                              In the

    United States Court of Appeals
                 For the Seventh Circuit
                     ____________________
No. 18-2398
DAVID L. DAY, JR.,
                                             Petitioner-Appellant,
                                v.

UNITED STATES OF AMERICA,
                                             Respondent-Appellee.
                     ____________________

         Appeal from the United States District Court for the
         Southern District of Indiana, Indianapolis Division.
      No. 1:17-cv-00015-TWP-DLP — Tanya Walton Pratt, Judge.
                     ____________________

     ARGUED JANUARY 30, 2020 — DECIDED JUNE 24, 2020
                ____________________

   Before MANION, KANNE, and SYKES, Circuit Judges.
    SYKES, Circuit Judge. David Day, Jr., was indicted for con-
spiracy to commit wire fraud stemming from his participa-
tion in a fraudulent “credit repair” scheme operating in
Indianapolis. The government offered Day a favorable plea
deal that would have yielded a probable Guidelines sentenc-
ing range of 51 to 63 months in prison. Day’s federal defend-
er advised him to accept the deal. He was prepared to do so,
but his father urged him to consult a private lawyer—an
2                                                 No. 18-2398

acquaintance of his with no experience in criminal law. That
lawyer brought in an attorney experienced in federal crimi-
nal law, and the two told Day that he was not guilty of any
crime and should reject the government’s offer. Day accept-
ed that advice and hired the private lawyers for a hefty fee
raised by his family. The federal defender withdrew and
offered to make her case file available to new counsel.
    After the substitution of counsel, the government again
extended the same plea offer about six weeks before the trial
date. Though they hadn’t yet reviewed the case materials,
Day’s new private lawyers again advised him to reject it.
Day followed their advice and declined the deal. At the final
pretrial hearing a month later, Day again rejected the gov-
ernment’s plea offer on the record. Then, soon after the
hearing, the two lawyers met with Day and for the first time
told him he would lose at trial. Shocked, Day told them to
try to get the best deal they could. They instead advised him
to plead guilty and throw himself on the mercy of the court.
   Four days later, Day pleaded guilty without an agree-
ment. When the dust settled, he faced a sentencing range of
87 to 108 months. The district judge imposed a 92-month
prison sentence. Day filed a pro se motion for relief under
28 U.S.C. § 2255, arguing that his private attorneys were
constitutionally ineffective for advising him to reject the
favorable plea offer. The judge denied the motion without an
evidentiary hearing.
    That was error. The government now concedes the
deficient-performance element of Day’s Sixth Amendment
claim, and the facts set forth in his motion, if proven, could
establish prejudice. We vacate and remand for further
proceedings.
No. 18-2398                                                3

                       I. Background
A. Criminal Proceedings
    We draw the following account of the case from the court
record and Day’s § 2255 motion. Beginning in or around
2012, Day participated in a fraudulent scheme disguised as a
“credit repair service” for people with poor credit history.
As part of the scam, he sold misappropriated social-security
numbers to coconspirator “customers” with instructions on
how to use their new “credit profile number” to apply for
retail credit lines, which they then used to obtain larger
loans. Federal authorities eventually caught on, and in
September 2013 a grand jury returned a 34-count indictment
against Day and 17 coconspirators. Day faced one count of
conspiracy to commit wire fraud, 18 U.S.C. §§ 1343 and 1349,
and one count of making false statements in loan and credit
applications, id. § 1014. Federal defender Monica Foster was
appointed to represent him.
    In June 2014 the government offered Day a plea deal: if
he would plead guilty to the conspiracy count, the govern-
ment would move to dismiss the other count, stipulate to a
total offense level of 24, and recommend a sentence at the
low end of the Guidelines range. The agreement did not
specify a criminal-history category or Guidelines range. But
as the prosecutor later explained in a declaration, everyone
expected that with an offense level of 24 and Day’s criminal-
history category of I, the resulting Guidelines range would
be 51 to 63 months in prison. The agreement would be
submitted under Rule 11(c)(1)(B) of the Federal Rules of
Criminal Procedure and thus would not bind the court. As
Day recounts the plea negotiations, Foster told him that he
could “reasonably expect” the government to move for a
4                                                 No. 18-2398

