In the

United States Court of Appeals

For the Seventh Circuit ____________________

No. 17-1439

JESUS ARREOLA-CASTILLO,

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. 14-cv-2118 — Larry J. McKinney, Judge.

____________________

ARGUED APRIL 10, 2018 — DECIDED MAY 3, 2018

____________________

Before WOOD, Chief Judge, and FLAUM and KANNE, Circuit 

Judges.

FLAUM, Circuit Judge. Petitioner Jesus Arreola-Castillo was 

convicted of a federal drug crime. Because he had at least two 

prior felony drug convictions in New Mexico, he was subject 

to the recidivism provisions of 21 U.S.C. § 841. Pursuant to 

that statute, he received a mandatory minimum sentence of 

life in prison. He subsequently challenged the underlying felony drug convictions in New Mexico state court, which the 
2 No. 17-1439

state court ultimately vacated. Now, he moves to reopen his 

federal sentence under 28 U.S.C. § 2255, arguing that he is no 

longer subject to the recidivism enhancement because the 

prior state convictions have been vacated. The district court 

denied his § 2255 petition on the ground that it was timebarred. It relied on 21 U.S.C. § 851(e), which prohibits an individual from challenging the validity of a prior conviction

that is more than five years old at the time the government 

seeks the recidivism enhancement. Because Arreola-Castillo 

is not challenging the validity of his prior convictions, but rather their very existence, we reverse. 

I. Background

In 2006, a jury found Arreola-Castillo guilty of conspiracy 

to distribute 1,000 kilograms or more of marijuana in violation 

of 21 U.S.C. §§ 841(a)(1) and 846. The government filed two 

informations under 21 U.S.C. § 851 alleging that Arreola-Castillo had previously been convicted of two felony drug offenses in New Mexico in 1996. Because he had two or more 

prior felony drug convictions, the district court was required 

to impose a mandatory life sentence under the recidivism provisions of 21 U.S.C. § 841(b)(1)(A). Had it not been for the 

mandatory life sentence, Arreola-Castillo’s Guidelines sentencing range would have been 188–235 months in prison. We 

affirmed Arreola-Castillo’s sentence on direct appeal in 2008. 

See United States v. Arreola-Castillo, 539 F.3d 700 (7th Cir. 2008).

Arreola-Castillo subsequently challenged both underlying 

state convictions in New Mexico state courts. He moved to 

withdraw the guilty pleas in those convictions on the ground 

that he received ineffective assistance of counsel. Specifically, 

Arreola-Castillo claimed that his attorney did not inquire into 
No. 17-1439 3

his immigration status or sufficiently advise him of the immigration consequences of pleading guilty. The New Mexico 

state courts agreed and accordingly vacated the convictions 

on November 19, 2014 and June 29, 2015. 

In December 2014, after his first conviction was vacated, 

Arreola-Castillo moved to reopen his federal sentence under 

§ 2255. The government initially moved to dismiss the petition as an unauthorized second or successive petition under 

28 U.S.C. §§ 2244 and 2255(h). The court denied that motion, 

ruling that Arreola-Castillo’s petition was based on a claim 

that did not become ripe until his state convictions were vacated. 

Next, the government argued that Arreola-Castillo’s claim 

was “meritless” in light of 21 U.S.C. § 851(e). That provision 

bars an individual from “challeng[ing] the validity of any 

prior conviction alleged under this section which occurred 

more than five years before the date of the information alleging such prior conviction.” 21 U.S.C. § 851(e). The government argued that § 851(e) precludes Arreola-Castillo’s claim 

because the informations alleging the prior convictions were 

filed in 2006—more than five years after his (now vacated) 

convictions occurred in 1996. In response, Arreola-Castillo argued that § 851(e), which assumes the existence of a prior conviction and addresses its validity, does not apply because his 

convictions have been vacated. 

In January 2017, the district court held that § 851(e) bars 

Arreola-Castillo’s claims, and accordingly denied his petition 

for relief under § 2255. We subsequently granted Arreola-Castillo’s request for a certificate of appealability. Although the 

parties had not addressed the issue below, we instructed them 
4 No. 17-1439

to brief the timeliness of Arreola-Castillo’s claim under 

§ 2255(f)(4). 

II. Discussion

“On an appeal from the denial of a § 2255 motion, we review the district court’s legal conclusions de novo and its factual findings for clear error.” Keller v. United States, 657 F.3d 

675, 679 (7th Cir. 2011). “A § 2255 motion must be granted 

when a defendant’s ‘sentence was imposed in violation of the 

Constitution or laws of the United States.’” Fountain v. United 

States, 211 F.3d 429, 433 (7th Cir. 2000) (quoting 28 U.S.C. 

§ 2255)). 

