In the
United States Court of Appeals
For the Seventh Circuit
No. 24-2913
DEREK FIELDS,
Petitioner-Appellant,
v.
UNITED STATES OF AMERICA,
Respondent-Appellee.
Appeal from the United States District Court for the
Northern District of Indiana, South Bend Division.
No. 3:21-cv-466 — Cristal C. Brisco, Judge.
ARGUED APRIL 16, 2026 — DECIDED AUGUST 17, 2026
Before HAMILTON, LEE, and TAIBLESON, Circuit Judges.
TAIBLESON, Circuit Judge. After rejecting multiple plea offers, Derek Fields was convicted by a federal jury of crimes arising from a violent kidnapping. He was ultimately sentenced to 43 years’ imprisonment. Now, Fields has moved for relief under 28 U.S.C. § 2255, arguing that his counsel was ineffective for failing to provide enough advice about a plea offer that, he claims, the Government extended to Fields during jury selection. According to Fields, he rejected that plea offer 2 No. 24-2913
because his trial counsel only informed him that it carried 37 years’ imprisonment, with no other details.
The district court denied Fields’s motion without an evidentiary hearing, and we affirm. Even assuming that the latebreaking plea offer existed and that Fields’s counsel provided deficient advice about it, Fields has not shown that he would have accepted it and received a lower sentence as a result. He therefore has not demonstrated the requisite prejudice to succeed on an ineffective-assistance-of-counsel claim. The district judge thus did not abuse her discretion in denying Fields’s motion without an evidentiary hearing.
I. Background
A.
In the early hours of September 8, 2015, Fields and his
codefendants kidnapped Adrian Harris, an acquaintance of Fields’s, at gunpoint. During the kidnapping, one defendant accidentally shot Harris in the arm. Over the course of about five hours, Fields and his codefendants restrained, gagged, and blindfolded Harris—all while beating him and demanding a ransom that was paid by his sister. Fearing that Harris would die, Fields and his codefendants ultimately dropped a blindfolded Harris in an alley; he was rescued soon after.1
The crime was not a whodunnit: Just two days after the
kidnapping, Fields was arrested pursuant to a federal criminal complaint charging him with kidnapping, making a ransom demand, and possessing a firearm as a felon. His two
1 Additional facts underlying Fields’s charges and conviction are detailed in our prior opinion, United States v. Brazier, 933 F.3d 796 (7th Cir. 2019).
No. 24-2913 3
codefendants were arrested around the same time. In October of 2015, a grand jury indicted Fields and his codefendants on the three charges in Fields’s criminal complaint, plus a charge of discharging a firearm during a crime of violence in violation of 18 U.S.C. § 924(c)(1)(A)(iii).
The Government extended multiple plea offers to Fields,
both before and after his indictment. Those offers each carried a mandatory minimum term of imprisonment under 18 U.S.C. § 924(c)—either a seven-year minimum for brandishing a firearm during a crime of violence, see § 924(c)(1)(A)(ii), or a tenyear minimum for discharging a firearm during a crime of violence, see § 924(c)(1)(A)(iii). Each plea offer also contemplated a substantial Guidelines imprisonment range.
Fields rejected these offers after consulting with his thenattorney, Fred Hains. We discuss those consultations in more detail below. Here, it suffices to note that according to Hains, Fields was “adamant” about rejecting plea offers that carried prison time over about 20 years, which Fields viewed as “a lifetime sentence.” That remained true across multiple meetings with Hains considering multiple plea offers, even though Fields and Hains also discussed “the fact that [Fields] was basically screwed” given the evidence against him.
Hains eventually withdrew as Fields’s counsel, and Fields cycled through new attorneys. He landed on attorney Philip Skodinski, who (unlike prior counsel) indulged Fields’s request to file a motion to suppress certain evidence. That motion was denied, and Fields proceeded to trial. After a threeday trial in November of 2016, a jury found Fields guilty on all charges. The district judge sentenced Fields to 636 months’ (53 years’) imprisonment.
4 No. 24-2913
Fields appealed, arguing for the first time that his conviction for discharging a firearm during a crime of violence under 18 U.S.C. § 924(c) was invalid because federal kidnapping is not a “crime of violence.” After oral argument, the Supreme Court decided United States v. Davis, 588 U.S. 445 (2019), which resolved the “crime of violence” question in Fields’s favor. So we vacated his § 924(c) conviction. United States v. Brazier, 933 F.3d 796, 800–02 (7th Cir. 2019). On remand, Fields was resentenced without the ten-year § 924(c)(1)(A)(iii) mandatory minimum, to 516 months’ (43 years’) imprisonment.
B.
After his conviction was final, Fields filed a motion under 28 U.S.C. § 2255. Under that provision, a federal prisoner may move to “vacate, set aside or correct [a] sentence” if it was “imposed in violation of the Constitution or laws of the United States.” 28 U.S.C. § 2255(a). Fields argued that his sentence had been tainted by ineffective assistance of counsel in violation of the Sixth Amendment—specifically, by Skodinski’s inadequate advice in connection with a plea offer.
