Transcribed

Confessions of a Crossroader

Nov 9, 2026 · 55m 21s
Confessions of a Crossroader
Description

Sid Wyman — Life is a Gamble Guest: Sid Wyman — pool player, golf gambler, poker player, and what they used to call a rounder (or cross-roader). Show Notes 00:00...

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Sid Wyman — Life is a Gamble

Guest: Sid Wyman — pool player, golf gambler, poker player, and what they used to call a rounder (or cross-roader).

Show Notes
00:00 Growing the show — please subscribe and review
02:45 Meet Sid Wyman: pool player, golf gambler, rounder
03:54 Fort Smith kid: the bookie umpire and the CB radio
05:24 Bought a new Cadillac the day he turned 16
08:56 Chauffeur for Big Eddie Glantz in Oklahoma City
12:44 Meeting Bobby Baldwin
14:33 The Vegas golf crew: Puggy Pearson and company
17:40 Fifty dollars to Vegas, hustling pool along the way
18:24 The daub: marked cards at the Lady Luck
21:30 Courtroom: the case thrown out, the pencil snaps
23:36 The bomb: beating the Barbary Coast for $600,000
30:38 Oklahoma tribal casino: five straight wins, banned for life
34:02 Mr. Casino Honesty
37:55 Corporate security asks him to corrupt two dealers
40:00 Wife of 35 years
41:17 Cheating in poker today: turn the Wi-Fi off
46:06 Strippers: how marked decks are made
49:43 Hustler Casino: she wasn't cheating
51:07 Billy Baxter, the smartest gambler he knows
54:50 Wrap-up
Life is a gamble explores those times in life where someone must take a big risk, or when life deals you am unexpected hand.  How do we decide how much risk is worth it?
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Information
Author Gambling With an Edge
Organization Richard W. Munchkin
Website -
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