A. We Decline to Address the Government’s Forfeited 

Timeliness Argument Under § 2255(f)(4)

There is a one-year statute of limitations for filing habeas 

petitions. 28 U.S.C. § 2255(f). In relevant part, the limitation 

period runs from “the date on which the facts supporting the 

claim or claims presented could have been discovered 

through the exercise of due diligence.” Id. § 2255(f)(4). In Johnson v. United States, the Supreme Court held that vacatur of a 

prior state conviction used to enhance a federal sentence is a 

“matter of fact” that could trigger this one-year limitation period. 544 U.S. 295, 302 (2005). “[T]he period begins when a petitioner receives notice of the order vacating the prior conviction, provided that he has sought it with due diligence in state 

court, after entry of judgment in the federal case with the enhanced sentence.” Id. at 298.

On appeal, the government argues for the first time that 

Arreola-Castillo’s petition is untimely under § 2255(f)(4) be-
No. 17-1439 5

cause he did not diligently pursue vacatur of his state convictions.1 Despite two years of litigation below, the government 

never made this timeliness argument in the district court. Instead, it moved to dismiss Arreola-Castillo’s petition on the 

ground that it was an unauthorized successive motion under 

§§ 2244 and 2255(h). When that failed, the government argued 

that § 851(e) barred Arreola-Castillo’s challenge. 

We are not required to address the government’s belated 

timeliness argument. The statute of limitations in § 2255(f)(4) 

is not a jurisdictional requirement, but rather an affirmative 

defense. Estremera v. United States, 724 F.3d 773, 775 (7th Cir. 

2013). As a general rule, a defendant must raise a statute of 

limitations defense in their answer. Day v. McDonough, 547 

U.S. 198, 207–08 (2006) (citing Fed. R. Civ. P. 8(c), 12(b), 15(a)). 

Failure to do so results in forfeiture. Id. Accordingly, “courts 

are under no obligation to raise the time bar sua sponte.” Id. at 

205. 

Nevertheless, we have discretion to examine the timeliness of a habeas petition “when extraordinary circumstances 

so warrant.” Wood v. Milyard, 566 U.S. 463, 471, 473 (2012) (citing Day, 547 U.S. at 201). “[L]eeway” is appropriate in this 

context because the statute of limitations “implicat[es] values 

beyond the concerns of the parties.” Id. at 472 (second alteration in original) (quoting Day, 547 U.S. at 205). It “promotes 

judicial efficiency and conservation of judicial resources, safeguards the accuracy of state court judgments by requiring resolution of constitutional questions while the record is fresh, 

 1 The government does not dispute that Arreola-Castillo filed his 

§ 2255 petition within one year of receiving notice of the orders vacating 

his state convictions. 
6 No. 17-1439

and lends finality to state court judgments within a reasonable time.” Id. (quoting Day, 547 U.S. at 205–06). Although Day 

and Wood involved state prisoners’ habeas petitions under 28 

U.S.C. § 2244, we have assumed that those cases apply equally 

to federal prisoners’ habeas petitions under § 2255. See, e.g., 

Ryan v. United States, 688 F.3d 845, 848 (7th Cir. 2012). 

This discretion is limited in several important respects. 

First and foremost, “a federal court does not have carte blanche 

to depart from the principle of party presentation basic to our 

adversary system.” Wood, 566 U.S. at 472. Thus, although we 

may consider a timeliness argument that was inadvertently 

forfeited, “[i]t would be ‘an abuse of discretion ... to override 

a State’s deliberate waiver of a limitations defense.’” Id. at 

472–73 (quoting Day, 547 U.S. at 202). In other words, “a court 

of appeals is entitled to deny collateral relief on a procedural 

ground that the prosecutor has forfeited by overlooking it, but 

not on a ground that the prosecutor has waived.” Ryan, 688 

F.3d at 848. 

Second, even if the government accidentally forfeits a 

timeliness argument, our “power to decide an appeal on a forfeited ground should be used only in exceptional cases.” Id.

We have “good reason” to “abstain from entertaining issues 

that have not been raised and preserved in the court of first 

instance.” Wood, 566 U.S. at 473. “That restraint is all the more 

appropriate when the appellate court itself spots an issue the 

parties did not air below.” Id. In addition, we must give “[d]ue 

regard for the trial court’s processes and time investment.” Id. 

After all, “[i]t typically takes a district court more time to decide a habeas case on the merits, than it does to resolve a petition on threshold procedural grounds.” Id. When a court of 

appeals belatedly interjects a procedural impediment after 
No. 17-1439 7

resolution on the merits, “the district court’s labor is discounted.” Id. at 474. Perhaps even more troubling, “the appellate court acts not as a court of review but as one of first view.” 

Id.

Here, the government argues that its failure to pursue a 

timeliness argument under § 2255(f)(4) was an unintentional 

“misstep.” Accordingly, it contends that it merely forfeited 

the argument. Arreola-Castillo, on the other hand, argues for 

waiver. In the event we find forfeiture, Arreola-Castillo argues that we should not exercise our discretion to address the 

timeliness issue. 