departure based on his post-plea cooperation with authori-
ties, see U.S.S.G. § 5K1.1, which could reduce the bottom of
the Guidelines range to as low as 36 months.
    Foster advised Day to accept the offer because she be-
lieved that he had no viable defense. Day avers, however,
that Foster also told him that she thought the government
would accept a 40-month sentence under a binding plea
agreement pursuant to Rule 11(c)(1)(C). Day asked her to
approach the government with that proposal. But if the
government rejected Foster’s counteroffer, he was ready to
accept the government’s initial offer.
    Meanwhile, at his father’s urging, Day sought a second
opinion from private attorney John Schwartz, an acquaint-
ance of his father with no criminal-law experience. After
their first meeting, Schwartz said that he would “look into”
Day’s case. At a second meeting, Schwartz brought in John
Christ, a lawyer with experience in federal criminal law. Day
alleges that after he showed the attorneys some websites
offering similar “credit repair” services, they told him that
he was not guilty of any offense because he “could not be
convicted for conduct that others were engaging in openly.”
Without reviewing the case (and without disclosing that
they had not done so), Schwartz and Christ advised Day to
reject the plea deal and retain them for $30,000 to take the
case to trial. Day accepted that advice.
   Day’s father paid the $30,000 fee over the next several
months. Foster told Schwartz and Christ that the full case file
was available for pickup at her office. The file contained the
government’s discovery, including grand-jury transcripts
and transcripts of Day’s inculpatory interview with federal
agents. Schwartz and Christ filed their formal appearances
No. 18-2398                                                5

on December 12, 2014, and Foster then withdrew. Three days
later Schwartz and Christ moved to continue the trial, which
was scheduled to begin on January 26, 2015. They told the
court that Foster was still “in the process of forwarding the
discovery materials,” which they had “not yet received.”
The judge denied the motion.
    On December 17 the government sent the same plea offer
it had proposed in June. Day’s attorneys discussed the offer
with him “on or about” the third week of December and
were “dismissive” of it, assuring him that he could win at
trial because he had a “strong defense that what [he] had
been doing was lawful.” On the strength of that advice and
believing that his attorneys had reviewed the discovery
materials, Day turned down the government’s offer.
   The pretrial hearing was scheduled for early January. On
December 22 Day’s attorneys moved to postpone it, explain-
ing that they had “received extensive discovery materials
from the U.S. Attorney and the Federal Defender on …
December 19.” The judge granted the motion.
    The judge convened the rescheduled final pretrial hear-
ing on January 12. It did not go as Day had hoped. His
counsel arrived late and displayed a significant lack of
preparation for trial, which was less than two weeks away.
Day’s attorneys again sought a continuance to no avail. Even
so, Day formally rejected the government’s renewed plea
offer in open court.
    After the hearing Day’s attorneys met with him and for
the first time advised him that based on the strength of the
government’s evidence, he would lose at trial. Shocked at
this sudden change of advice, Day told his attorneys that he
6                                                           No. 18-2398

wanted to plead guilty and instructed them to get him “the
best deal they could negotiate.” Schwartz and Christ told
him that he would be better off pleading guilty without an
agreement and throwing himself on the mercy of the court.
   On January 16—four days after formally rejecting the
government’s renewed plea offer in open court—Day plead-
ed guilty to the conspiracy count without a plea agreement.
The government orally agreed to dismiss the remaining
count but made no other concessions or promises.
    The presentence report recommended that the court
adopt a total Guidelines offense level of 33, which included
greater enhancements than the government had agreed to in
the plea offer and also omitted a reduction for acceptance of
responsibility. 1 With Day’s criminal-history category of I, the
PSR recommended a sentencing range of 135–168 months. A
later addendum noted that the government had moved
under § 5K1.1 for a 2-level reduction based on Day’s cooper-
ation following his guilty plea.
   At sentencing the judge reduced the offense level by two
levels for acceptance of responsibility, see U.S.S.G. § 3E1.1,


