Would the GOP have done better with a more experienced candidate than Willkie in 1940?

[Sabin]

My second esoteric history nerd fact: if you watch any C-SPAN show where Thomas Dewey Jr is a guest, it is the most awkwardly passive aggressive (on his part) thing you will ever see. They try to talk to him about his father and his governorship and 1948, and he has absolutely nothing to say. He gets clearly annoyed (then why agree to be interviewed?) and the historians are desperate to get blood from a stone and are trying so hard to make up for his slack and make it not awkward. Google it and I swear you'll agree.

I remember seeing that on the series THE CONTENDERS. Amazingly hostile.

 

[dmg86]

It also didn't help Teddy Roosevelt that Eleanor went around New York in a car with a teapot on it. Something that caused a rift in the family and for which she apologized for later.

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[Amadeus]

What if Dewey had won his 1938 gubernatorial run?

In that case he'd be a much more serious contender. He's the Governor of the most populous state in the Union, albeit at only 38 years old. I suppose Roosevelt could respond to Dewey by calling him, "the boy Governor." After a loss in 1940 Dewey most likely sits out 1944 and runs again in 1948 only to lose again as he did IOTL.