Ultimately, we need not decide the issue. Even if the government merely forfeited the timeliness argument, we would 

not exercise our discretion to address it sua sponte. The government does not cite a single case in which we have exercised 

our discretion to address a forfeited timeliness argument in a 

habeas case on appeal. We have, however, declined to exercise 

that discretion on at least two occasions. See Turner v. United 

States, 693 F.3d 756, 758–59 (7th Cir. 2012); Hill v. Werlinger, 695 

F.3d 644, 647 (7th Cir. 2012). As in those cases, the government

“has presented nothing to show that this is an ‘exceptional 

case’ in which we should base our decision on a forfeited 

ground.” Hill, 695 F.3d at 647 (quoting Wood, 566 U.S. at 473). 

The government argues that the record already contains the 

relevant facts. But that hardly renders this case exceptional. 

Furthermore, Arreola-Castillo might have submitted additional evidence of his diligence had the government raised the

timeliness objection in the district court. We decline to penalize him now for substantiating his claims despite the government’s oversight. The government also claims that we should 
8 No. 17-1439

exercise our discretion to “avoid a potentially difficult statutory construction question with a lurking circuit split behind 

it.” However, as explained infra, the only published federal 

court of appeals decision on this issue favors Arreola-Castillo’s interpretation. And even if we took the other circuit’s 

nonprecedential order into account, we would at most be lining up on one side of a debate. In this context, we see no reason to avoid such a step.

In sum, we have good reason to exercise our normal restraint in this context. The district court presided over this 

case for two years and ultimately resolved it on the merits. 

Were we to dismiss the case on a procedural ground at this 

juncture, we would effectively discount the district court’s efforts. Therefore, we exercise our discretion to proceed to the 

merits of Arreola-Castillo’s habeas petition. 

B. Section 851(e) Does Not Apply to a § 2255 Petition to 

Reopen a Federal Sentence Based on the Vacatur of 

Enhancing State Convictions 

Turning to the merits, Arreola-Castillo argues that the district court erred by holding that § 851(e) bars an individual 

from reopening his federal sentence under § 2255 when the 

state convictions that enhanced the sentence have since been 

vacated. We review that question of statutory interpretation 

de novo. United States v. Ford, 798 F.3d 655, 661 (7th Cir. 2015).

1. Statutory Framework

Section 841(b) outlines the penalties for federal drug 

crimes based upon the quantity of drugs involved and the 

number of prior drug convictions. See 21 U.S.C. § 841(b). 

When a drug offense involves 1,000 kilograms or more of marijuana, the statutory sentencing range is ten years to life in 
No. 17-1439 9

prison. Id. § 841(b)(1)(A). If the defendant has two or more

prior convictions for a felony drug offense, the penalty becomes a mandatory life sentence. Id.

To impose a recidivism penalty under § 841, the government must follow the procedures in 21 U.S.C. § 851. Under 

that section, the United States attorney must file an information with the sentencing court stating the previous convictions to be relied upon. Id. § 851(a). If an information is filed, 

“the court shall ... inquire of the person with respect to whom 

the information was filed whether he affirms or denies that he 

has been previously convicted as alleged in the information.” 

Id. § 851(b). “If the person denies any allegation of the information of prior conviction, or claims that any conviction alleged is invalid, he shall file a written response ... .” Id.

§ 851(c)(1). “Any challenge to a prior conviction, not raised by 

response to the information before an increased sentence is 

imposed in reliance thereon, shall be waived unless good 

cause be shown for failure to make a timely challenge.” Id.

§ 851(c)(2).

If the person files a response, “[t]he court shall hold a hearing to determine any issues raised by the response which 

would except the person from increased punishment.” Id.

§ 851(c)(1). At the hearing, the parties may present evidence 

and request that the court make findings of fact and conclusions of law. Id. “If the court determines that the person has 

not been convicted as alleged in the information, that a conviction alleged in the information is invalid, or that the person 

is otherwise not subject to an increased sentence as a matter 

of law,” the United States attorney may appeal that determination. Id. § 851(d). 
10 No. 17-1439

Section 851 also includes the following statute of limitations: “No person who stands convicted of an offense under 

this part may challenge the validity of any prior conviction 

alleged under this section which occurred more than five 

years before the date of the information alleging such prior 

conviction.” Id. § 851(e).

2. The Statutory Text Distinguishes Between Challenging 

the Validity of a Prior Conviction and Disputing the Fact 

of a Prior Conviction 

The parties dispute whether the five-year statute of limitations in § 851(e) applies to Arreola-Castillo’s § 2255 petition. 

