Coleman v. United States

79 F.4th 822

Frederick J. COLEMAN, Petitioner-Appellant, v. UNITED STATES of America, Respondent-Appellee.

No. 22-1678

United States Court of Appeals, Seventh Circuit

Argued February 15, 2023

Decided August 15, 2023

Appeal from the United States District Court for the Central District of Illinois. No. 4:17-cv-4270 — Sara Darrow, Chief Judge.

Linda T. Coberly, Katherine Stallings Bailey, Attorneys, Winston & Strawn LLP, Chicago, IL, for Petitioner-Appellant.

W. Scott Simpson, Attorney, Office of the United States Attorney, Springfield, IL, for Respondent-Appellee.

Before Easterbrook, Wood, and Lee, Circuit Judges.

Lee, Circuit Judge.

In 2014, Frederick Coleman was sentenced to life imprisonment for conspiring to distribute crack cocaine. The district judge based the sentence on 21 U.S.C. § 841(b)(1)(A), which, at the time, mandated a life sentence for a defendant who previously had committed two or more felony drug offenses. After we denied his direct appeal, Coleman filed a pro se motion under 28 U.S.C. § 2255 to vacate his sentence, arguing that his defense counsel had provided ineffective assistance by not informing him of the potential life sentence. Later, he filed a motion to amend his pleading, expanding on his allegations, but, by that time, the limitations period had run. After ruling against Coleman on his original claim, the district court denied the motion to amend, finding that the amendment did not "relate back" to his initial pleading. Because the district court abused its discretion in reaching that conclusion, we reverse and remand for further proceedings as to Coleman's amended ineffective assistance of counsel claim.

I. BACKGROUND

In 2013, Coleman was convicted of conspiring to distribute crack cocaine. See 21 U.S.C. §§ 841(a)(1), (b)(1)(A), 846. Pursuant to the Controlled Substances Act in effect at that time, Coleman was sentenced to the statutorily mandated term of life imprisonment based on having at least two prior convictions for a "felony drug offense." Id. § 841(b)(1)(A) (2012).¹ We affirmed his sentence on direct appeal. United States v. Brown, 822 F.3d 966, 976 (7th Cir. 2016).

Coleman then filed a timely pro se motion to vacate his sentence pursuant to 28 U.S.C. § 2255. Coleman's § 2255 motion asserted, among other things, that his appointed counsel, Anthony Vaupel, was ineffective for having failed to inform him of the government's pretrial 21 U.S.C. § 851 Notice of Enhancement. This notice informed Coleman that, should he be found guilty at trial, the government would seek to enhance his sentence to life imprisonment based on his prior Illinois cocaine-related convictions, which, it believed, qualified as "felony drug offenses" under 21 U.S.C. § 841(b)(1)(A). According to Coleman, had Vaupel shown him this notice, he never would have agreed to go to trial.

To inquire into these allegations, the district court first entered an order that Coleman had waived the attorney-client privilege as to his communications with Vaupel regarding "the government filing a section 851 notice and [Coleman]'s potential life sentence." It also ordered Vaupel to submit an affidavit addressing Coleman's claim.

In his affidavit, Vaupel stated that he had informed Coleman on more than one occasion that he faced, and would receive, a mandatory life sentence if found guilty. Vaupel also attested that he had told Coleman that the mandatory life sentence was due to his prior convictions, and that despite the government's willingness to enter a proffer agreement with Coleman, it was unwilling to waive the § 851 enhancement.

Before the district court ruled on Coleman's § 2255 motion, Coleman moved, again pro se, to amend it pursuant to Federal Rule of Civil Procedure 15(c). His amendment contained more detailed allegations and argued specifically that Vaupel was ineffective by failing to object to the § 851 notice on the grounds that, under the categorical approach espoused in Taylor v. United States, 495 U.S. 575, 110 S.Ct. 2143, 109 L.Ed.2d 607 (1990), Coleman's prior Illinois cocaine convictions did not qualify as "felony drug offenses" under § 841(b)(1)(A) given that Illinois defined "cocaine" more broadly than federal law.

The district court denied Coleman's initial § 2255 motion, as well as his motion to amend. Without reaching the merits of the amended claim, the court determined that Coleman's motion to amend did not relate back to his initial pleading because "the claims rest[ed] on distinct types of attorney misfeasance and [we]re supported by different facts." Coleman v. United States, No. 4:17-cv-04270-SLD-JEH, 2022 WL 673702, at *8 (C.D. Ill. Mar. 7, 2022). And because Coleman's motion to amend was filed more than a year after his conviction became final, the district court found it untimely. Id. at *9; see 28 U.S.C. § 2255(f)(1) (providing a one-year statute of limitations for collateral review). Then, finding that reasonable jurists may disagree on this point, the district court granted Coleman a certificate of appealability on his claim.² Id. Coleman appealed, and we recruited counsel.³

