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 conspiracy to commit wire fraud stemming from his participation in a fraudulent “credit repair” scheme operating in 

Indianapolis. The government offered Day a favorable plea 

deal that would have yielded a probable Guidelines sentencing range of 51 to 63 months in prison. Day’s federal defender 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 criminal law, and the two told Day that he was not guilty of any 

crime and should reject the government’s offer. Day accepted 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 government’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 agreement. 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 government 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 criminalhistory 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 authorities, 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 believed 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 acquaintance 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, explaining 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 hearing 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 pleaded 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 cooperation 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 adjusted offense level was 31—seven levels higher than the government’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) sentencing 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 constitutionally ineffective for advising him to reject the government’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 respond.

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 predicted; 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 clarification 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 reasonable 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 decision to forgo an evidentiary hearing for an abuse of discretion. 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 prejudice.

To prove Strickland prejudice in the plea-bargaining context, 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 agreement, 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 actually 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 practical 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-federalprosecution#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 government’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 constitutionally 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 prejudiced 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 regarding 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 conflicting 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 petitioner’s declarations simply because they may be self-serving” 

and relying on corroborating affidavits from family members). Other aspects of the record support Day’s position, 

including the fact that he pleaded guilty without an agreement 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.