The answer to this question turns on whether Arreola-Castillo’s habeas petition “challenge[s] the validity of any prior 

conviction.” Id. If so, it is clearly barred by § 851(e) because 

the government filed the information alleging his prior convictions in 2006—more than five years after the prior convictions occurred in 1996. However, Arreola-Castillo argues that

because the state court already vacated his prior convictions, 

he is no longer challenging the validity of those convictions, 

but rather their very existence. Accordingly, he claims that 

§ 851(e) does not apply. 

To resolve this dispute, we must “begin[] with the plain 

language of the statute.” United States v. Berkos, 543 F.3d 392, 

396 (7th Cir. 2008). Here, the statutory language supports Arreola-Castillo’s interpretation. Section 851 repeatedly distinguishes between denying the fact of a prior conviction, on the 

one hand, and challenging the validity of a prior conviction, 

on the other. For example, under § 851(c)(1), a person may respond to an information by either “den[ying] any allegation 

of the information of prior conviction, or claim[ing] that any 

conviction alleged is invalid.” 21 U.S.C. § 851(c)(1). Likewise, 
No. 17-1439 11

under § 851(d)(2), the sentencing court may “determine[] that 

the person has not been convicted as alleged in the information, that a conviction alleged in the information is invalid, 

or that the person is otherwise not subject to an increased sentence as a matter of law.” Id. § 851(d)(2). The statute’s persistent use of the disjunctive “or” when describing these concepts suggests that denying the fact of a prior conviction and 

challenging the validity of a prior conviction must be given 

separate meanings. See Reiter v. Sonotone Corp., 442 U.S. 330, 

339 (1979) (“Canons of construction ordinarily suggest that 

terms connected by a disjunctive be given separate meanings

... .”). Critically, although § 851(e) bars an individual from 

challenging “the validity of any prior conviction” that is more 

than five years old, it in no way limits an individual’s ability 

to deny that such a conviction exists. 21 U.S.C. § 851(e). 

In addition, § 851’s use of the word “challenge” is instructive. “The word ‘challenge’ is used only three other times in 

§ 851, once in § 851(b) and twice in § 851(c)(2).” United States 

v. McChristian, 47 F.3d 1499, 1503 (9th Cir. 1995). In § 851(b), it 

is “ambiguous” whether the word “challenge” would include 

a showing that the prior conviction has been vacated in state 

court. Id.2 However, the use of “challenge” in § 851(c)(2) provides more insight into what the drafters intended that word 

to mean. See id. Section 851(c)(2) outlines the steps a defendant 

must take if he “claim[s] that a conviction alleged in the information was obtained in violation of the Constitution of the 

 2 To the extent one could argue that § 851(b) uses the term “challenge” 

more broadly than § 851(c), at most that would suggest that there is some 

ambiguity in the statute. The context and purpose of the law taken as a 

whole, however, suggest that the word “challenge” normally means a 

“full-blown attack,” for the reasons we have explained.
12 No. 17-1439

United States.” 21 U.S.C. § 851(c)(2). In that scenario, the defendant must “set forth his claim, and the factual basis therefor, with particularity in his response to the information.” Id.

The provision also establishes the burden of proof (preponderance of the evidence) with respect to any factual issues 

raised in the response. Id. In the very next sentence, § 851(c)(2) 

refers to this situation as a “challenge to a prior conviction.” 

Id. The reference to pleading requirements and the burden of 

proof suggests that the word “challenge,” as used in 

§ 851(c)(2), “means only a full-blown, collateral attack in federal court on the prior conviction.” McChristian, 47 F.3d at 

1503. It follows that “challenge” means the same in § 851(e). 

See United States v. LaFaive, 618 F.3d 613, 617 (7th Cir. 2010) 

(“Absent evidence of Congress’s intent to the contrary, we assume that Congress intended the same words used close together in a statute to have the same meaning.”). Where, as 

here, a state court has vacated the prior convictions, the petitioner is not launching a full-blown collateral attack in the federal court. Rather, he has already successfully challenged the 

validity of those convictions in state court and is simply asking the federal court to recognize the state court’s determination. 

Looking at § 851(e) in isolation, the government argues 

that denying the existence of a vacated conviction necessarily 

entails challenging the validity of that conviction. To support 

this argument, the government points to various dictionary 

definitions of the term “validity.” However, this argument 

fails for two reasons. 

First, some of the proffered definitions of “validity”—e.g., 

“the quality or state of being valid”—are unhelpful tautolo-
No. 17-1439 13

gies. Validity, Merriam-Webster Dictionary, http://www.merriam-webster.com/dictionary/validity (last visited May 2, 

2018). Other definitions—e.g., “the quality of being wellgrounded, sound, or correct” and “meritorious”—actually 

support Arreola-Castillo’s position. Id..; Valid, Black’s Law 

Dictionary (10th ed. 2014). If valid means meritorious, then a 

vacated “conviction ha[s] no ‘validity’ that could be challenged,” and “any challenge in federal court to the validity of 

that conviction would have been moot.” McChristian, 47 F.3d 

at 1503.

