to the sentence for the other counts, as required by
statute.
    Guerrero did not receive life plus 60 months, though. He
provided substantial assistance to the government in prose-
cuting a number of his Latin Kings co-conspirators. As a re-
sult, Guerrero and the government came to a plea agreement
pursuant to Federal Rule of Criminal Procedure 11(c)(1)(B),
under which the parties would recommend that he serve a to-
tal of 228 months in prison: 168 months (rather than life) on
the first three counts, plus 60 months on the fourth. The dis-
trict court (Judge Lozano) was not bound by the recommen-
dation, but he accepted it and sentenced accordingly.
No. 19-1676                                                    3

   The court’s explanation of the sentence played a role in
some of the later confusion. The court did not say it was
simply imposing a below-guideline sentence under 18 U.S.C.
§ 3553(a) and (e). Nor did the court say that it was just grant-
ing a downward departure under U.S.S.G. § 5K1.1 for sub-
stantial assistance. Instead, the court said it was imposing a
downward departure of six offense levels pursuant to the
government’s motion for a downward departure under
§ 5K1.1, plus a further reduction of another two levels for un-
specified “other factors.” In conjunction with Guerrero’s
other reductions and enhancements, the eight-level departure
pointed to a hypothetical guideline range of 168 to 210 months
on the first three counts.
    Amendment 782 to the United States Sentencing Guide-
lines, which became effective on November 1, 2014, reduced
by two levels the offense levels for most drug-trafficking
crimes. The Sentencing Commission made Amendment 782
retroactive under U.S.S.G. § 1B1.10. Guerrero sought to bene-
fit from this amendment. On July 20, 2015, he sent a letter to
the district court requesting that he be appointed counsel in
order to file a fully developed motion for resentencing under
the amendment. The district court rejected Guerrero’s request
on August 13, 2015, saying that our decision in United States v.
Foster required this result. 

, 888 (7th Cir. 2013)
(“[P]risoners who seek lower sentences following retroactive
changes to the Guidelines do not receive counsel at public ex-
pense.”). This was not a correct reading. Foster holds that dis-
trict courts are not required to appoint counsel under these cir-
cumstances, but it does not prohibit them from doing so.
    In what no doubt seemed at the time like a helpful step,
the court set the stage for this appeal by proceeding on its own
4                                                    No. 19-1676

initiative to consider Guerrero’s eligibility for a sentence re-
duction under Amendment 782, citing 18 U.S.C. § 3582(c)(2).
In its order of October 27, 2015, the district court denied relief
under Amendment 782. Judge Lozano found that Guerrero
was eligible for a two-level reduction under Amendment 782
but that the two-level reduction would make no difference to
his ultimate prison sentence:
       As a result of Amendment 782, Guerrero’s total
       offense level for Counts 1, 2 and 14 is reduced to
       41, for a guideline range on these counts of 324–
       405 months. Under Amendment 782, the Court
       may deduct the six (6) levels previously reduced
       due to the Government’s motion for a reduc-
       tion, but cannot also deduct the two levels re-
       ceived previously for other factors. See U.S.S.G.
       section 1B1.10(b)(2) (explaining that generally,
       the Court cannot reduce a sentence below the
       minimum of the amended guideline range, but
       allowing for an exception where the original
       sentence was below the guideline range due to
       substantial assistance). If the six (6) levels were
       deducted, his sentencing range would be 168–
       210 for Counts 1, 2 and 14—the same range in
       which he was originally sentenced. As a result,
       in the specific circumstances of this case, Guer-
       rero cannot benefit from Amendment 782.
In other words, the two levels credited at Guerrero’s 2013 sen-
tencing for “other factors”—which, in our reading of the rec-
ord, appear to be just part of the total downward departure
he received primarily for substantial assistance under his plea
agreement—were held essentially to cancel out the reduction
No. 19-1676                                                      5

under Amendment 782. In March 2016, Guerrero filed a mo-
tion for clarification. The court construed that as a late motion
to reconsider and denied it. Guerrero sought to appeal this
denial to our court, but that appeal was dismissed after he
failed to secure leave to file in forma pauperis.
    In 2018, Guerrero tried again, leading to this appeal. With
the aid of counsel this time, he sought a sentence reduction
under Amendment 782 pursuant to 18 U.S.C. § 3582(c)(2), this
time adding reliance on the Supreme Court’s decision in
Hughes v. United States, 

