History & culturePody PodTeddy Roosevelt one Wild AF President | Shane Gillis & Louis Ck History

Teddy Roosevelt one Wild AF President | Shane Gillis & Louis Ck History

Long-form19:02People & BlogsPublished May 5, 2026, 12:46 AM · 5mo ago
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Description

#mssp #comedy #history #shanegillis #mattmccusker #podcast Theodore Roosevelt was, by any measure, the wildest human being ever to occupy the White House. Born sickly and given a death sentence in his teens, he willed himself into one of the most physically and intellectually relentless figures in American history — climbing the Matterhorn, charging up San Juan Hill, breaking up monopolies, founding the National Park System, getting shot mid-speech and finishing the speech anyway, and exploring an uncharted Amazon tributary at age 55. In this episode, Louis CK, Shane Gillis, and Matt McCusker walk through the chaos of the McKinley-to-Roosevelt transition and the absurd, brilliant, terrifying presidency that followed. From the USS Maine and the yellow-journalism war with Spain, to the origin of the teddy bear, to the night TR hosted Booker T. Washington at the White House and the entire U.S. Senate lost its mind, to the (probably apocryphal but too good not to tell) story of him bare-knuckle boxing the heavyweight champ in the Oval Office. A look at the man, the myth, and the sheer kinetic energy of America's most unhinged president. Chapters 00:00 The Gilded Age depression and the rise of McKinley 00:50 The Spanish-American War and the USS Maine 01:50 Teddy's sickly childhood and "make your body" 02:30 The caricature king of American politics 03:00 Reforming the NYPD and inventing the police academy 04:30 The Sunday drinking crackdown 05:00 Montana, the Navy, and the War of 1812 obsession 06:00 Inventing the National Park System 06:40 The Rough Riders and San Juan Hill 07:50 Oyster Bay, family, and the Roosevelt brothers 08:50 Elliott Roosevelt's tragic decline 09:30 Where teddy bears actually come from 10:50 McKinley's assassination, Teddy takes the office 12:00 Dinner with Booker T. Washington 13:00 Charging the hill (and getting people killed doing it) 13:50 Boxing the heavyweight champion 15:00 Trust-busting and presidential ambition 16:10 First president to fly in an airplane 16:50 The Bull Moose run and getting shot mid-speech 18:10 Taft, the bathtub, and Wilson takes over

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