Who could have been the most chaotic, insane and "lost" American president ever if elected?

The Great Depression happens about 18 months earlier, and Republicans are really being battered. Second Point of Departure, Al Smith Rose from the ranks of the longest convention in history to be nominated in 1924 or the Democrats are worried that they might lose with Smith even with the depression.

One of them sees Will Rogers making jokes about the mock campaign and decides to run him themselves.

Alternatively, the Democrats feel they have no chance and run him only to see the stock market crash in September of 1928 and suddenly Rogers wins a narrow victory.

I don't know the Rogers would be necessarily an apt, and it might be a funny joke more than an unfunny one, but witha Great Depression growing it might be problematic.
 
Also maybe I am just not getting it, but LeMay's "gaffe" on the 1st page just makes him look pretty good. He was asked, and true to his claims he spoke plainly and responded. Nothing really out of the ordinary here.

Now that I think of it, I can remember 3 instances of LeMay in alternate history and all 3 make him look pretty good. One is in a Cuban missle Crisis gone hot where people suspect him of going over his station, but turns out it's a soviet fail-deadly plan of payback setting stuff up on the USA to lead to a rebelion and LeMay shows up pissed to a white house under siege to report to JFK that he is there to follow his orders and bomb the rebels into smithereens. Secon was one old TL on this site where the west does fall to commie revolutions like the USSR "predicted" and LeMay is the last US president (having been Wallace VP and getting the job after he is shot). He contemplates ordering a strike against the USSR for the domestic problems with Civil Rights and protests and such, but decides against it and instead announces he will step down from the Raven Rock bunker (after which a Social Democrat - Socialist - Commie USA is born, though I don't quite remember).

And the 3rd is from The New Order where he again becomes president after Wallace is shot, but in this case he actually goes and forces Civil Rights and a end to segregation via presidential decree to the absolute complete anger of most of his allies in government. A event shows him signing it not out of any love of the plight of minorities, but because he figures the USA needs to move on from segregation to go forward and he can do it, and since he never wantes to be POTUS and has no plan to run again he os happy to put a torch to it all at be the guy that does what has to be done and hated for it.
 
Evan Mecham, perhaps? He was so racist and corrupt during his brief tenure as governor of Arizona that he was impeached and recalled at the same time.​

He was also convicted of a felony at the same time. There were three methods a Arizona governor could be removed from office at the time. Recall, impeachment, and criminal conviction of a felony. To my knowledge he's the only politician in US history to have all three happen simultaneously on the same day.

One of his nutter accomplishments as Gov was appointing an ex bank robber to be in charge of prisons and an illiterate man to be in charge of education.
 

marktaha

Banned
He was also convicted of a felony at the same time. There were three methods a Arizona governor could be removed from office at the time. Recall, impeachment, and criminal conviction of a felony. To my knowledge he's the only politician in US history to have all three happen simultaneously on the same day.

One of his nutter accomplishments as Gov was appointing an ex bank robber to be in charge of prisons and an illiterate man to be in charge of education.
Well the first would at least have had some practical knowledge!
 
To follow the Quadros example, maybe have Agnew be elected following Watergate (also assuming he doesn't become Nixon's initial VP) on a wave of anti establishment backlask
 
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