Most likeliest POTUS possible to be the most pro-Axis?

I doubt he'd be re-elected with such a policy in 1940. Even though the american public didn't want to join the war, they wanted to support the British.
 
Henry Ford
In industrialist who knows how to build industry, elect Ford to rebuild American industry
He was still somewhat of a folk hero and an anti-semite if he chose to run he might have been able to do it
By 1940 Henry Ford was regarded by many as a fool. He had a famous libel suit against the Chicago Tribune in the 1920s when he showed himself to be ignorant of most basic American history and current events. Among other things he said the American Revolution was fought in 1812 and that Benedict Arnold was a writer. He claimed he had only voted once for President and that vote was for James Garfield. The Tribune's lawyer quickly pointed out that Ford was only 17 years old in 1880 and could not legally have voted for anyone. His attempt to produce rubber in Brazil was an expensive failure. I don't think Ford could have been elected.
 
Possibly, but how likely was that?
Avoid the murder of the Lindbergh Baby and the associated media circus, and it gets more likely. Lindbergh's wife was an ambassador's daughter. His father was a congressman. Lindbergh himself already flirted with organized politics in the Air Mail scandal. Lindbergh as a Republican nominee in 1936 or 1940 is a lot more likely if he spends the years between 1935 and 1940 in the US.
 
Joseph P. Kennedy Sr. .... has the necessary connections, did his bit to support Hitler by attempting to convincce FDR that the British were a lost cause (and, it has been suggested, might well have deliberatly leaked information with indescreet talk at embassy parties ..)
 
Senator Gerald Nye (R-ND) was one of the leading isolationists in Congress. He may not have been a likely presidential candidate, but if elected president, he would maintain neutrality with Nazi Germany and focus entirely on an "America First" (i.e. America Only) foreign policy, letting the Nazis rampage across Europe so long as they didn't attack the Americas. He was a demagogue who alleged that a conspiracy of munitions makers had brought the U.S. into World War I, and he accused Hollywood of agitating for the U.S. to enter WWII on the side of the British. He also flirted with antisemitism by accusing Jews of controlling Hollywood. If you want a president who would turn a blind eye to Nazi aggression, then Nye's your guy.
 
Joseph P. Kennedy Sr. .... has the necessary connections, did his bit to support Hitler by attempting to convincce FDR that the British were a lost cause (and, it has been suggested, might well have deliberatly leaked information with indescreet talk at embassy parties ..)
Getting JPK Sr. elected President is more-less implausible. His being an Irish Catholic itself is going to destroy any chances; it killed Smith's Presidential ambitions, leading to (until then) the worst electoral disaster the party had ever faced. And it hurt his son in 1960, especially in the South, West, and border states. But Kennedy has even more problems: he's a leading opponent of American involvement into the war, making him anathema to New Dealers and FDR, even if Kennedy's views were based less on sympathy of Germany and more on the traditional Irish-American dislike of England. The traditional Democratic establishment -- Garner, Smith, etc. -- had lost power by this time, and I'm not so sure they were going to be trustful of Kennedy, the ex-chairman of the Securities & Exchange Commission. Lastly, his business career isn't going to gain him any friends amongst Western progressives (the guys who supported McAdoo in 1924 and FDR in 1932). Yes, he could become VP first...but FDR never really thought much of him, and could have easily blocked his selection as running mate.
 

McPherson

Banned
Another route is to not have Roosevelt influenced by the early Warhawks. Before 1938 he had dialed down the Banana wars to a effective end. Slowly reduced US intervention in China, and taken action on the long postponed independence of the Philippines. Have isolationists counter the persuasion of the US opponents of the nazi regime & early warhawks in 1938 & Rosevelt may not work with Churchill & the French leaders 1938-1941 to dra the US towards active support. No rewrite of the Neutrality Acts in 1939, no two Ocean Navy Act. No aggressive military mobilization of 940 in the panic after France collapsed. A less aggressive Neutrality Zone in the Atlantic, and most important no embargo acts aimed at destroying Japans economy.
Roosevelt had too many domestic problems in 1938 remaining to go off hankering for Wilsonism. Nevertheless, ever since his meeting with Schact in 1934 and the German repudiation of their financial agreements with the United States, and his previous experience with the Germans as part of the Wilson administration, itself, FDR was most decidedly out to get Hitler, any way he reasonably could. He had a visceral hate for that man and his criminal regime.

The FDR policies with regard to the Philippine Islands and the French and the British in east Asia and with China in the later 1930s was a mix of REALPOLITIK and anti-colonialism. FDR did not think the US geo-politically could afford a war to settle the Pacific with Japan and he was well aware of what Wilson's political damage to the US had resulted when that evil man took the Americans into a world war a generation earlier.
 
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