1 The PSR and the proposed plea agreement both used a base offense
level of 7, U.S.S.G. § 2B1.1(a), and added a 2-level enhancement for the
unauthorized transfer or use of any means of identification (here, a
social-security number) to obtain any other means of identification (here,
a loan account), id. § 2B1.1(b)(11)(C)(i). But they differed on three other
enhancements. The PSR added 16 levels for loss amount, id.
§ 2B1.1(b)(1)(I), 4 levels for the number of victims, id. § 2B1.1(b)(2)(B),
and 4 levels for Day’s role in the offense, id. § 3B1.1(a). In contrast the
proposed plea agreement stipulated to a 14-level enhancement for loss
amount, 2 levels for the number of victims, and 2 levels for Day’s role in
the offense.
No. 18-2398                                                         7

but otherwise adopted the PSR’s recommendations with no
objection from defense counsel. By this time Christ had
withdrawn and only Schwartz represented Day. The adjust-
ed offense level was 31—seven levels higher than the gov-
ernment’s plea offer had contemplated—resulting in a final
Guidelines range of 108–135 months. The judge granted the
government’s § 5K1.1 motion, lowering the range to 87–
108 months. After considering the 18 U.S.C. § 3553(a) sen-
tencing factors, the judge imposed a term of 92 months in
prison.
    At some point after sentencing, Day spoke to Foster and
learned that Schwartz and Christ never picked up the case
file.
B. Motion to Vacate Sentence
    Proceeding pro se, Day filed a § 2255 motion to vacate his
sentence, asserting that Schwartz and Christ were constitu-
tionally ineffective for advising him to reject the govern-
ment’s plea offers despite never reviewing Foster’s case file
or the government’s discovery.2 Day’s motion characterized
the government’s initial plea offer as proposing a sentence of
“about 36 months” and the second as offering “about
54 months.” He alleged that if counsel had properly advised
him, he would have accepted either offer, which likely
would have resulted in a sentence much lower than
92 months.
   The government opposed the motion, explaining that a
plea offer of 36 months in prison was never on the table. The


2 Day also alleged that Schwartz and Christ were ineffective for three
other reasons not at issue here.
8                                               No. 18-2398

government also argued that Day could not establish that he
was prejudiced by his attorneys’ advice to reject the plea
deal that actually was offered—a recommended sentencing
range of 51 to 63 months—because nothing in the record
suggested that Day would have accepted it. And even if Day
could show that he would have accepted the deal, he could
not establish that he would have received less prison time
because the proffered plea agreement was not binding on
the judge. Finally, the government advised the court that it
had requested affidavits from Day’s private attorneys, but
Schwartz declined to provide one and Christ did not re-
spond.
    In his reply Day sought to clarify his statements about
the plea offers. He explained that he had described the
government’s first offer as he understood it at the time,
accounting for a possible reduction based on his post-plea
cooperation. In other words, the 36-month offer he described
was the government’s original 51–63 month offer, with the
possibility of credit for his cooperation as Foster had pre-
dicted; the December plea offer involved the same terms.
Day also submitted sworn declarations from himself and his
father to support his version of events and argued that the
government’s response showed that an evidentiary hearing
was necessary.
    The judge denied the § 2255 motion without a hearing,
explaining that Day had not made the required threshold
showing to warrant one. Apparently overlooking the clarifi-
cation in Day’s reply submission, the judge described his
allegations as referring to two separate plea offers: one
agreeing to a sentence “of about 36 months” and a second
offer of 54 months. That was inconsistent with the record,
No. 18-2398                                                          9

which established unequivocally that there was a single plea
offer presented on two occasions.
    Moving on to the elements of a Sixth Amendment claim
for ineffective assistance of counsel under Strickland v.
Washington, 466 U.S. 668 (1984), see Hill v. Lockhart, 474 U.S.
52, 58–59 (1985) (applying Strickland to plea bargaining), the
judge reasoned that the advice from Day’s attorneys did not
amount to deficient performance but was instead a reasona-
ble strategic decision. The judge also held that Day could not
establish prejudice because even if he had accepted the plea
offer, its terms were not binding on the court.
   Day appealed. We granted a certificate of appealability
and recruited pro bono counsel to assist him. 3
                           II. Discussion
    Day challenges the judge’s decision to deny his § 2255
motion without an evidentiary hearing. We review a deci-
sion to forgo an evidentiary hearing for an abuse of discre-
tion. Sawyer v. United States, 874 F.3d 276, 278 (7th Cir. 2017).
A hearing is required when “a petitioner alleges facts that, if
true, would entitle him to relief.” Torres-Chavez v. United
States, 828 F.3d 582, 586 (7th Cir. 2016) (quotation marks
omitted). But a judge may deny a hearing if the petitioner’s
allegations are “too vague and conclusory,” id., or if “the
files and records of the case conclusively show that the
prisoner is entitled to no relief,” 28 U.S.C. § 2255(b).




