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74: Con Me Once pt.2: Winners and Losers

Updated: Aug 5


An episode unlike any we’ve done before! Grant dives into the legacy of “NSA leaker” Reality Winner, revealing a story far more complicated and nuanced than the headlines ever suggested. Along the way, we wrestle with tough questions about patriotism, transparency, and what real service to the country looks like. You’ll even hear Reality’s own words, lifted straight from the candid emails she sent our inbox, so the saga unfolds in her voice, not just ours. Whether you’re a policy junkie, a true-crime buff, or simply love an underdog tale, you’ll leave with fresh angles. Grab your headphones, bring a curious mind, and let’s untangle the myths, the media spin, and the human being behind one of the decade’s most polarizing headlines. Find out what makes this women, and this episode, so truly special. Winners and Losers—out now!

 

Chapters/Key takeaways to listen for

  • [00:00:00] Catch-Up: Grant & Maia pop beers, talk Huskers, buffalo chicken, and why recording on a Saturday is chaos

  • [00:07:30] Scooter Wipe-out Comedy: Maya helps a stranger who crashes a seat-scooter, gets a “her-she” chocolate pun, and Grant loses it

  • [00:16:00] Hot-Girl Walks & Bagels: Grant recounts chaperoning 22 students through Times Square, Lydia’s magical blueberry bagel, and the art of being “babied”

  • [00:24:20] Winners and Losers

  • [00:38:40] Cry-Run CrossFit: How Reality dealt with trauma 

  • [00:55:10] Journalistic Face-plant: The Intercept shows the doc to NSA & FBI, exposes printer dots & creases—Feds trace Reality in hours

  • [01:03:25] Charged under the Espionage Act: Comparison to Thomas Drake, Diane Roark and why “following proper channels” fails whistle-blowers

  • [01:24:30] COVID Behind Bars: Transfer to Texas; 500 women positive; what “double-ass jail time” feels like

  • [01:30:45] Post-release life: CrossFit shed by the pasture, petting her horse between sets “My life is perfect right now”

  • [01:36:20] Hollywood Portrayals: Reality on being played by Sydney Sweeney & Amelia Jones, eating-disorder triggers, and the male gaze

  • [01:43:00] Winners vs. Actual Spies: Reality vs. Maria Butina vs. Anna Chapman vs. Trump’s Mar-a-Lago docs

  • [01:55:40] Patriotism Reframed: Grant’s thesis: real love of country means challenging it; Maia cries in the podcast “club”

  • [02:08:30] Listener Letters & Tears: Closing emails, gratitude, and the episode’s emotional mic-drop


Quotes:

  • "To be a true patriot of your country, oftentimes means you have to be adversarial of it." - Grant Thomas 

  • "The government is democratically elected that we allow the government to hold secrets because it is still responsible to us as the people." - Grant Thomas 

  • "Peacemaking is less of a rational economic model of dividing resources and territory fairly." - Grant Thomas

  • "You should only be denying bail to people who have a proven record of being too dangerous to be out there." - Maia Warner 


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Sources:

“Reality” directed by Tina Satter from a screenplay by Satter and James Paul Dallas 

“Winner” directed by Susanna Fogel and written by Kerry Howley


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