In a declaration accompanying his § 2255 motion, Fields
alleged that during jury selection, Skodinski had passed him a plea agreement offered by the Government and instructed him to “just read it.” According to Fields, when he asked Skodinski “what it was,” Skodinski “told [him] it was a ‘37-year plea.’” Skodinski purportedly provided no other advice, and so Fields rejected the offer. In his § 2255 motion, Fields argued that “but for” Skodinski’s “deficient advice[,] there is a reasonable probability [that] Fields would have pleaded guilty and been sentenced to less jail time.” Fields did not, however, attach the plea agreement, nor did he describe any of its terms beyond it being a “37-year plea.”
No. 24-2913 5
In its opposition to Fields’s § 2255 motion, the Government recounted the extensive plea negotiations that took place while Hains represented Fields, relying in part on an affidavit from Hains that described these negotiations from the defense’s perspective. According to the Government, it did not extend any “further offers” to Fields’s subsequent counsel, including Skodinski. The Government also submitted an affidavit from Skodinski, who averred that he did not pass Fields a plea agreement during jury selection because the Government had not offered him one.
In reply, Fields attached another plea agreement—not the 37-year offer described in his original motion—that, he
claimed, Skodinski had also received at some point during his representation. The plea agreement attached to Fields’s reply brief would have required Fields to plead guilty to all four counts in the indictment with no sentence cap. Fields explained that he had attached this proposed plea agreement to “discredit[] the Government[’s]” argument that it had not extended any offers during Skodinski’s representation. But
Fields reiterated that his “§ 2255 motion raises a single, discrete claim of ineffective assistance of counsel” based on Skodinski’s failure “to adequately advise Fields regarding a proposed plea agreement presented at jury selection,” i.e., the 37-year plea offer.
In response, the Government confirmed that it had no record of either plea offer. Now focusing its arguments on the plea offer attached to Fields’s reply brief, the Government urged the district court to deny the § 2255 motion. The district court did so, denying Fields’s § 2255 motion without conducting an evidentiary hearing. Like the Government, the district judge’s analysis focused on the plea offer attached to Fields’s 6 No. 24-2913
reply brief. The district judge reasoned that Fields could not show that declining this plea offer prejudiced him, because his Sentencing Guidelines range would have been unchanged and he did not show that it was probable that he would have received a lower sentence if he had pleaded guilty.
Fields appealed, and we granted a certificate of appealability.
II. Discussion
Fields challenges the denial of his § 2255 motion without an evidentiary hearing. “When reviewing the denial of a federal prisoner’s § 2255 petition, we review the district court’s legal conclusions de novo, its factual findings for clear error, and its decision to forgo holding an evidentiary hearing for abuse of discretion.” Martin v. United States, 789 F.3d 703, 705 (7th Cir. 2015). An evidentiary hearing is “unnecessary” if “‘the files and records of the case conclusively show that the prisoner is entitled to no relief,’ or if the allegations are too vague and conclusory.” Torres-Chavez v. United States, 828 F.3d 582, 586 (7th Cir. 2016) (quoting 28 U.S.C. § 2255(b)).
Fields claims that his attorney’s inadequate advice about a plea offer violated his Sixth Amendment right to counsel. “It has long been recognized that the right to counsel is the right to the effective assistance of counsel.” McMann v. Richardson, 397 U.S. 759, 771 n.14 (1970). The Sixth Amendment right to counsel extends to the plea-bargaining context, such that “[i]f a plea bargain has been offered, a defendant has the right to effective assistance of counsel in considering whether to accept it.” Lafler v. Cooper, 566 U.S. 156, 168 (2012); see Missouri v. Frye, 566 U.S. 134, 140 (2012). To show ineffective assistance of counsel, Fields must demonstrate that his counsel’s
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performance was both deficient and prejudicial. Strickland v. Washington, 466 U.S. 668, 687 (1984).
As a threshold matter, we must clarify which alleged plea offer is at issue here. We agree with Fields that his claim is, and always has been, predicated on the 37-year plea that he claims to have received during jury selection. This is not a hard call; Fields’s filings below and before us are clear. We thus consider whether Fields may be entitled to relief on his claim that Skodinski insufficiently advised him about that 37-year plea offer.
In analyzing that claim, we will assume that Fields did, in fact, receive a plea offer during jury selection and that Skodinski advised him only that it was a “37-year plea.” And we will further assume—although it is far from clear, legally—that Skodinski’s failure to thoroughly review that offer was such deficient performance that it fell below the Sixth Amendment standard. See Frye, 566 U.S. at 149–50 (finding deficient performance prong met where counsel failed to communicate
plea offer at all before it lapsed); Overstreet v. Wilson, 686 F.3d 404, 406–07 (7th Cir. 2012) (“Frye does not consider whether counsel furnish ineffective assistance by failing to convey a plea offer ‘effectively’; we assume without deciding that
counsel must do so.”); Mitchell v. United States, 846 F.3d 937, 939–40 (7th Cir. 2017) (same).
