The Legend of Amarillo Slim

This is from 2003 on Weekend Edition Saturday:

Amarillo Slim Preston has been called the greatest gambler who ever lived. He's won bets not only in pool halls and poker games, but golf courses, rivers and jail cells. But Preston, who first rose to national prominence when he won the World Series of Poker in 1972, insists that he's not a compulsive gambler. He's a professional.
"In my humble opinion, I'm no ordinary hustler," he writes in the introduction to his newly published memoirs. "You see, neighbor, I never go looking for a sucker. I look for a champion and make a sucker out of him."
In Amarillo Slim in a World Full of Fat People, the consummate gambler relives some of his greatest exploits. Among his famous victims are country music legend Willie Nelson ($300,000 playing dominoes) and adult magazine publisher Larry Flynt ($2 million in a poker game). In a recent interview for Weekend Edition Saturday, Preston tells NPR's Scott Simon that the trick to winning lies in knowing the odds.
"When you put down a sports wager," he says, "it helps to know something other people don't know."
It's a principle he's put to use in creative ways. In the 1970s, for example, Preston challenged former Wimbledon champion Bobby Riggs to a high stakes game of pingpong, insisting only that he be allowed to choose the paddles. Riggs agreed — and was soundly beaten when Preston showed up with two cooking skillets (which the gambler had been secretly practicing with for months).
Now in his mid-70s, Preston is still active in his trade. He's spent the last few weeks playing in the World Series of Poker in Las Vegas — and he's still a winner. Recently, Preston bet that golf star Annika Sorenstam, the first woman to play in a PGA Tour event in 58 years, would not make the cut at the Colonial tournament. Once again, he was right.

It is worth listening to the piece.  It is really funny.