### In the 

# United States Court of Appeals For the Seventh Circuit

____________________ No. 18

- 2398
D AVID L. D AY , J R

. , P etitioner

- Appellant ,

v.
U NITED S TATES OF A M ERICA , Respondent

- Appellee

.

____________________ Appeal from the United States District Court for the Southern Distric t of I ndiana , Indianapolis Division

. No. 1:17

- cv

- 00015

- TWP

- DLP

— Tanya Walton P r att , Judge

.

____________________
A RGUED J ANUARY 30, 2020

— D ECIDED J UNE 24 , 2020

____________________

Before M ANION , K ANNE , and S YKES , Circuit Judges

. S YKES , Circuit Judge

. David Day, Jr. , was indicted for conspirac y 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 u rged him to consult a private lawyer

— an2 No. 18

- 2398

acquaintance of his with no experience in criminal law . Thatlawyer 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 governmen t’s offer

. Day accepted that advice and hired the private lawyers for a hefty fee raised by his family. T he federal defender withdrew and offered to make her case file available to new counsel.
After th e 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 p lead 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 distri ct judge imposed a 92

- month prison sentence . Day filed a pro se mo tion for relief under 28 U.S.C. § 2255 , argu ing that his private attorneys were constitutionally ineffective for advising him to reject the favorable plea offer . The judge denied the motion without an evidentiary hearin g. 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

. W e vacate and remand for further proceedings

.No. 1 8

- 2 398 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 fraud ulent 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 lin es, which they then used to obtain large r 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 off ered 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 G uidelines range. The agreement did not

s pecify a criminal

- history category or G uidelines range . B ut 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 G uidelines range would be 51 to 63 mo nths in prison . T he 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 Da y re count s the plea negotiations, Foster told him that he could “reasonably expect” the government to move for a4 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 G uidelines range to as low as 36 months. Foster advised Day to accept the offer because she believed that he had no viable defense. Day a vers, however, that Foster also told him that sh e 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 . B ut 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 fat her 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 th ey 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 Ch rist 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 appearancesNo. 1 8

- 2 398 5

on December 12, 2014, and Foster then withdrew. Three days later Schwartz and Christ moved to continu e the tria l, which

was scheduled to begin on January 26, 2015 . They told the
court that Foster was still “in the process of forwar ding the discovery materials,” which they had “not yet received.” The judge denied the motion.
On December 1 7 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 Dece mber 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 th at advice and believing that his attorneys had review ed the discovery materials , Day turned down the government’s offer

. The p retrial hearing was scheduled for early January. O n 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 prepara tion 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 t ime advised him that based on the strength of the government’s evidence, he would lose at trial

. Shocked at th is sudden change of advice, Day told his attorneys that he6 No. 18

- 2398

w anted to plead guilty and instructed them to get him “the best deal they could negotia te.” 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.
O n 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 Guide lines offense level of 33 , which included greater enhancements than the government had agreed to in the p lea offer and also omitted a reduction for acceptance of responsibility. 1 With Day’s criminal

- history category of I, the PSR recommended a se ntencing r ange 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 offen se level by two levels for acceptance of respo nsibility , s ee 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. 1 8

- 2 398 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 G uidelines rang e 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, t he judg e imposed a term of 92 months in prison. At some point after sentenc ing , Day spoke to Foster and learned that Schwartz and Christ never picked up the case file.

B. Motion to Vacate Sentence

P roceeding pro se, Day filed a § 2255 motion to vacate his sentence, a sserting 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 i f counsel had properly advised him, he would have accepted either offer , which likely would have resulted in a sente nce 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

. T he

2 Da y 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

— b ecause nothing in the record

s uggest ed that Day would have accepted it . And even if Day could show that he would have accepted the deal , he co uld
not establish that he would have received less prison time because the proffered plea agreement w as n ot bind ing on the judge

. Finally, t he government advised the court that it had requested affidavits from Day’s private attorneys, but Schwartz declined to prov ide one and Christ did not respond

