Seeing Montgomery and Welch as SCOTUS Teague make-up calls

A few years ago I wrote this extended article, titled "Re-Balancing Fitness, Fairness, and Finality for Sentences," which made the case for modern doctrines to be far less concerned about sentence finality, and far more concerned about punishment fitness and fairness, when new legal developments raise doubts or concerns about lengthy prison sentences.  Though I did not in that article call for the Supreme Court's Teague doctrines to be ignored, passages from it suggesting Teague's limit on retroactivity ought to be narrowly construed appeared in amicus briefs I signed in Montgomery and Welch. 

I have been pleased that Montgomery and now Welch both resulted in a significant block of Justices declaring prior Eighth And Fifth Amendment rulings fully retroactive.  But how the Court majority has gotten there has been more than a bit puzzling because, as I see, the Court keeps massaging Teague while it suggests that it is faithfully applying the doctrine.  In Montgomery, as I explain in this new commentary, six Justices signed on to an opinion (including Chief Justice Roberts) that seems, at least indirectly, to rewrite significantly the very foundational legal basis for Teague.  And, in the final line of his solo dissent in Welch today, Justice Thomas complains that the majoity opinion in Welch (which has the votes of both Chief Justice Roberts and Justice Alito) shows that "the Court keeps moving the [retroactivity] goalposts" through its "unprincipled expansion of Teague [so that] every end is instead a new beginning."

I bring all this up because, upon reading Welch, this one passage from the majority opinion stood out for a couple of reasons: 

[W]here the conviction or sentence in fact is not authorized by substantive law, then finality interests are at their weakest.  As Justice Harlan wrote, “[t]here is little societal interest in permitting the criminal process to rest at a point where it ought properly never to repose.” Mackey, 401 U. S., at 693 (opinion of Harlan, J.).

First and foremost, I am pleased and I think it potentially quite important (and in harmony with my own writings) to see the Supreme Court state expressly that "finality interests are at their weakest" when substantive law has changed and a defendant is still dealing with the consequences of the conviction or sentence based on the now-changed substantive law.  

Second, as explained in the title of this post, the quote from Justice Harlan seems especially notable here in describing the limited societal interest in "permitting the criminal process to rest at a point where it ought properly never to repose."  I suspect that Chief Justice Roberts was somewhat more comfortable with the Teague rewriting in Montgomery and that both the Chief and Justice Alito were content with the Court's work in Welch because they may have come to the conclusion the Court ultimately took unfairly long before finally finding constitutional problems with mandatory juve LWOP and the residual clause of ACCA.  In both settings, lots and lots of defendants subject to really long prison terms have been persistently complaining for decades that these extreme sentencing laws were constitutionally problematic.  I would guess that, as judicial umpires calling balls and strikes, the Chief and Justice Alito could live with a "Teague" make-up call to help the defendants who before kept getting strikes called against them.