Even with the benefit of those assumptions, Fields must
establish prejudice under Strickland. To do so, Fields must show that “(1) it is reasonably probable that but for the incompetent advice of his attorneys, he would have accepted the government’s [] plea offer and pleaded guilty; and (2) it is reasonably probable that the judge would have imposed a lower sentence.” Day v. United States, 962 F.3d 987, 992 (7th Cir. 8 No. 24-2913
2020); see also Frye, 566 U.S. at 148.
Fields cannot make either of those showings. First, the record is replete with contemporaneous evidence that, as his lawyer put it, Fields “had no inclination for a plea agreement.” Start with the preindictment plea offer that the Government first extended to Fields. In counseling Fields about that offer, Hains explained that Fields risked an additional three mandatory years of imprisonment if he declined the offer and the Government obtained an indictment to a more serious charge (discharging rather than brandishing a gun). Fields declined, explaining (as memorialized in Hains’s
notes), “what makes a difference whether it is 30 years or 33 years, or 37 years,” since any of those were “a life sentence.”
Fields rejected later plea offers based on similar reasoning. According to Hains, in considering a postindictment offer that Fields “underst[ood]” would provide “the best deal possible” at the time, Fields again declined, reasoning, “what’s the difference between twenty years and thirty years,” because “[i]n essence, it’s a lifetime sentence because his mother will be gone, his grandmother will be gone and his kids will be
grown.” Fields remained steadfast about rejecting any plea offers despite Hains’s repeated warnings about “the likely outcome of a trial.” “This consistent refusal to take a plea agreement is evidence that [Fields] did not suffer prejudice due to [his attorney’s] failure” to explain the 37-year offer. Foster v. United States, 735 F.3d 561, 567 (7th Cir. 2013).
Fields’s only evidence to the contrary is in a short declaration accompanying his § 2255 motion, which contains vague and internally contradictory statements. Fields asserts that Skodinski “never explained to me that I could enter an ‘open’ guilty plea to the indictment which would avoid trial and No. 24-2913 9
preserve my right to appeal the denial of my motion to suppress.” But that statement does not marry up with Fields’s legal claim, which is predicated on the 37-year plea offer. The 37-year plea offer was not an “open guilty plea,” which is a guilty plea “without the benefit of a plea agreement entered into with the Government.” United States v. Mansfield, 21 F.4th 946, 951 n.2 (7th Cir. 2021) (citation omitted); see also, e.g., United States v. Turner, 55 F.4th 1135, 1140 (7th Cir. 2022). Instead, Fields describes the 37-year offer as a written agreement, and a written agreement would have been necessary to impose any type of 37-year sentencing cap. Adding to the internal contradictions here, an “open guilty plea” generally would not have preserved Fields’s right to appeal the suppression issue; preserving that type of appeal requires a specific concession from the Government. See FED. R. CRIM. P. 11(a)(2); Turner, 55 F.4th at 1139–42. Nor does Fields anywhere suggest that the 37-year plea offer preserved his right to appeal the suppression issue, which was plainly important to him.
Beyond his confusing assertion about an open guilty plea, Fields generally claims that he “would have pled guilty” had Skodinski “gone over the advantages” of doing so. But it is undisputed that Fields knew the pros and cons of going to trial from Hains. Fields has not explained why Skodinski’s repetition of the same points would have made a difference, nor does he connect this broad allegation to the specific 37-year plea offer at issue here. As a result, Fields’s declaration does not rebut the undisputed and detailed record evidence that he would have refused any offer contemplating 37 years’ imprisonment.
Second, Fields also made no showing that, had he taken the 10 No. 24-2913
37-year plea offer, he would have received a lower sentence than the 516-month (43-year) sentence he is currently serving. While the Government may promise to limit its own sentencing recommendation in a plea agreement, the parties may not constrain a sentencing judge’s discretion without the judge’s approval. See FED. R. CRIM. P. 11(c). Fields has not alleged that the 37-year plea agreement would have bound his sentencing judge, nor that the judge would have accepted it if so. And the record points the other way: As the district judge considering his § 2255 motion observed, “the nature of Mr. Fields’[s] offense is alarming, and the Court’s view of his conduct would remain the same whether Mr. Fields went to trial or accepted a plea offer.”
Finally, it is also a problem for Fields that he successfully appealed his § 924(c) conviction and benefited from a ten-year sentencing reduction as a result. Had Fields pleaded guilty, he would not have been able to pursue that claim on appeal. See, e.g., Grzegorczyk v. United States, 997 F.3d 743, 747 (7th Cir. 2021) (“[Plaintiff]’s challenge to his § 924(c) conviction is the exact type of claim we [have] deemed waived by an unconditional guilty plea.”). Given that wrinkle, it is particularly difficult for Fields to explain how he would be better off today had he accepted the 37-year plea offer.
Thus even with a hefty thumb on the scale—assuming the
37-year plea offer existed, and that Skodinski’s advice about it was so scanty as to fall below the constitutional floor—the “files and records of the case” conclusively foreclose a finding of Strickland prejudice. Torres-Chavez, 828 F.3d at 586 (citation omitted). The district judge therefore did not abuse her discretion in denying Fields’s motion without an evidentiary hearing.
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***
The district court’s judgment is accordingly
AFFIRMED.