. In his reply Day sought to clarify his statements about the plea offer s. 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 p ost

- 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 sub mitted 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 ne cessary

. The judge denied the § 2255 motion without a hearing , explain ing that Day had not ma d e the required threshold showing to warrant one

. Apparently overlooking the clarification in Day’s reply submission, the judge describe d 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. 1 8

- 2 398 9

which established unequivocally that there was a single plea offer presented on two occasions. Moving on to t he elements of a Sixth Amendment claim f or ineffective assistance of coun sel under Strickland v. Washington , 466 U.S. 668 (1984) , s ee 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 inste ad a r easonable 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 c ourt

. Day appeal ed . W e 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 § 2255motion without an evidentiary hearing. We review a decision to forgo a n 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) (quot ation 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 e ntitled 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 cli ent and the court.10 No. 18

- 2398

Day argues that he is entitled to a n 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, t he government now concedes that Schwartz and Christ performed deficiently when they advised Day to reject the renewed plea offer. Still, th e 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 s pecifically, Day must prove two things: (1) it is reasonabl y 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 t he judge would have imposed a l ower sentence

. In the government’s view, the existing record conclusively establishes Day cannot m ake either showing. We see things differently. As a preliminary matter , t he judge’s decision to forgo a n evidentiary hearing appears to
rest on a misreading o f Day’s submis sions

. 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

. T h e judg eNo. 1 8

- 2 398 11

apparently overlook ed the clarification in Day’s reply brief

. I n the end, everyone agreed that the g overnment presented the same offer twice , stipulating to an advisory Guidelines of 51 to 63 months

. T hat mis step aside , the judge ’s no

- prejudice ruling rests on a flawed legal analysis

. The judge held that D ay 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 pl ea 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”).

T he judge’s prejudice analysis also overlooks the practical realities of plea negotiations . Few court observers would contend that the government’s view s as reflected in its plea stipulations and G uidelines recommendations ha ve no influence on a judge ’ s real

- world sentencing decisions

. S ee, e.g. , Shayna M. Sigman, An Analysis of Rule 11 Plea Bargain Options , 66 U. C HI

. L. R EV

. 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] prosecuto rs’ 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

H ad 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 enhanceme nts. See Justice Manual , U.S. D EP ’ T OF J USTICE , § 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 ref lect the defendant’s conduct”). But even if the probation officer had not agreed , the re’s a reasonable probability that the judge would have accepted the parties’ stipulations over the PSR ’s recommendations based on the government’s representations . I f a P SR 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, t he government argues that the judge properly denied Day’s motion without a hearing because competent counsel

— Foster , his federal def ender

— 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
t he Sixth Amendment right to the effectiv e 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, wit h no clear standards or timelines”).No. 1 8

- 2 398 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 69 0 (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 t he
out

- of

- circuit cases the government cite s in which multiple attorneys gave conflicting advice at the same time about the

same plea offer. S ee, 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 86 4, 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 advi ce 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 sug gests, a defendant who seeks a second opinion and then learns that the second lawyer agrees with the first lawyer is likelier toaccept a renewed plea offer than one who receives conflicting advice. At the very least, an evidentiary hearing is needed to te st that proposition.14 No. 18

- 2398

T he government warns that ruling in Day’s favor w ill produce “ absurd results” by “encourag[ing] defendants to engage incompetent attorneys.” That s trikes us as an entirely

un realistic concern.
Th e question of prejudice re mains, and it requires further factual development. T he 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 re cord 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 declarat ions simply because they may be self

- serving”and relying on corroborating affidavits from family members). O ther aspects of the record support Day’s position, including the fact that he pleaded guilty without an agreement just days after rejecting the ren ewed 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 esta blishes a reasonable probability that he would have accepted the renewed plea offer but for the incompetent advice of his attorneys , h is 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 shouldNo. 1 8

- 2 398 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 V ACATE the ju dgment and R EMAND for an evidentiary hearing on whether Day was prejudiced by the constitutionally deficient performance of his lawyers

.