Second, by offering definitions of validity that are completely untethered from how that word is used elsewhere in 

the statute, the government violates “the cardinal rule that a 

statute is to be read as a whole.” King v. St. Vincent’s Hosp., 502 

U.S. 215, 221 (1991). “[S]tatutes ‘should not be read as a series 

of unrelated and isolated provisions.’” Gonzales v. Oregon, 546 

U.S. 243, 273 (2006) (quoting Gustafson v. Alloyd Co., 513 U.S. 

561, 570 (1995)). “[T]he meaning of statutory language, plain 

or not, depends on context.” King, 502 U.S. at 221. As explained supra, § 851 repeatedly refers to the validity of a conviction and the fact of a conviction as separate and mutually 

exclusive concepts. To the extent there is a conflict between 

the use of the word “validity” in the statute and generic dictionary definitions, the statutory characterization prevails. See 

Cent. States, Se. & Sw. Areas Pension Fund v. Fulkerson, 238 F.3d 

891, 895 (7th Cir. 2001) (“Statutory terms or words will be construed according to their ordinary, common meaning unless 

these are defined by the statute or the statutory context requires a different definition.”). 

Finally, it is important to note that § 851(e) does not speak 

of the ability to file a case attacking the prior conviction. It 
14 No. 17-1439

would be extraordinary for a federal statute to forbid a person 

from going to state court and properly filing an action that the 

state court is prepared to entertain. At the very least, one 

would expect a clear statement from Congress that such a profound interference with the state-court system was contemplated. Nothing in § 851(e) comes close to a clear statement 

permitting the federal courts, in effect, to enjoin someone 

from filing a motion for relief in state court. Cf. 28 U.S.C. 

§ 2283. Our interpretation of the statute respects this important federalism concern.

3. Our Precedent Further Supports This Interpretation of 

§ 851(e)

When interpreting a statutory phrase, we also “consult[] 

any precedents or authorities that inform the analysis.” Kasten 

v. Saint-Gobain Performance Plastics Corp., 563 U.S. 1, 7 (2011) 

(quoting Dolan v. Postal Serv., 546 U.S. 481, 486 (2006)). Here, 

our precedent reinforces the statute’s distinction between 

challenging the validity of a prior conviction and denying the 

existence of a prior conviction. 

For example, in United States v. Arango-Montoya, we held 

that § 851(e) applies to the former but not the latter. 61 F.3d 

1331, 1339 (7th Cir. 1995). The defendant in that case claimed 

that his prior state conviction was invalid because it was the 

result of an involuntary guilty plea. Id. at 1333. He maintained

that even if § 851(e) prevented him from collaterally attacking 

the prior conviction because it was more than five years old,

the sentencing court was still required to follow the procedural requirements in § 851(b) and (c). Id. at 1339. We held 

that the sentencing court’s failure to follow those procedures 

was “harmless” because § 851(e) barred the defendant from 

challenging the validity of his prior conviction, anyway. Id. 
No. 17-1439 15

However, we held that the sentencing court still had to ask the 

defendant whether he affirmed or denied the prior conviction 

as required by § 851(b), “even if § 851(e) bars a collateral attack on the prior conviction.” Id. We noted that this requirement is necessary because “it is always possible that the government was mistaken and there was no prior conviction, or 

that the facts alleged in the government’s information of prior 

conviction are incorrect.” Id. Therefore, under Arango-Montoya, an individual may deny the existence of a prior conviction even if the five-year statute of limitations in § 851(e) prevents him from challenging the validity of that conviction. 

Similarly, in United States v. Elder, 840 F.3d 455 (7th Cir. 

2016), we suggested that an individual may challenge the existence of a qualifying conviction without impermissibly challenging the validity of the prior conviction. In that case, the 

government filed an information under § 851 alleging that the 

defendant had two prior state convictions that involved felony drug offenses. Id. at 458. Both of those prior convictions 

were more than five years old, and the defendant did not attempt to challenge their validity at sentencing. Id. Pursuant to 

the recidivism provisions of § 841, the sentencing court imposed a mandatory life sentence of imprisonment. Id. On appeal, the defendant argued that one of the prior convictions 

“was not a conviction for a felony drug offense” within the 

meaning of § 841 “because it was not punishable by more than 

one year imprisonment.” Id. at 461. We agreed and accordingly vacated the defendant’s mandatory life sentence. Id.

