Does acceptance of a commutation moot a prisoner's collateral legal challenge to a prison sentence he is still serving?

The complicated question in the title of this post is the issue addressed in a complicated set of opinions issued by various members of the en banc Fourth Circuit as the full court dismissed as moot the long-running case of Raymond Surratt in US v. Surratt, No. 14-6851 (4th Cir. April 21, 2017) (available here).  As the latest opinion in Surratt reveals, I was involved in this case as an amicus, but I had largely forgotten that fact given that the Surratt panel opinion, as noted here, was decided nearly two years ago and oral argument before the en banc Fourth Circuit took place more than a year ago. 

I surmise that the en banc Fourth Circuit was deeply divided on the procedural and substantive issues that the complicated Surratt case presented and that a mootness ruling served as a convenient way to dispose of a hard case thanks to the deus ex machina of Prez Obama's grant of clemency to Raymond Surratt.  I am surely biased in this view because I served as an amicus in the case, but also because I think these passages from Judge Wynn's dissent make a pretty solid case against mootness:

Here, there is no dispute that if we vacate Petitioner’s commuted sentence and remand for resentencing, Petitioner will likely face a sentence shorter than that imposed by the commutation. In particular, whereas the President commuted Petitioner’s life sentence to 200 months’ imprisonment, Petitioner’s applicable Guidelines range is 120 to 137 months, less than his time-served.  Accordingly, Petitioner has a continuing “concrete interest” — namely, his liberty — in having us vacate his current sentence and remand for resentencing under the applicable Guidelines.  We and other courts have found arguably substantially less significant interests adequate to preclude mootness. See, e.g., Townes v. Jarvis, 577 F.3d 543, 547 (4th Cir. 2009) (holding that the petitioner’s release from prison did not moot his collateral challenge to his sentence because a favorable appellate decision could “affect the length of his parole”); Richards v. United States, 212 F.2d 453, 454 (D.C. Cir. 1954) (holding that defendant’s collateral challenge to the lower end of his sentencing range was not moot, even though defendant had already served more than that lower end, because “there is some possibility” that having a longer minimum sentence “may in some indirect way affect him adversely in the future”).

I am not alone in my view that an injustice continues by declaring this matter now moot. Indeed, the Seventh Circuit, the only circuit that appears to have squarely addressed the issue, refused to find mootness in analogous circumstances, holding that a petitioner may collaterally challenge his original sentence, notwithstanding that the challenged sentence was commuted during the course of litigating that collateral challenge, when the commuted sentence exceeds the mandatory minimum the petitioner would face if he prevailed on his collateral challenge.  See Simpson v. Battaglia, 458 F.3d 585, 595 (7th Cir. 2006); Madej v. Briley, 371 F.3d 898, 899 (7th Cir. 2004).  In Simpson, for example, after the petitioner filed a habeas petition challenging his death sentence, the Governor of Illinois commuted the petitioner’s sentence from death to life imprisonment without parole. 458 F.3d at 595.  Like the government does here, the State argued that the commutation rendered the petitioner’s collateral challenge to his sentence nonjusticiable, and therefore moot, because of the petitioner’s decreased sentence and “the executive nature of his confinement.” Id.  The Seventh Circuit rejected both arguments, explaining that because the petitioner would face a mandatory minimum of 20 years’ imprisonment if he prevailed on his collateral attack, as opposed to the life sentence imposed by the Governor, “it [wa]s possible for [the petitioner] to obtain relief, and his sentencing claims [we]re not moot.” Id. Put differently, “[a] full remedy for the constitutional shortcoming at the original sentencing hearing entails allowing [the petitioner] to seek that lower sentence now.” Id. (second alteration in original) (quoting Madej, 371 F.3d at 899).

I presume Raymond Surratt could opt to seek Supreme Court review of the Fourth Circuit's decision that his collateral challenge to his old/new sentence is moot. But, ironically, the Fourth Circuit's mootness claim may arguably get stronger in the very process of cert review, at least functionally if not legally, because Surratt likely will have finished serving his 200 months in federal prison by the time the Supreme Court could get around to taking up and hearing Surratt's challenge to the Fourth Circuit's mootness conclusion.