(2018). In Hughes, the
Court held that relief under § 3582(c)(2) should be available to
defendants with binding plea agreements under Federal Rule
of Criminal Procedure 11(c)(1)(C), “to permit the district court
to reconsider a prior sentence to the extent the prisoner’s
Guidelines range was a relevant part of the framework the
judge used to accept the agreement or determine the sen-
tence.” At 1778. Because his sentence was based on the Guide-
lines, Guerrero argued, Hughes made him eligible for relief
under Amendment 782.
    The district court (Chief Judge Springmann, to whom the
case was reassigned after Judge Lozano’s death) denied this
motion for two reasons. First, the court reasoned, Hughes has
no bearing on Guerrero because his plea had been subject to
Rule 11(c)(1)(B). It was therefore not a binding plea agreement
covered by Hughes. Second, the court held that Guerrero’s
motion, essentially again seeking a sentence reduction under
Amendment 782, was barred as an impermissible successive
motion under § 3582(c)(2), as we interpreted it in United States
v. Beard, 

, 292 (7th Cir. 2014), quoting United States
v. Redd, 

, 651 (7th Cir. 2011). The district court thus
6                                                 No. 19-1676

did not consider the merits of Guerrero’s arguments for relief
under Amendment 782. Guerrero then filed this appeal.
    We have jurisdiction under 18 U.S.C. § 3742(a). We review
denials of § 3582(c)(2) motions for abuse of discretion. United
States v. Hall, 

, 875 (7th Cir. 2010). “We may find
an abuse of discretion, though, where a district court ‘based
its ruling on an erroneous view of the law.’” United States v.
Sainz, 

, 604 (7th Cir. 2016), quoting Cooter & Gell
v. Hartmarx Corp., 

, 405 (1990). We agree with the
district court that Hughes does not apply to this case, but we
conclude that, as a matter of law, the 2015 proceedings should
not be counted against Guerrero as his one chance to seek re-
lief under Amendment 782. We therefore hold that the denial
of Guerrero’s counseled motion in 2018 was an error.
II. Recharacterizing Guerrero’s 2015 Letter
    We begin with the 2015 letter that sent Guerrero’s attempt
at resentencing into a procedural death spiral. His letter read
in full:
       Dear Madame or Sir,
       I am asking the court to appoint legal counsel
       for me. I am specifically requesting that my ap-
       pointed counsel petition the Court and ask that
       I be re-sentenced under the drug minus 2
       amendment. If there is anything else that you
       require me to send to you please let me know.
       Very Truly Yours,
       /s/ Alex Guerrero
On its own initiative, the district court recharacterized this
short and simple letter—which clearly requested only the
No. 19-1676                                                                 7

appointment of counsel and did not make or develop any le-
gal arguments—as a motion for resentencing under
§ 3582(c)(2). That was improper.1
    It is “exceptional” within our adversarial system for a
court to recharacterize a party’s request, especially when do-
ing so may harm that party’s interests. Castro v. United States,

, 385–86 (2003) (Scalia, J., concurring). A retroac-
tive guideline amendment and § 3582(c)(2) pose such a risk
because a prisoner is allowed only one bite at this particular
apple. In Castro, the Supreme Court considered a similar
problem: whether and when courts may recharacterize the fil-
ings of pro se prisoners as motions seeking habeas corpus re-
lief under 28 U.S.C. § 2255, which also restricts second or suc-
cessive motions. Castro held that district courts may not re-
characterize a pro se litigant’s motion as a first § 2255 motion
without first “notify[ing] the pro se litigant that it intends to
recharacterize the pleading, warn[ing] the litigant that this

    1 In its brief, the government construed Guerrero’s pleading of Octo-
ber 13, 2015 as a tacit admission that his July 2015 letter was a § 3582(c)(2)
motion. That uncounseled filing, entitled “Request of Status,” read in full:
“NOW COMES, petitioner Alex Guerrero, proceeding pro se in the above
captioned cause Humbly Request the Status of petitioners 3582(c)(2),
‘Drug Minus Two’ motion filed with Honorable Court on or about July
2015.” Guerrero filed this pleading two months after Judge Lozano indi-
cated his intent to proceed to consider the merits of Guerrero’s request for
resentencing. We are not surprised that a pro se prisoner litigant described
his case in the same terms the district judge himself used. Given the power
of a district court under the circumstances, people in Guerrero’s position
are more likely to hope for the best on the merits rather than challenge
mistaken procedural classifications that they almost certainly do not un-
derstand or appreciate. In keeping with the rest of our reasoning based on
Castro v. United States here, it would not be just to hold Guerrero’s misla-
beling against him.
8                                                   No. 19-1676

recharacterization means that any subsequent § 2255 motion
will be subject to the restrictions on ‘second or successive’ mo-
tions, and provid[ing] the litigant an opportunity to withdraw
the motion or to amend 