Even though the prior conviction was more than five years 

old, we did not address whether § 851(e) barred the defendants claim. Presumably, we did not need to because the defendant was not challenging the validity of the prior conviction. 
16 No. 17-1439

4. Two of Our Sister Circuits Have Adopted This Interpretation of § 851(e)

Our sister circuits have reached similar conclusions. In 

McChristian, the Ninth Circuit held that § 851(e) did not preclude the defendant from claiming that his prior conviction, 

which was more than five years old, had been stricken by the 

state court. 47 F.3d at 1503. The Ninth Circuit reached this conclusion for several reasons. First, the court noted that, because 

the state court struck the prior conviction, “any challenge in 

federal court to the validity of that conviction would have 

been moot.” Id. Second, based on “a careful reading of the 

statute,” the court concluded that “§ 851(e)’s purpose was to 

exclude from federal court only collateral challenges to convictions and not reports of successful collateral challenges 

completed in state court.” Id. In particular, the court relied on 

how the word “challenge” is used in § 851. Id. Finally, the 

court explained that, because the defendant’s prior conviction 

was stricken before his federal sentencing, any concerns about 

finality were “inapposite.” Id. Indeed, the court could “think 

of no government interest in enhancing a defendant’s sentence based on a prior conviction that has already been shown 

to be obtained in violation of the Constitution.” Id.

More recently, the Second Circuit also suggested in an unpublished decision that there is a distinction between challenging the fact of a conviction and the validity of a conviction 

under § 851. In United States v. Gabriel, the defendant claimed 

that the district court procedurally erred by failing to ask 

whether he affirmed or denied his prior conviction. 599 F. 

App’x 407, 407 (2d Cir. 2015). The defendant sought, but did 

not achieve, vacatur of the prior conviction in state court. Id.

at 408. Because the defendant did not dispute the fact of his 
No. 17-1439 17

prior conviction, the Second Circuit held that he was not prejudiced by the alleged procedural error. Id. The court further 

noted that the defendant “could not challenge the validity (as

opposed to the fact) of his prior felony conviction because it 

occurred more than five years before the filing of the prior felony information.” Id. (citing 21 U.S.C. § 851(e)). Although the 

Second Circuit did not address the precise issue presented 

here, it intimated that a defendant may dispute the fact of a 

prior conviction even if § 851(e) barred the defendant from 

challenging its validity. 

Only the Eleventh Circuit, also in an unpublished decision, has reached the opposite conclusion. See St. Preux v. 

United States, 539 F. App’x 946 (11th Cir. 2013) (per curiam). In 

St. Preux, the court held that § 851(e) barred a federal prisoner 

from reopening his federal sentence after the state court vacated the prior conviction that enhanced his federal sentence. 

Id. at 948. The court stated that “the plain language” of 

§ 851(e) barred the prisoner’s claim because the prior conviction occurred more than five years before the government 

filed its information. Id. It distinguished the Ninth Circuit’s 

decision in McChristian because, in that case, the prior conviction was vacated prior to the federal sentencing hearing. Id. at 

949. Although the timing in McChristian diminished the finality interests at stake, the Ninth Circuit focused primarily on 

“a careful reading of the statute,” in particular § 851’s use of 

the word “challenge.” McChristian, 47 F.3d at 1503. The St. 

Preux court did not even attempt to grapple with this statutory interpretation question. Nor did it provide any other reasoning for its conclusion. Accordingly, we do not find it persuasive. 
18 No. 17-1439

5. The Government’s Negative Implications Argument Is 

Not Convincing

Lacking support from the statutory text and case law, the 

government argues that negative implications from other 

statutes and the Sentencing Guidelines support its interpretation. Another recidivism statute—the Armed Career Criminal 

Act of 1984 (“ACCA”)3—provides that “[a]ny conviction 

which has been expunged, or set aside or for which a person 

has been pardoned or has had civil rights restored shall not 

be considered a conviction for purposes of this chapter.” 18 

U.S.C. § 921(a)(20). Similarly, the Sentencing Guidelines expressly preclude consideration of vacated convictions when 

calculating a defendant’s criminal history or determining 

whether they are a career offender. See U.S.S.G. § 4A1.2 cmt. 

n.6. Because both the ACCA and Sentencing Guidelines explicitly exclude vacated convictions, the government argues 

that Congress knows how to preclude courts from considering them when it so desires. Accordingly, the government 

claims that the omission of similar language from § 851 suggests that Congress intended to preclude all challenges to 

prior convictions that are more than five years old, including 

vacated convictions. 

This argument is unavailing. Indeed, the only authority 

that has endorsed this negative implications argument is the 

dissenting voice in McChristian. See 47 F.3d at 1509–10 (Hall, 

J., dissenting in part). And the majority in that case found that 

the statutory text compelled the opposite conclusion. See id. at 

 3 The ACCA increases the penalty for possession of a firearm by a 

felon if the defendant has prior convictions for a violent felony or a serious 

drug offense. 18 U.S.C. § 924(e). 
No. 17-1439 19

1503. True, § 851(e) does not use the exact language found in 

the ACCA. However, this is hardly surprising given that § 851 

was enacted in 1970—almost sixteen years before the ACCA 

was amended to prohibit consideration of vacated convictions. See Pub. L. No. 91-513, 84 Stat. 1269 (codified at 21 

