Winning at Losing

A history podcast about failure, telling the stories of people who ran for President of the United States and lost.

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Episodes

Trailer

Sunday Oct 22, 2023

Sunday Oct 22, 2023

History by the losers. Each episode explores the life of someone who ran for President of the United States and lost. Within these stories of the past, discover a key insight for the present: how to win at losing.

Episode 1: Daniel Webster

Tuesday Nov 07, 2023

Tuesday Nov 07, 2023

What's it like to try, try, and try again... only to fail, fail, and fail again? Daniel Webster was many things - lawyer, politician, legendary orator. But despite multiple attempts, he never won the office he prized: the US Presidency.

Episode 2: James G. Birney

Tuesday Nov 14, 2023

Tuesday Nov 14, 2023

What's it like to lose... on purpose? James G. Birney ran for president twice. He lost twice. But this was the plan, because for him, winning wasn't the most important thing. What was?

Tuesday Nov 21, 2023

What's it like when Destiny sets you up to fail? John C. Breckinridge was adored so much, he won a presidential nomination... at the worst possible time. No wonder he didn't want it.

Episode 4: Horace Greeley

Tuesday Nov 28, 2023

Tuesday Nov 28, 2023

What's it like to believe you have all the right answers, and then one day realize how wrong you were? Horace Greeley ran for president to fix a broken country. He wasn't prepared to fail so publicly.

Episode 5: Victoria Woodhull

Tuesday Dec 05, 2023

Tuesday Dec 05, 2023

What's it like to be silenced? When fighting back against her critics, Victoria Woodhull - the first woman to run for president - wasn't shy. Today her story often goes untold. Did her critics win in the end?

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Winning at Losing is the only presidential election history podcast devoted to the underdogs. If you’ve ever felt the sting of failure, then you’ll find some motivation and inspiration in these stories of some of American history’s biggest losers.

 

Host David Sadzin tries to overcome his own feelings of inadequacy while guiding you through these fascinating, strange, sometimes-heartbreaking, occasionally-humorous stories of political failure and defeat. 

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