Here's what we can say for sure: John Boehner may or may not retire at the end of this term. But Boehner does not want to go down as the guy who managed the two least-productive, least-popular congresses of all time, and whose greatest accomplishments were convincing his members not to shut down the government or breach the debt ceiling. According to the Huffington Post, before he retires, he wants at least one legacy-building accomplishment. He'll even stay in Congress to get it.
"Sources also universally agreed that the one thing that would keep him in place through 2016, if he could somehow manage to win, is the possibility of locking in a grand bargain that cuts entitlement programs and spending generally," write Grim and Ward.
But this isn't like waiting to draw an inside straight or hoping it'll rain tomorrow. If Boehner wants a major, legacy-ready deal, he just needs to cut one, lift the Hastert rule and let it come to a vote.
That deal could be immigration reform. It could be a grand bargain. Either way, Boehner's legacy is in Boehner's power to secure. The coming fiscal crack-up — in which Congress will have to fund the government, raise the debt ceiling and manage (or replace) sequestration all at the same time — would seem to provide a perfect opportunity.
The reason that deal won't happen — at least not in a "grand bargain" way — is that the two sides really, honestly, seriously disagree about what constitutes a good deal, and they're still bitter over the failures of past deals.
Team Boehner still views the offer they made to President Obama after the fiscal cliff — $1 trillion in taxes the administration wanted for $1 trillion in cuts both sides could agree to — as more than fair, and the White House's rejection of that offer as inexplicable. The White House, of course, disagreed, and the end result was $600 billion in taxes alongside $1 trillion in sequestration cuts that both sides hate. So in addition to honest disagreements over fiscal issues, there's also a lot of resentment, and a lot of past positions neither side intends to back down from.
All of which would suggest that the right place for Boehner to make a deal is immigration reform. While Boehner really does think the White House deals on the budget in bad faith and wants too much in taxes, he doesn't personally find the Senate's immigration compromise to be noxious policy. And the votes really are there for it, or something like it, if Boehner chose to lift the Hastert rule.
Moreover, cutting a deal on immigration would do less harm to Boehner's long-term prospects inside the Republican Party. While a deal that raised taxes would be seen as a genuine betrayal, much of Republican Washington — and Boehner will almost certainly become part of Republican Washington after he retires — would applaud a deal on immigration, seeing it as nothing less than a key step towards saving the future of their party. Boehner could retire as a hero rather than as a heretic or a failure.