That said, if Cuba wants to have any chance of Trump 2.0 not eventually rolling these measures back, they will have to follow through on their commitments, and may have to put even more on the table. Time will tell.

Path of least resistance for the Biden administration was to do nothing. They chose to try to do something. And that's important, even if many find the results flawed.

There is also the point that negotiating for the release of prisoners who should have never been in jail in the first place is ugly business. I get that objection. But to it I say: what's the workable alternative? In this and other contexts, I'm not sure.

They made big commitments without a single prisoner release yet taking place. That may change in the coming days, but they're already being accused of "giving away the store" and that will continue.

Finally, I'm just surprised a Biden administration that was on the back foot so often on Cuba policy would do something this dramatic, so late—just days after Maduro's widely denounced inauguration no less, at which Miguel Díaz-Canel was present.

Still, coming at a time when Cuba's govt is clamping down on private sector (again), military enterprises are trying to regain market share, and there have been blockbuster (though unconfirmed) reports of military sitting on major $ as economy craters, the optics are explosive.

The Biden administration also likely came to see economic pressure as exerted through the CRL as contributor to mass migration, instability, and human suffering (in that it impeded things like Cuba's energy imports), without any real prospect of political change on the table.

If the Cubans made CRL a non-negotiable for prisoner releases (which I can see them doing), and Biden admin is reasonably confident Trump 2.0 will reinstate CRL anyway, maybe White House saw short window of lifting it as worth it for humanitarian gain?

The biggest surprise to me, though, is the full elimination of the CRL.

That likely explains Cuba's indication it will slow walk the full slate of releases.

Full SSOT delisting takes 45 days. Cuba likely to stretch out releases over that period as "leverage" to make sure at least SSOT delisting is allowed to take effect & buy time. :-/

But on that same token, one has to wonder what Cuba thinks it can gain. If—cruelly—it has used J11 and other presos as negotiating chips, they just ostensibly laid a bunch of them on the table for changes from the Biden administration that may not last long.

Worse, even if you think SSOT delisting was overdue & right on the merits (as I do), such a late move may put a bigger target on Cuba's back for the incoming administration than was already there. Once re-listed, Congress could also try to codify the designation this time.

The obvious: Can't Trump just re-list Cuba as SSOT in the next few months? Yes. CRL and Title III could also be revived fairly quickly—within 6 months, say.

Even as all parties are denying an explicit quid pro quo, I'm surprised by the scope, timing, and rollout of the deal for several reasons.

Given parallel announcement from Havana, it has to be the prospect of significant prisoner releases—we now know more than 500.

But whether as a result of steady negotiation or a last ditch effort (from Havana?) to put a deal on the table in exchange for relief, we don't know.

Pre-November, there was some chatter Biden might do SSOT if Harris won, to take the political hit for her on his way out.

But when Trump won, the item appeared dead on arrival, and folks in D.C. were talking that way. What changed?