(majority opinion).
    Such a warning is needed because the pro se litigant may
otherwise lose her or his only opportunity to make the legal
argument upon which freedom depends—an unfair result, to
say the least. Given the one-motion-per-amendment limit that
we have found implicit in § 3582(c)(2), the district court’s re-
characterization of Guerrero’s letter as his one permitted mo-
tion raises essentially the same problems of fairness that Cas-
tro addressed under § 2255. We believe the logic of Castro re-
quires the same warnings for a prisoner whose filing is being
recharacterized as a motion for relief under § 3582(c)(2), and
those warnings were not provided here.
    Castro also provides guidance on a further procedural
wrinkle here, which is that Guerrero tried to challenge the
2015 denial of his recharacterized motion, first with a late mo-
tion to reconsider and then with an appeal that our court dis-
missed when Guerrero failed to obtain leave to proceed in
forma pauperis or to pay the docketing fee. In Castro, the gov-
ernment argued that Castro’s failure to appeal the original re-
characterization of his filing meant the recharacterization was
valid and could no longer be challenged as the “law of the

–84. The Supreme Court rejected the ar-
gument, reasoning that the prisoner’s failure to challenge the
recharacterization was, without the needed warnings, the re-
sult of his inability to make an informed judgment about the
actions of the district court: “Indeed, an unwarned pro se liti-
gant’s failure to appeal a recharacterization simply under-
scores the practical importance of providing the warning.
No. 19-1676                                                       9

Hence, an unwarned recharacterization cannot count as a
§ 2255 motion for purposes of the ‘second or successive’ pro-
vision, whether the unwarned pro se litigant does, or does not, take
an appeal.” 

(emphasis added). Similarly, here Guer-
rero’s unwarned failure to challenge the district court’s re-
characterization in either the district court or in his attempt to
appeal the original denial does not foreclose his counseled
2018 motion under § 3582(c)(2).
    Like Castro, when Guerrero was proceeding without
counsel in 2015, he found himself trapped by procedural rules
that he did not anticipate in his letter. The brevity and content
of the letter show that he intended first to request counsel, and
only later, with the benefit of counsel, to develop and present
his best legal arguments in favor of resentencing under
Amendment 782. The letter did not even gesture toward any
particular argument that might be made. Thus, when the
court proceeded to the merits of a § 3582(c)(2) motion on its
own initiative, it did so without the adversarial briefing that
would have illuminated the issues. Perhaps in part because of
this procedural decision, the district court’s analysis of the ap-
plicability of Amendment 782 to Guerrero’s sentence was
wrong on the merits, as discussed next. And, as interpreted
by the district court in 2019, Guerrero thereby lost his only
opportunity to make his arguments, with approximately 60
months of his sentence in the balance.
   On the merits, Judge Lozano miscalculated in 2015 how
Amendment 782 would apply to Guerrero’s guideline range.
We must walk through the before-and-after in some detail.
Our discussion applies only to the guideline range for the first
three counts to which Guerrero pleaded; a consecutive 60
10                                                   No. 19-1676

months for the fourth count would be added to any sentence
he received on the first three.
   In his original sentencing in 2013, Guerrero’s total offense
level was 43 (base offense level of 38, plus eight levels for
other guideline enhancements, minus three levels for ac-
ceptance of responsibility). At his sentencing hearing, the
court sentenced him as if his offense level had been reduced
by eight levels for his substantial assistance (six levels as rec-
ommended by the government in support of its motion, and
two more for unspecified reasons at the discretion of the
court), resulting in a 168-month sentence.
    In proceeding on his own to the merits of Guerrero’s case
under Amendment 782 in 2015, Judge Lozano assumed Guer-
rero should receive a two-level reduction under Amendment
782, which would seem to have reduced his base offense level
to 36 and his total offense level to 41. The judge held constant
the eight-level increase for other enhancements and the three-
level decrease for acceptance of responsibility. The source of
the confusion involved the treatment of the original down-
ward departure. The judge said that Guerrero received only a
six-level downward departure for substantial assistance, ra-
ther than the total of eight levels. Although the brief discus-
sion is not transparent, the judge seems to have read U.S.S.G.
§ 1B1.10(b)(2) as allowing a new sentence to reflect the six lev-
els of downward departure based on substantial assistance,
but not the two additional levels that were part of the original
departure.
    That was mistaken as a legal matter. Under U.S.S.G.
§ 1B1.10(b)(1), courts considering relief under § 3582(c)(2)
“shall substitute only the amendments listed in subsection (d)
for the corresponding provisions that were applied when the
No. 19-1676                                                   11

defendant was sentenced and shall leave all other guideline
application decisions unaffected.” More specifically, depar-
tures for substantial assistance are addressed in
§ 1B1.10(b)(2)(B): “a reduction comparably less than the
amended guideline range determined under [§ 1B1.10(b)(1)]
may be appropriate.” This provision leaves the district judge
considerable flexibility, to say the least. It certainly does not
prohibit reductions based on retroactive amendments in sub-
stantial assistance cases. See generally Dillon v. United States,