II. DISCUSSION

Section 2255 provides a federal prisoner with the means to collaterally attack the propriety of his sentence. Relief under this statute is an "extraordinary remedy," and therefore only available in limited circumstances. Almonacid v. United States, 476 F.3d 518, 521 (7th Cir. 2007). One such circumstance is where defense counsel's representation is so ineffective that it violates the defendant's Sixth Amendment rights. U.S. Const. amend. VI; Strickland v. Washington, 466 U.S. 668, 686, 104 S.Ct. 2052, 80 L.Ed.2d 674 (1984). Coleman argues that his appointed counsel was constitutionally ineffective by failing to object to the § 851 notice. As he sees it, his attorney should have argued that Coleman's prior convictions did not qualify as "felony drug offenses" that could be used to enhance his sentence to life imprisonment under § 841. See generally United States v. Ruth, 966 F.3d 642 (7th Cir. 2020).⁴

Before we can reach the merits of Coleman's ineffective assistance of counsel claim, however, we must resolve two preliminary questions. First, we must determine whether appellate review of a district court's disposition of a pleading amendment under the "relation-back" provision of Federal Rule of Civil Procedure 15(c) is de novo or for an abuse of discretion. We must then apply that standard to determine the propriety of the district court's conclusion that Coleman's amendment did not relate back to the filing of his original motion.

A. Standard of Review

When a party seeks to amend its pleading, district courts "should freely give leave when justice so requires." Fed. R. Civ. P. 15(a)(2). "The Supreme Court has interpreted this rule to require a district court to allow amendment unless there is a good reason—futility, undue delay, undue prejudice, or bad faith—for denying leave to amend." Life Plans, Inc. v. Sec. Life of Denver Ins. Co., 800 F.3d 343, 357-58 (7th Cir. 2015) (citing Foman v. Davis, 371 U.S. 178, 182, 83 S.Ct. 227, 9 L.Ed.2d 222 (1962)). This "liberal standard," id. at 357, is limited, however, by any applicable statute of limitations. See Mayle v. Felix, 545 U.S. 644, 655, 125 S.Ct. 2562, 162 L.Ed.2d 582 (2005).

Where a party seeks to amend a pleading after the statute of limitations has run, he must turn to the relation-back provision of Rule 15(c), which allows such amendment if it "asserts a claim or defense that arose out of the conduct, transaction, or occurrence set out—or attempted to be set out—in the original pleading." Fed. R. Civ. P. 15(c)(1)(B).

It is well-settled that review of a district court's disposition of a motion to amend under Rule 15(a) is for an abuse of discretion.⁵ See, e.g., Foman, 371 U.S. at 182, 83 S.Ct. 227 ("Of course, the grant or denial of an opportunity to amend [under Rule 15(a)] is within the discretion of the District Court[.]"); Runnion ex rel. Runnion v. Girl Scouts of Greater Chi. & Nw. Ind., 786 F.3d 510, 524 (7th Cir. 2015) (applying deferential review but noting that, where a district court's denial is futility-based, our review "includes de novo review of the legal basis for the futility"). But we have been less clear on the appropriate standard of review when a district court decides whether a proposed amendment "relates back" to a pleading under Rule 15(c). Indeed, over six years ago, we made a mental note to "clarify the correct standard in a future case when the matter is properly before the court." Mulvania v. Sheriff of Rock Island Cnty., No. 16-1711, 2017 WL 2726577, at *2 (7th Cir. May 16, 2017) (denying petition for rehearing en banc). Compare Arreola v. Godinez, 546 F.3d 788, 796 (7th Cir. 2008) (applying abuse of discretion review), O'Brien v. Ind. Dep't of Corr. ex rel. Turner, 495 F.3d 505, 507 (7th Cir. 2007) (same), and Bibbs v. Sheriff of Cook Cnty., 618 F. App'x 847, 851 (7th Cir. 2015) (same), with Delgado-Brunet v. Clark, 93 F.3d 339, 342 (7th Cir. 1996) (applying de novo review).⁶ With this issue squarely before us, we make clear that a district court's disposition of a motion to amend a pleading that turns on the "relation-back" provision of Rule 15(c) is reviewed for an abuse of discretion.

As an initial matter, the fact that this issue comes to us via a § 2255 proceeding is of no consequence. Habeas corpus cases under § 2255 are civil cases generally governed by the Federal Rules of Civil Procedure. Conley v. United States, 5 F.4th 781, 794 (7th Cir. 2021) (citing Banister v. Davis, — U.S. —, 140 S. Ct. 1698, 1705, 207 L.Ed.2d 58 (2020)); see Beason v. Marske, 926 F.3d 932, 938 (7th Cir. 2019) (discussing application of Rule 15's relation-back provision to a § 2255 motion); Fed. R. Civ. P. 81(a)(4). See generally Mayle, 545 U.S. at 655, 125 S.Ct. 2562 (applying Rule 15(c) to § 2244 habeas corpus proceedings). Accordingly, our holding today applies generally to the relation-back provision of Rule 15(c); it is not limited...