The challenge is to not only improve President Herbert Hoover's 1st term (despite the Great Depression), but also lay the groundwork for him managing to run and win a 2nd term in 1944 or the general post-war era.
I’m assuming you mean that Bryan passes on running in 1908, not that he passes?
You could also have Hoover, or someone in his administration, have the foresight to see the “Crash” building and they could try to mitigate it before it happens.
Also, if Hoover is visibly active in trying to fix things and help people, once the depression hits, his reputation is much better and years later people will more likely say “it wasn’t his fault” and “he tried to help as much as he could.” Especially, if he never says “prosperity is just around the corner” or some such stupid statement.
Sure, it's 1940, rather than 1944, and tinkering with the Depression might well butterfly WWII as we know it, but it's my best shot at getting Hoover back into the White House.
- William Jennings Bryan passes on 1908.
- Bryan runs in 1912, and wins.
- Bryan takes the US off the gold standard.
- The lack of a gold standard mitigates the Depression (let's pretend earlier events haven't butterflied Hoover or the 1929 crash).
- Because of the above, Hoover isn't as toxic, and is narrowly defeated in 1932 by Random Democrat (may or may not be Roosevelt).
- Random Democrat serves two terms.
- Hoover tries again in 1940, gets nomination as compromise candidate, wins a second term.