Speaker of the House John Boehner is expected, by former aides, to step down from his leadership position after the 2014 mid-term elections. There is some speculation that he might not even run for re-election in 2014 but that seems unlikely. Even if he stays after the 2014 mid-terms, almost nobody expects him to maintain being the Speaker after 2016.
Speaker Boehner narrowly got re-elected to being Speaker of the House in January of 2013. The close election in the House was described by the political blog Five Thirty-Eight as historic. There was such rampant speculation that Boehner would not be re-elected as Speaker that some people, like me, started a Speaker of the House power rankings. Ultimately, many of the Tea Party and further right-wing lawmakers who claimed that they would not re-elect Boehner as Speaker got cold feet and Boehner got re-elected with 220 votes, two more than he needed. While current House Majority Leader, Eric Cantor, is not expected to run against him for the position, Cantor did steal many of the votes away from Boehner. Of course, some of those votes were cast for Allen West (who is not a member of Congress, anymore).
The Huffington Post argues that Speaker Boehner's most obvious reason for why he would not run for Speaker again, is that he does not have a significant chance of winning. Some of the favorites that they point out to become the new Speaker are Rep. Jeb Hensarling, Rep. Steve Scalise, Rep. Jim Jordan, Rep. Paul Ryan, and Rep. Tom Price. This is, of course, assuming Republicans win the House in the 2014 mid-term elections. Based on the inherent party advantage that the Republican party has with House elections, it seems fairly likely. The reason they are mentioned is because they serve as a go-between between Republican leadership and the Tea Party caucus.
I'll note that Speaker Boehner's popularity with Ohioans who consider themselves very conservative is 29/43, compared to a total favorability of 22/69. Most of Boehner's support comes from those who consider themselves to be somewhat conservative, 36/37. If we look at members of Congress, that's generally what we see, as well.
With the upcoming votes on Syria, immigration, debt ceiling, and the inevitability of Obamacare rolling out, it seems even more likely that Boehner will lose even more support from the very conservative wing of the Republican party. If, somehow, Boehner is able to negotiate a grand bargain with President Obama, it seems more likely that Boehner will retire before the 2014 elections, thus giving up the Speakership. But if he's not able to negotiate this, Boehner's legacy will be incomplete and it appears that he might stick around to save his legacy. I don't see that as likely. But I think Boehner is too proud to run for the Speaker's position in January of 2015, even assuming he runs in the mid-term elections.
I believe we're reaching the end of John Boehner's tenure as Speaker of the House. If I'm correct, we'll eventually have to see where he ranks all-time. This may prove difficult to do, as we'll have to separate him away from the further right wing of his party.