The Modern Meeting

Ep. 98 - Louis Ruggiero: Everything to Lose — And He Did (Part 1)

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0:00 | 1:12:18

Louis Ruggiero grew up on the Upper East Side of Manhattan. Private school. Three sports. By most measures, he had every advantage. At 14 — he turned $200 into $9,000 at a blackjack table in the Bahamas and lost every penny before checkout. By 21 he had a bookie, three felonies, and was stealing checks from a friend to stay in action and fund his other addictions. 

This is Part 1 of a two-part conversation. Louis walks us through the early years — the entitlement, the structure that kept him together in high school and collapsed the moment he left for college, and the first real consequences that came when charm and a well-connected family couldn't bail him out anymore. 


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