Kaycee McIntosh and Julie Henningsen recount the June 2008 Regatta de Amigos disaster in the Gulf of Mexico, when the 38-foot racing sailboat Cynthia Woods lost its keel, punched a hole in the hull, and capsized in 30–60 seconds about 11 miles south of Matagorda. Safety officer Roger Stone woke to rising water, warned the crew, and pushed two sleeping sailors up through the flooding companionway, but never surfaced; five others survived by lashing together, keeping a positive mindset, and signaling with a single flashlight until the Coast Guard rescued them 26 hours later, while their EPIRB and life raft were trapped below deck. The episode highlights wearing life jackets early, carrying a waterproof light, having a float plan, and mounting EPIRBs for automatic access, then covers conflicting investigations, a settlement supporting Stone’s children, and his posthumous Coast Guard Gold Lifesaving Medal.
00:00 Podcast Intro
00:29 Nightmare Below Deck
02:49 Meet the Crew
07:23 Rough Night Conditions
10:42 Keel Failure Chaos
15:23 Escape Into Darkness
17:17 Staying Alive Together
19:46 No Beacon No Raft
21:46 Needle in Haystack Rescue
25:05 Recovery and Loss
25:31 Safety Lessons Offshore
29:24 Investigations and Lawsuit
33:44 Honoring Roger Stone
36:07 Final Takeaways and Outro

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