Alright, I went through brief bios of everyone to hold the office since 1903.
Gurney lost the office when control switched, ran for President and lost the nomination to Taft, retired when they got the House back (he was 87)
Clark lost his seat after they lost the House, then died the following spring.
Gillet gave up the Speakership to run for Senate, won and retired at the end of his term (he was 80)
Longworth died in office, though they had just lost the House (he died before the next congress was seated).
Garner gave up the speakership to be FDR’s VP, never got a chance to run for President.
Rainey died in office
Burns died in office
Bankhead died in office
Rayburn served 17 years when they controlled the House from 39 to 61, died in office
Martin was the minority leader for that same era, getting 2 cracks at speaker when the GOP briefly took the house. Lost his seat in 66 at age 78, died 2 years later.
McCormack retired while Speaker, at age 79.
Albert retired at 68 and seems to have just wanted a peaceful retirement (died 23 years later).
O’Neill retired at 74 and didn’t seek the Presidency or any other office
Wright resigned in the middle of an ethics scandal and stayed out of politics afterwards
Foley lost his seat when they lost the House in 94, and seems to have retired. He was an ambassador for Clinton’s second term, but was 75 when could have plausibly run for President.
Then Newt, who left in disgrace but still ran for President to get some book sales, Hastert who ended up in jail, Pelosi is still there, and Boehner appears to be sick of politics, so I doubt he runs in 2020 at age 70, and will probably be too old in 2024.
So of the last 18 men to leave the speakership, two made unsuccessful bids for Presidential nomination, one became a Senator then retired, one became VP then retired before FDR stopped running, 5 died in office, 4 retired in their late 70s or later, one went to jail, three rode off into the sunset (if you count Boehner), and one retired in disgrace.
So we really have 7 examples where someone was young enough and not mired in scandal, though only Newt was comparable in age to Ryan. Of those 7, 2 tried and failed, one chose the Senate, one was blocked by Clinton and then too old, and three seem to have given up the game. If Ryan isn’t ready to give up the game, there’s at least a 50/50 shot he runs for President, based on this sample, or maybe a 2/3 since he won’t be blocked by a popular president of his party until he’s too old.
Can he win the nomination if he runs? No idea, but he has lots of factors in his favor (name recognition, no scandals, retired on his own terms) and only a small sample size to guide us about how former Speakers do.
