Losers in Brief: The Federalist Follies

(part 1 of 12)

Since 1789, 112 men have won at least one electoral vote. Of that group, 65 never became President or Vice President. Of them, 30 were a bunch of ambitious losers who tried for the most powerful office in the country and failed. These are their stories.

Charles Cotesworth “C.C.” Pinckney (Constitutional Delegate, Federalist-SC) Lost to Jefferson-1800, 1804; Madison-1808

On the list of Founding Fathers you’ve never heard of, Pinckney ranks pretty darned high. He was a Brigadier General in the Revolutionary War, Delegate to the Constitutional Convention, and Foreign Ambassador. He was so fucking loved amongst the Founders, that when Washington offered him a choice between Secretary of State or Secretary of War, he picked neither. Badass!

So why’d he lose? He basically chose the wrong side of every issue. At the Convention, he was against abolishing slavery, and he was for senators being unpaid rich people that were just sort of trusted to do the right thing. What the fuck? He was the poster child for Federalism, and I think the party had a meltdown when he decided to stop running.

DeWitt Clinton (Lt. Governor, Federalist-NY) Lost to Madison-1812

Had the election been held in just the state of New York, Clinton probably would have won and made all his opponents cry. Seriously, he was State Senator, U.S. Senator, Lt. Governor, Governor, Mayor of NYC, and delegate to the state’s Constitutional Convention. Did I mention he ran in those elections with no less than three different political parties? Only in America could the Grand Master of the New York Freemasons lose to a guy half his height.

So why’d he lose? The War of 1812. Incumbents never lose during a war. (He faired better than any Federalist since Adams, so that’s something.) Maybe if he had built the Erie Canal against heavy opposition before the election, he’d have won. Oh, I didn’t say that before? Yeah, he built the fucking Erie Canal.

Rufus King (Diplomat, Federalist-NY) Lost to Monroe-1816

After helping to draft the Constitution, King served as one of the first Senators from New York. Washington appointed him Minister to Britain, a position he held with much success under three presidents, including Jefferson, who hated Federalists with an intense passion. He was so good that relations between the U.S. and Britain fell apart without him.

So why’d he lose? The question should really be, “Why the shit did he run?” The Federalist Party was dead at this point, and he did so poorly in the election that Monroe ran unopposed next go round. He didn’t even win New York. It’s a shame, though. He was staunchly anti-slavery, and if he were President during the Missouri Compromise, he might have been able to curb the slave trade.

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