3 Attorney Caroline A. Flynn of Latham & Watkins LLP accepted
representation and has ably discharged her duties. We thank her for her
assistance to her client and the court.
10                                                No. 18-2398

    Day argues that he is entitled to an evidentiary hearing
because his allegations, if proven, establish both elements of
his Strickland claim: (1) his attorneys’ performance during
the plea-bargaining phase fell below an objective standard of
reasonableness and (2) their deficient performance caused
prejudice. See Lafler v. Cooper, 566 U.S. 156, 163 (2012). In
response, the government now concedes that Schwartz and
Christ performed deficiently when they advised Day to
reject the renewed plea offer. Still, the government argues
that no hearing is needed because Day cannot show preju-
dice.
    To prove Strickland prejudice in the plea-bargaining con-
text, the defendant must show a reasonable probability that
he would have accepted the government’s plea offer but for
the ineffective advice of his attorneys and that the court
would have accepted the agreement and imposed a less
severe sentence. Id. at 163–64. More specifically, Day must
prove two things: (1) it is reasonably probable that but for
the incompetent advice of his attorneys, he would have
accepted the government’s renewed plea offer and pleaded
guilty; and (2) it is reasonably probable that the judge would
have imposed a lower sentence. In the government’s view,
the existing record conclusively establishes Day cannot make
either showing.
    We see things differently. As a preliminary matter, the
judge’s decision to forgo an evidentiary hearing appears to
rest on a misreading of Day’s submissions. She construed his
§ 2255 motion as describing two distinct plea offers—one for
36 months and another for 54 months—when the record
clearly established that the government made a single offer
and renewed it after the substitution of counsel. The judge
No. 18-2398                                                11

apparently overlooked the clarification in Day’s reply brief.
In the end, everyone agreed that the government presented
the same offer twice, stipulating to an advisory Guidelines of
51 to 63 months.
    That misstep aside, the judge’s no-prejudice ruling rests
on a flawed legal analysis. The judge held that Day could not
show prejudice because the plea agreement would not bind
the court to a particular sentence. But the proper inquiry is
not whether the sentencing court is bound by a plea agree-
ment, but whether it is reasonably probable that the court
“would have accepted its terms,” and the resulting sentence
“would have been less severe” than the one that was actual-
ly imposed. Id. at 164; see also United States v. Carmichael,
216 F.3d 224, 227 (2d Cir. 2000) (remanding to consider
whether, if a prisoner had been advised to accept deal, the
court “would have imposed a sentence that differed from
the government’s recommendation”).
    The judge’s prejudice analysis also overlooks the practi-
cal realities of plea negotiations. Few court observers would
contend that the government’s views as reflected in its plea
stipulations and Guidelines recommendations have no
influence on a judge’s real-world sentencing decisions. See,
e.g., Shayna M. Sigman, An Analysis of Rule 11 Plea Bargain
Options, 66 U. CHI. L. REV. 1317, 1324 (1999) (“[J]udges
usually follow the nonbinding recommendation in [Rule 11]
type B agreements” in part because they know that “not
accept[ing] prosecutors’ sentenc[ing] recommendations …
will hamper … [plea negotiations] in future cases.”). Why
would prosecutors offer nonbinding plea agreements—and
defendants accept them—if they count for nothing in the
sentencing decision?
12                                                No. 18-2398

    Had the probation office been presented with the plea
agreement and its factual stipulations, it is reasonably
probable that the recommendations in the PSR would have
agreed with the government’s stipulations regarding the
applicable offense-level enhancements. See Justice Manual,
U.S. DEP’T OF JUSTICE, § 9-27.430 cmt. 2 (Feb. 2018),
https://www.justice.gov/jm/jm-9-27000-principles-federal-
prosecution#9-27.430 (noting that the DOJ policy on plea
agreements is to “only … stipulate to facts that accurately
reflect the defendant’s conduct”). But even if the probation
officer had not agreed, there’s a reasonable probability that
the judge would have accepted the parties’ stipulations over
the PSR’s recommendations based on the government’s
representations. If a PSR includes “facts that are inconsistent
with a stipulation in which a prosecutor has joined,” DOJ
policy obligates the prosecutor to “object to the report or add
a statement explaining the prosecutor’s understanding of the
facts or the reason for the stipulation.” Id.
    In a new argument raised for the first time on appeal, the
government argues that the judge properly denied Day’s
motion without a hearing because competent counsel—
Foster, his federal defender—previously advised him to
accept the plea deal, but he chose not to do so. In the gov-
ernment’s view, Foster’s sound advice bars a Strickland claim
based on the later ineffectiveness of substitute counsel. But
the Sixth Amendment right to the effective assistance of
counsel “extends to the plea-bargaining process,” not just to
discrete parts of it. Cooper, 566 U.S. at 162 (emphasis added);
see also Missouri v. Frye, 56 U.S. 134, 143 (2012) (noting that
the “plea-bargaining process is often in flux, with no clear
standards or timelines”).
No. 18-2398                                                  13

