Presidential Losers since 1900 by PolinskyL

What losing candidate reached only the rank of Captain before moving into politics, perhaps disappointing his father and grandfather, who were both four-star Admirals?

What man, who did not receive a majority of the electoral college vote, began his political career by quitting law school to run for Congress? (He had earlier quit journalism to start law school, and would eventually quit his House seat for a Senate seat.)

Ted Cruz has tried to make hay of Donald Trump's past support of Democrats. What Republican switched party affiliation shortly before running, even having been a delegate at the Democratic convention just eight years earlier?

Two 20th-century losing candidates would go on to be the named partners in large 'white-shoe' corporate law firms. Name one of the 3 law firms which carried one of those candidates' names.
Name the LAWFIRM, not the candidate.

In what candidate's lucrative pre-political professional career was he a colleague of a man who would later become the Prime Minister of Israel?

Two consecutive losing Democratic nominees were born in the same lightly-populated state, though one of them was generally associated with a neighboring state. Name both men.

What man quit the Supreme Court to become his party's nominee? Although he lost the election, he did eventually get to be Secretary of State, and would later get reappointed to the Court as Chief Justice.

5 different major-party candidates have lost a Presidential election to a Roosevelt. Who was the first?

What candidate ran the Boston Marathon as a 17-year-old high school senior at Brookline High School?

Two men who simultaneously held statewide elective office in Illinois were both renowned for their rather differing speaking styles. One, a prominent senator, was called (presumably not by his friends) "The Wizard of Ooze." Who was the other man, more self-deprecating in style, who lost two presidential elections?

What future senator is being described here? 'When fellow soldiers saw the extent of his injuries, all they thought they could do was to "give him the largest dose of morphine they dared and write an 'M' for 'morphine' on his forehead in his own blood, so that nobody else who found him would give him a second, fatal dose."'?

Two losing candidates (one from each party), 8 years apart, shared a 6-letter first name, though both went by (different) shorter forms of said name. Name both.