This wasn't a huge flip in the grand scheme. It was nice seeing people in action without requiring a background investigation of every match they ever played.
When I was 17, one of the Pro Events came through an area local to me...I don't want to give out too many details-- this is early 90s. One guy, who apparently was a professional gambler (Golf, Pool, Everything) was sitting in the stands next to his "security" man (bodyguard) when a young man came up to him and said, "I've found someone to flip with you!" I happened to be sitting next to him and his partner. An older guy, in blue jean coveralls came over and pulled a knot of hundreds out of his chest pocket that would choke a horse. "$1000 a flip?" he asked. "Sure!" replied Pro Gambler. Coveralls beat gambler out of a QUICK $15,000 (something around that range...this was 25 years ago or so), which was all Gambler had in his pocket at that moment. Gambler, in good spirits, sent his bodyguard on and said aloud, "I'm sending him to get $100K more." I never saw them flipping again, but I did see the Gambler in various action matches throughout the remainder of the event.