    Here, the government reoffered the plea deal as trial drew
near, giving Day the renewed option to accept it. He was
entitled to the effective assistance of counsel as he made his
decision. See Strickland, 466 U.S. at 690 (noting that courts
“must judge the reasonableness of counsel’s challenged
conduct … as of the time of counsel’s conduct”). Schwartz
and Christ advised Day to reject the renewed plea offer—
advice that the government now concedes was constitution-
ally deficient. That distinguishes Day’s situation from the
out-of-circuit cases the government cites in which multiple
attorneys gave conflicting advice at the same time about the
same plea offer. See, e.g., Clark v. Chappell, 936 F.3d 944, 969
(9th Cir. 2019) (concluding that the petitioner was not preju-
diced by one attorney’s advice to reject a plea deal because
another of his attorneys advised him to accept it); Logan v.
United States, 910 F.3d 864, 869–70 (6th Cir. 2018) (ruling that
the petitioner who received “both competent and deficient
advice on whether to accept the February 19 plea offer”
received effective assistance). Moreover, the record indicates
that Day planned to follow Foster’s advice and accept the
offer before he received the deficient advice from the other
attorneys.
   If Day was wrong to reject his first attorney’s advice re-
garding a plea, he may well have changed his mind if his
new attorneys had told him so. As Day’s argument suggests,
a defendant who seeks a second opinion and then learns that
the second lawyer agrees with the first lawyer is likelier to
accept a renewed plea offer than one who receives conflict-
ing advice. At the very least, an evidentiary hearing is
needed to test that proposition.
14                                                No. 18-2398

   The government warns that ruling in Day’s favor will
produce “absurd results” by “encourag[ing] defendants to
engage incompetent attorneys.” That strikes us as an entirely
unrealistic concern.
    The question of prejudice remains, and it requires further
factual development. The judge did not address whether it is
reasonably probable that Day would have accepted the
renewed plea offer had Schwartz and Christ advised him to
do so. The government contends that nothing in the record
supports Day’s allegation, but we disagree. Day’s father
submitted a declaration corroborating his son’s assertion
that he would have accepted the deal. See Sawyer, 874 F.3d at
279 (noting that “district courts may not discount a petition-
er’s declarations simply because they may be self-serving”
and relying on corroborating affidavits from family mem-
bers). Other aspects of the record support Day’s position,
including the fact that he pleaded guilty without an agree-
ment just days after rejecting the renewed plea offer and he
cooperated with the government thereafter. Cf. Frye, 566 U.S.
at 150 (“The Court of Appeals did not err in finding Frye’s
acceptance of the less favorable [open] plea offer indicated
that he would have accepted the earlier (and more favorable)
offer, had he been apprised of it … .”). Day has met his
“relatively light” burden to warrant an evidentiary hearing
on his claim. Torres-Chavez, 828 F.3d at 586.
   If on remand Day establishes a reasonable probability
that he would have accepted the renewed plea offer but for
the incompetent advice of his attorneys, his work is not yet
done. Day must still show a reasonable probability that he
would have received a sentence lower than 92 months. See
Frye, 566 U.S. at 148–49. If he does so, then the judge should
No. 18-2398                                               15

grant Day’s § 2255 motion and, within her discretion, craft
an appropriate remedy. See Cooper, 566 U.S. at 170–72
(providing guidance on remedies); Estremera v. United States,
724 F.3d 773, 779 (7th Cir. 2013) (noting that there may be
“permissible remed[ies]” beyond directing the prosecutor to
reoffer a rejected plea deal).
   Accordingly, we VACATE the judgment and REMAND for
an evidentiary hearing on whether Day was prejudiced by
the constitutionally deficient performance of his lawyers.