U.S.C. § 851); Pub. L. No. 99-308, 100 Stat. 449 (codified at 18 

U.S.C. § 921(a)(20)). Moreover, although we presume that 

Congress acts intentionally when it “includes particular language in one section of a statute but omits it another section 

of the same Act,” that is not the case here. Russello v. United 

States, 464 U.S. 16, 23 (1983) (quoting United States v. Wong Kim 

Bo, 472 F.2d 720, 722 (1972)). Here, the government relies on 

language used in a different federal statute to support its interpretation of § 851(e). Accordingly, its negative implications argument is entitled to less weight. Finally, the government’s reliance on language in the Sentencing Guidelines is misplaced 

because that language is written by the Sentencing Commission—an independent agency within the judicial branch—not

Congress. Therefore, the government’s attempt to glean congressional intent based on language in the Sentencing Guidelines is unpersuasive. 

Ultimately, although § 851(e) does not use the same language as the ACCA or the Sentencing Guidelines, it achieves 

the same result by distinguishing between challenges to the 

validity of a prior conviction and claims that a prior conviction does not exist. Under the language of § 851 and our own 

precedent interpreting that provision, the five-year statute of 

limitations in § 851(e) applies to the former but not the latter. 

6. Section 851 Does Not Preclude Habeas Review

Next, the government contends that § 851 is the “exclusive 

means” for challenging prior convictions such that Arreola-
20 No. 17-1439

Castillo may not use § 2255 as a vehicle to adjust his federal 

sentence. 

In support of this argument, the government relies on 

United States v. Roberson, 684 F. Supp. 2d 179 (D. Mass. 2010). 

Like Arreola-Castillo, the defendant in Roberson filed a habeas 

petition under § 2255 seeking to set aside his federal sentence 

under 21 U.S.C. § 841 after a state court vacated the prior conviction that enhanced his sentence. Id. at 180–81. However, the 

government argued that the defendant could not seek habeas 

relief on that ground because § 851 provides the exclusive 

procedure for challenging a prior conviction. Id. at 182. The 

district court acknowledged that several Supreme Court cases 

“generally support the proposition that an enhanced federal 

sentence may be adjusted on a § 2255 motion after the enhancing prior conviction has been vacated.” Id. Nevertheless, the 

court ultimately concluded that “Congress intended the provisions of § 851 to provide the exclusive basis and procedures 

for challenging such a prior conviction as it pertains to the enhancements for federal drug crimes authorized under 

§ 841(b)(1)(A) and (B).” Id. at 189. This was so, the court explained, because the waiver provision in § 851(c)(2) does not 

include an exception allowing an individual to later seek federal habeas relief under § 2255. Id. at 186. In addition, the court 

reasoned that § 851(e)’s statute of limitations would “serve[] 

no purpose” if an individual could later move for resentencing under § 2255. Id. at 187. Finally, the court interpreted the 

“detailed provisions” in § 851(b) as “the equivalent of advice 

to ‘speak now or forever hold your peace.’” Id. at 188. The 

court conceded, however, that its “attempt to understand congressional intent [was] indirect and inferential, and ... thus 

not a certain thing.” Id.
No. 17-1439 21

In addition to being nonbinding on this Court, there is a 

critical flaw in the Roberson court’s reasoning: “Implications 

from statutory text or legislative history are not sufficient to 

repeal habeas jurisdiction.” I.N.S. v. St. Cyr, 533 U.S. 289, 299 

(2001). Rather, “Congress must articulate specific and unambiguous statutory directives to effect a repeal.” Id. Accordingly, to the extent the government argues that § 851 precludes Arreola-Castillo from seeking habeas relief, it must 

point to “a particularly clear statement that such is Congress’ 

intent.” Demore v. Kim, 538 U.S. 510, 517 (2003). The government cannot do so here because § 851 does not even mention, 

let alone expressly foreclose, either habeas relief under § 2255

or resort to a state court consistent with that court’s rules. See 

21 U.S.C. § 851. 

Moreover, the Supreme Court has consistently held in 

other statutory contexts that an individual may move to reopen a federal sentence based on the state court’s vacatur of a 

prior conviction that enhanced the sentence. For example, in 

Custis v. United States, the Supreme Court held that, under the 

ACCA, defendants may not collaterally attack the validity of 

a prior conviction during a federal sentencing hearing. 511 

U.S. 485, 490–94 (1994).4 Nevertheless, although the ACCA 

“[did] not permit [the defendant] to use the federal sentencing 

forum to gain review of his state convictions,” the Court 

noted that he “may attack his sentences in Maryland or 

through federal habeas review.” Id. at 497. The Court continued: “If [the defendant] is successful in attacking these state 

 4 The Court distinguished the ACCA from § 851, which allows an individual to challenge the validity of a prior conviction that is less than five 

years old. See Daniels, 511 U.S. at 491. 
22 No. 17-1439

sentences, he may then apply for reopening of any federal 

sentence enhanced by the state sentences.” Id.