(2010) (recognizing limits to § 3582(c)(2) relief).
    Dillon requires that all guideline calculations from the
original sentencing that were not affected by the retroactive
amendment remain in place because § 3582(c)(2) is “a narrow
exception to the rule of finality” of criminal sentences under
Federal Rule of Criminal Procedure 35. 

The discre-
tion that Dillon affords to district courts is quite specific:
framed by the § 3553(a) factors, the district court may decide
that a sentence reduction under the amendment at issue in the
prisoner’s § 3582(c)(2) motion is not warranted. However, the
district court may not reevaluate decisions made at the time
of the original sentencing to apply other, unrelated guideline
adjustments.
     The departure used to set Guerrero’s 2013 sentence was
expressed in terms of guideline offense levels, which is appar-
ently the standard practice in the Northern District of Indiana.
It is clear from the record that the eight-level departure rec-
ommended by both sides was intended to achieve a well-be-
low-guideline sentence based on Guerrero’s substantial assis-
tance to the government. Under § 1B1.10(b)(2)(B), the district
court may use Amendment 782 to impose a new sentence that
is “comparably” below the guideline range as amended by
12                                                    No. 19-1676

Amendment 782. In other words, nothing in § 3582(c)(2),
Amendment 782, or § 1B1.10 prohibited the district court
from resentencing Guerrero to a term on his non-firearm
counts that would be roughly two offense levels below his
original sentence. We express no view on whether he should
receive such a reduction; that is a matter for the district court’s
sound discretion on remand.
III. Denial of Guerrero’s 2018 Motion as Successive
    The government argues, however, that it is too late for
Guerrero to win relief from the district court’s errors in han-
dling his 2015 letter. Following the reasoning in Castro, we dis-
agree.
    The district court was correct that our decisions in Beard
and Redd prohibit prisoners from more than “one bite at the
apple per retroactive amendment to the sentencing guide-
lines.” 

. “Once the district judge makes a
decision, Rule 35 applies and curtails any further power of re-
vision, unless the Commission again changes the Guidelines
and makes that change, too, retroactive.” 

.
For the reasons explained above, however, we conclude that
Guerrero’s 2015 letter did not constitute a first motion under
§ 3582(c)(2), so that the district court erred by holding that his
2018 filing was a prohibited successive motion. Our decision
here does not affect the holdings of Beard and Redd; they
simply do not apply where the district court took it upon itself
to recharacterize a quite different submission by a prisoner as
his one and only opportunity to seek relief under Amendment
782, and did so without warning him and giving him a chance
to renounce the proposed recharacterization, per the logic of
Castro.
No. 19-1676                                                   13

    We agree with Chief Judge Springmann that Hughes does
not apply to Guerrero’s sentence. Hughes clearly limited its
holding only to binding pleas under Rule 11(c)(1)(C), address-
ing whether (c)(1)(C) pleas are, for purposes of § 3582(c)(2),
“based on” a guideline sentencing range and thus subject to
revision under retroactive guideline amendments. See

(“The controlling issue here is
whether a defendant may seek relief under § 3582(c)(2) if he
entered a plea agreement specifying a particular sentence un-
der Federal Rule of Criminal Procedure 11(c)(1)(C).”). This
subject had been confused since the Court’s splintered deci-
sion in Freeman v. United States, 

(2011). Guerrero’s
plea deal was a nonbinding agreement under Rule 11(c)(1)(B).
For purposes of § 3582(c)(2), it was based on the Guidelines
from the beginning. He has always been legally eligible for
relief under § 3582(c)(2) for any retroactive amendments that
would affect his original guideline calculation.
   To sum up, Guerrero has not yet had the one bite at the
Amendment 782 apple to which he is entitled under
§ 3582(c)(2). Now, with the assistance of counsel, he should be
able to marshal his best arguments so that the district court
can benefit from full presentation of the issues. The denial of
Guerrero’s 2018 motion under § 3582(c)(2) is VACATED and
the case is REMANDED for proceedings consistent with this
opinion.