when the GOP first nominated an outsider

The New York Times has a useful story by presidential historian Michael Beschloss reminding us of the first  time the Republican party nominated a business executive as its presidential candidate. In 1940, the GOP chose Wendell Willkie, head of an electrical utilities holding company, over established politicians like Robert Taft and Thomas Dewey. It was even more surprising that Willkie had been a registered Democrat until 1939. But he had the internationalist, northeast wing of the party behind him, denying the isolationists a choice in the election.

I think it was good for America that Willkie did not oppose FDR's destroyer-for-bases deal with Britain or the first peacetime draft.  As Beschloss notes, Willkie did stress isolationist themes late in the campaign, but FDR trumped them with his own disingenuous promise not to "send our boys into any foreign war." FDR won handily but then welcomed Willkie as a statesman.

Beschloss mentions that Willkie had a mistress but fails to note that, for part of the campaign, she campaigned at his side. But the press made nothing of the fact, just as it failed to report FDR's disability. That was then, of course. Impossible to imagine now.