AHC: Henry Wallace vs. Wendell Willkie

Henry Wallace and Wendell Willkie are remarkable similar figures in some respects. Both of them were political outsiders, staunch progressives and were originally members of the other party before joining the Democrats and Republicans respectively. In addition both of them also had various scandals, Wallace's unorthodox religious beliefs and Willkie's extramarital affair, which the other parties both threatened to release during the same election.

How could we have both figures going head-to-head as the presidential candidates for their respective parties and who do you think would win?
 
Wilkie wins. Wallace was always a bit cuckoo in terms of how voters perceived him, and he was more chosen due to his administrative capabilities and also his close relationship with FDR. FDR wanted him on the ticket in ‘44, but since he was known to be in I’ll condition many were too uncomfortable with a Wallace presidency and so FDR chose in ‘44 the more moderate Truman.
 
The problem here is that Wallace was so unpopular with conservative party bosses he'd never be on the top of a national ticket unless Roosevelt had died first. Wallace easily could have been renominated for VP in 1944, making him heir to the throne when FDR dies in 1945. But of course Willkie is dead by this point so it doesn't matter for the purposes of this thread. In order for this to work, you'd need to have Wallace renominated in 1944 and a surviving Willkie. Even then, Willkie lost to Dewey in 1944 and he'd have no chance of winning the GOP nod in 1948. Perhaps had he gone through with the plan of running for NYC Mayor in 1945 as a Liberal he could have run as a third party candidate in 1948. Making the race Wallace vs. Dewey vs. Willkie vs. Thurmond. In the end, Willkie would split the vote with Wallace and hand the election to Dewey.
 
The problem here is that Wallace was so unpopular with conservative party bosses he'd never be on the top of a national ticket unless Roosevelt had died first. Wallace easily could have been renominated for VP in 1944, making him heir to the throne when FDR dies in 1945. But of course Willkie is dead by this point so it doesn't matter for the purposes of this thread. In order for this to work, you'd need to have Wallace renominated in 1944 and a surviving Willkie. Even then, Willkie lost to Dewey in 1944 and he'd have no chance of winning the GOP nod in 1948. Perhaps had he gone through with the plan of running for NYC Mayor in 1945 as a Liberal he could have run as a third party candidate in 1948. Making the race Wallace vs. Dewey vs. Willkie vs. Thurmond. In the end, Willkie would split the vote with Wallace and hand the election to Dewey.

32. Franklin D. Roosevelt (1933-1945)
33. Henry A. Wallace (1945-1949)

34. Thomas E. Dewey (1949-1957)
 
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