This isn't a horse racing story, but it's a gambling degeneracy story.
When I was in my late teens and early twenties I spent a lot of time in a Queens poolroom that was full of terrific pool players, a lot of gamblers, and quite a few degenerates.
Occasionally, the pool gambling would spill over into other forms of gambling.
"Big" Steve was pro level 9 ball player and well known degenerate gambler around NY and NJ and even on the road.
"Crazy" Randy was more of mid level player, but all around degenerate and CRAZY.
They didn't like each other at all.
One day "Crazy" Randy offered Steve 6/5 on coin flips.
Steve verified that the coin was legit and accepted.
I can't remember the exact amount, but Randy got hot and busted Steve for his entire bankroll despite giving him odds. Steve was fuming and Randy was gloating.
Randy then offered Steve "double or nothing on the pool cue".
A totally broke pool hustler with no cue is a problem, but Steve had to accept because he was in the hole for a lot more than the cue was worth.
They flipped and Randy won again. The place went nuts.
Then Randy offered him double or nothing on his shirt. Yes, all the money, and the pool cue against Steve's shirt. Steve accepted.
Randy won again. Steve took his shirt off and handed it to Randy. Randy went outside, smashed the cue into a dozen pieces (this was a very good cue) and set Steve's shirt on fire.
It's hard to be more insane than that.