In Daniels v. United States, the Court reaffirmed that 

“[a]fter an enhanced federal sentence has been imposed pursuant to the ACCA, the person sentenced may pursue any 

channels of direct or collateral review still available to challenge his prior conviction,” including state court. 532 U.S. 374, 

382 (2001). “If any such challenge to the underlying conviction 

is successful, the defendant may then apply for reopening of 

his federal sentence.” Id.5

Finally, in Johnson v. United States, the Court said that Custis and Daniels “assume[d] ... that a defendant given a sentence enhanced for a prior conviction is entitled to a reduction 

if the earlier conviction is vacated.” 544 U.S. at 303. The Johnson court reiterated that “a defendant who successfully attacked his state conviction in state court or on federal habeas 

review could then ‘apply for reopening of any federal sentence enhanced by the state sentences.’” Id. (quoting Custis, 

511 U.S. at 497). Although these decisions involved the 

ACCA, the government does not point to anything in § 851 to 

support a contrary conclusion here. 

 5 Unlike Arreola-Castillo, who successfully sought vacatur of his prior 

convictions in state court, the petitioner in Daniels “failed to pursue remedies that were otherwise available to him to challenge his [prior] convictions.” 523 U.S. at 384. Having failed to do so, the Court held that he could 

not use § 2255 to attack those convictions. Id.
No. 17-1439 23

7. The Statutory Purpose Further Supports this Interpretation 

Finally, we consider the purpose of § 851(e). See Senne v. 

Village of Palatine, 695 F.3d 597, 601 (7th Cir. 2012) (“Interpretation of a word or phrase depends upon reading the whole 

statutory text, considering the purpose and context of the statute[] ... .” (alterations in original) (quoting Dolan, 546 U.S. at

486)).

The purpose of § 851(e) is twofold. First, it prevents administrative difficulties. By keeping collateral challenges to 

old convictions out of the federal courts after a specified time, 

§ 851(e) mitigates the “expense of keeping court records indefinitely, concerns about evidence being lost over time, and 

‘thorny procedural difficulties’ at sentencing hearings.” 

McChristian, 47 F.3d at 1503 (quoting United States v. Davis, 36

F.3d 1424, 1438 (9th Cir. 1994)). The Daniels Court, interpreting 

the ACCA, worried whether a district court would “have the 

documents necessary to evaluate claims arising from longpast proceedings in a different jurisdiction.” 532 U.S. at 379. 

In Custis, the Court similarly expressed a concern that, if defendants were allowed to attack a prior conviction during federal sentencing, this “would require sentencing courts to rummage through frequently nonexistent or difficult to obtain 

state-court transcripts or records that may date from another 

era, and may come from any one of the 50 states.” 511 U.S. at 

496. However, the Custis Court recognized an exception for 

claims based on failure to appoint counsel, in part because the 

basis for such claims “will generally appear from the judgment roll itself, or from an accompanying minute order.” Id.
24 No. 17-1439

Second, § 851(e) protects the finality of state court judgments. States “have a real and continuing interest in the integrity of [their] judgments.” Daniels, 532 U.S. at 380. “By challenging the previous conviction, the defendant is asking a district court to deprive the state-court judgment of its normal 

force and effect in a proceeding that has an independent purpose other than to overturn the prior judgment.” Custis, 511 

U.S. at 497 (internal quotation marks and alterations omitted). 

In the ACCA context, the Supreme Court was concerned that

such a collateral attack “would effectively permit challenges 

far too stale to be brought in their own right, and sanction an 

end run around statutes of limitations and other procedural 

barriers that would preclude the movant from attacking the 

prior conviction directly” in state court. Daniels, 532 U.S. at 

383. 

Neither of those concerns are implicated where, as here, 

the petitioner directly attacked the prior conviction in state 

court and the state court vacated the prior conviction. The 

government complains that the state court case files have been 

archived or discarded and that, due to the passage of time, 

victims may be unavailable or unwilling to testify. Critically, 

though, Arreola-Castillo is not asking the district court to 

rummage through old case files and hear from witnesses to 

determine whether his prior convictions were invalid. The 

New Mexico state court already adjudicated the matter and 

vacated his prior convictions on that ground. Now, ArreolaCastillo is simply asking the district court to look at the state 

court’s orders to that effect. Like a claim based on failure to 

appoint counsel, a claim based on vacatur of a prior state conviction will be apparent from the state court’s orders. Moreover, there is no concern about protecting the finality of state 

court judgments because New Mexico already deprived its 
No. 17-1439 25

own judgments of force and effect by vacating them. In doing 

so, the New Mexico state court clearly determined that Arreola-Castillo’s claims did not run afoul of the state’s statutes of 

limitations and procedural barriers. 

III. Conclusion

For the foregoing reasons, we REVERSE the judgment of the 

district court.