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Federal District Court Finds ‘Confusion’ Over Law in State Court Excused Late Filing of § 2255 Motion

Finding confusion in the state courts over the status of the law and obstacles put in place by the federal prison system that hindered filing for relief, the U.S. District Court for the District of Vermont granted resentencing, excusing the late filing of a motion to vacate a sentence under 28 U.S.C. § 2255.

Federal prisoner Shawn Simard filed a motion to vacate his sentence under § 2255 after he successfully challenged a prior conviction in state court that was used to double his federal sentencing range. He had been convicted of possession of child pornography under 18 U.S.C. § 2252(a)(4)(B) and sentenced in 2012 to just over 10 years in federal prison without parole, under a 10-year mandatory minimum for having a qualifying prior sex offense in Vermont. Without the prior conviction, Simard faced up to 10 years in prison.

Simard’s motion was filed five years after his sentencing and three years after that sentence became “final,” but he argued that his motion was filed within the one-year limit of § 2255 because he had filed it within one year of the vacatur of his prior conviction by the state court.

The magistrate judge assigned to review Simard’s motion recommended dismissal of the motion as untimely, not because Simard filed it too late, but because he didn’t act with “due diligence” in getting his prior conviction vacated. Indeed, Simard’s prior was from 2004, and he didn’t file his state postconviction challenge until 2016. That years-long delay after federal sentencing before any state court challenge was filed was not diligent, the magistrate judge concluded.

But District Judge William K. Session III rejected the magistrate judge’s recommendation upon Simard’s objections, finding he was diligent in seeking vacatur of his prior conviction. The Court cited at least two reasons: (1) the state of the law about whether Simard could have successfully challenged his prior was not clear until 2017, and (2) the obstacles put in place by the federal prison system caused part of the delay in filing for relief in state court.

Section 2255’s One-Year Limit

Under § 2255(f)(4), there’s a one-year limit for filing a § 2255 motion. Most often, that one-year clock begins to run from “the date on which the judgment of conviction becomes final.” § 2255(f)(1). However, there are three other triggers that restart that one-year clock. Here, the provision under subsection (f)(4) restarted the clock for Simard: “the date on which the facts supporting the claim or claims presented could have been discovered through the exercise of due diligence.”

In Johnson v. United States, 544 U.S. 295 (2005), the Supreme Court held that vacatur of a prior conviction used to enhance a federal sentence was a “fact” for purposes of § 2255(f)(4). However, the Court also held that a movant must show diligence by challenging his prior conviction “as soon as he is in a position to realize that he has an interest in challenging the prior conviction.” The question came down to whether Simard was diligent in seeking vacatur of his prior conviction.

Confusion in the State Court Excused Simard’s Delayed Challenge to His Prior Conviction

The “lack of clarity in Vermont law” about whether Simard could have filed for relief played a major role in Simard’s diligence. At the time of his state conviction and sentencing, the law in taking a guilty plea was at odds. In State v. Yates, 726 A.2d 483 (Vt. 1999), the Vermont Supreme Court ruled that a defendant must personally admit in court the factual basis for the charge in order for his guilty plea to be valid. However, in State v. Morrissette, 743 A.2d 1091 (Vt. 1999), the Court ruled that a defendant may sign a waiver, and his attorney may admit the factual basis. The Vermont Supreme Court further ruled in State v. Cleary, 824 A.2d 509 (Vt. 2003), that as long as the defendant acknowledged the charging documents that formed the factual basis the guilty plea is valid.

In 2014, the Vermont Supreme Court began dismantling the previous line of cases, holding In re Manosh, 108 A.2d 212 (Vt. 2014), that its decision in Yates controlled, overturning Morrissette, and holding that a trial court must personally address the defendant in open court. Still not entirely clear that Yates controlled because Cleary remained good law after Manosh, the Court announced in In re Bridger, 176 A.2d 489 (Vt. 2017), that Cleary is no good, reinforcing that its Yates decision is the rule. “Unfortunately, [Morrissette and Cleary] inadvertently sowed confusion by importing the phrase ‘substantial compliance’ into our Rule 11(f) jurisprudence,” the Court explained. “‘Substantial compliance’ has no place in Rule 11(f) claims,” the Court clarified.

The problem with Simard’s prior conviction was that the trial court never asked him during the guilty plea whether he admitted to the factual basis for the charge. Instead, the court simply asked him whether he understood the charge, and counsel (not Simard) agreed to the facts.

When Manosh overturned Morrissette, he began the process of filing for relief. The state court found that Simard’s guilty plea was invalid and vacated his conviction. The state then dropped the charge.

The “due diligence” measuring stick under § 2255(f)(4) applies to how promptly a movant files for state postconviction relief; it has nothing to do with how soon he files his federal § 2255 motion. Once the prior is vacated, the § 2255(f)(4) one-year clock runs from the date of the state court’s vacatur order. The Second Circuit, and every other circuit, has held that “due diligence” does not mean “maximum feasible diligence” but only “due, or reasonable diligence.” Wims v. United States, 225 F.3d 186 (2d Cir. 2000). In other words, the court ruled that a movant is not required to “undertake repeated exercises in futility or to exhaust every imaginable option, but rather to make reasonable efforts.”

While Simard filed his state challenge 18 months after Manosh, the district court found that the state of confusion in the state courts still wasn’t cured until Bridger in 2017, though his conviction was vacated in 2016. Simard, the Court said, was “diligent” under § 2255(f)(4), considering that he also faced obstacles put in place by the federal prison system.

The Federal Prison System Hindered Simard’s Ability
to Timely File a State
Postconviction Challenge

The district court also found that the federal prison system hindered his ability to promptly file his state challenge, adding to its conclusion that he was diligent. After his federal sentencing in 2012, Simard was assaulted at least five times and sexually assaulted at least once. He spent “more than a year in the SHU cumulatively,” the Court noted, and was transferred to different prisons at least 13 times. His legal papers were also lost by staff. And when Simard asked prison staff to help him, he was referred to prisoner law clerks.

Because of the nature of his conviction, Simard feared asking for help from other prisoners. Moreover, Simard was refused stamps by prison staff to mail his court papers. Only when he was appointed counsel was his challenge properly filed in state court. Simard filed an affidavit swearing to all these facts in support of his due diligence.

The Court found these facts impeded due diligence by Simard. A court may take into account the conditions of confinement when weighing due diligence. See Wims, supra; Easterwood v. Champion, 212 F.3d 1321 (10th Cir. 2000) (courts may not “simply ignore the reality of the prison system” in assessing diligence); Rivera v. Nolan, 538 F.Supp.2d 429 (D. Mass. 2008) (“expectations about what defines due diligence from behind prison bars must be realistic”).


Finding at least two reasons to support Simard was diligent in seeking vacatur of his prior conviction, the Court found that Simard’s § 2255 motion was timely filed under § 2255(f)(4). Accordingly, the Court granted Simard’s motion to vacate his federal sentence and to resentence him without the prior conviction. See: United States v. Simard, 2019 U.S. Dist. LEXIS 191512 (D. Vt. 2019).

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