Riding to the Badlands with Teddy Roosevelt | Ed O’Keefe

Mike and Grubes kick off December with a lightning strike, a World Series flashback, and the age-old question: are we even gonna make it to (and through) Christmas? Then they welcome a very different kind of guest into the YDC mothership: Ed O’Keefe, CEO of the Theodore Roosevelt Presidential Library Foundation.
Ed takes the guys from Grand Forks to the Badlands, explaining why Teddy Roosevelt’s story is so insane it would get rejected as fiction: a sickly bookworm who becomes a cowboy, Rough Rider, president, and the original “media-savvy” politician. They dig into the brutal day his wife and mother died in the same house, how the North Dakota Badlands literally saved his life, and why his ranch became the “cradle of conservation.”
Along the way, Ed talks about inventing modern social video at NowThis, working with Anthony Bourdain, and how TR used newspapers the way modern politicians use social media. They get into Rough Riders lore, Teddy’s ties to Texas, trust-busting showdowns with J.P. Morgan, cocaine as a legit medical treatment back then (to the delight of Grubes), and why the new presidential library will feature an AI Teddy, a horse hitch, a living roof, and virtual campfires in the Badlands.
If you like presidents with actual side quests, history that weirdly mirrors right now, or the idea of riding a horse to a presidential library, this one’s your episode.
Chapters
00:00 – Lightning Strike & Cold Open Chaos
01:08 – Will We Even Make (and Clear) Christmas?
01:38 – Meet Ed O’Keefe & the TR Library
03:01 – Fast Eddie, Ed, or Edward?
03:53 – Growing Up in North Dakota (a.k.a. Almost Canada)
06:13 – Fargo, the Movie Curse & The Accent Question
07:13 – What Even Is a Presidential Library?
08:20 – Turning a Library into an Experience (Horses Welcome)
09:11 – From ABC News to NowThis to CNN
11:26 – Working with Anthony Bourdain
14:05 – Why Teddy Roosevelt’s Life Sounds Made Up
17:15 – The Day His Wife and Mother Died
18:37 – “The Light Has Gone Out of My Life”
21:43 – Badlands 101: Hell with the Fires Out
23:30 – Cradle of Conservation: Elkhorn Ranch
25:29 – Why TR’s America Feels a Lot Like Today
27:00 – Teddy Roosevelt Comes to Texas
28:44 – Who Were the Rough Riders, Really?
30:18 – From Assistant Navy Secretary to President in Three Years
31:48 – Was He Actually Popular? (Short Answer: Yes)
32:16 – Mastering the Media of His Time
35:22 – Tech Shifts, Immigration Waves & Familiar Fights
36:12 – Mid-Show: CBD House of Healing
38:49 – Mid-Show: GivingMas at the Barley House
41:00 – “Speak Softly” & Modern Political Communicators
43:45 – Party Chaos, Third Parties & 1912 Mayhem
46:07 – JP Morgan vs. Teddy: Trust Busting & Respect
48:36 – Weekends, Worker Safety & Cocaine as Medicine
50:54 – Opening Date & How to Get in the Arena
51:50 – AI Teddy, Virtual Campfires & the TR Triangle
53:30 – YDC Road Trip to Medora
53:45 – Outro, Shoutouts & “Drop Us In Anywhere”
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Follow Your Dark Companion on Patreon for every episode:
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To reach out email us at: Info@Stolenwatermedia.com