Winners & Losers: Losing $40,000 with Norm MacDonald

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Norm Macdonald is a hard guy to forget. He was a particularly hilarious comedian with the best gambling stories.

Like the time when, as a burgeoning stand-up in Los Angeles, he took his mother and aunt to Las Vegas and lost all his money before they even got to the room.

It was made all the more tragic because he bet the last of his cash on a blackjack hand, got dealt two aces and could not afford to split. So he hit twice, landed one 10 after the other and lost the bet instead of winning twice.

I thought of him because he died in the month of September, which was when I filed my previous column. And its title was ‘Playing the Don’t’.

$40,000 Down the Toilet

Norm and I did a story once, where the plan was for him to put at risk all the money he was paid for a stand-up gig at the House of Blues in Mandalay Bay.

It totaled $40,000 and the idea was to double it or lose it all, as I told GQ in an article after his death. He began by playing the “don’t” at craps – claiming that it was a no-fail approach he called his ‘pensioner’s system’.

  • Playing the don’t is betting for the house to win and for players to lose.
  • It’s a good way to make everyone at the table hate you.
  • Essentially, you’re rooting against them and rooting for the casino.

But the table was so hot, and everyone was winning so much money, that nobody cared about Norm’s don’t-y ways.

But the table’s hot streak continued and Norm began flushing the purple chips down the toilet. And, after a woman at the table recognized Norm and kissed him on the cheek, he told me about something he hated.

Norm said the worst thing about being a celebrity in a real money casino is losing small fortunes and having people insist that it doesn’t matter because you’re rich and famous.

Even if you’re rich, he said, not insinuating that he was rich (though he was surely better off than me – and often picked up tabs), you still hate losing money to the casinos.

Of course, through the don’t, reckless blackjack play and an unlucky NBA bet, Norm lost it all.

Loaning Norm MacDonald Gambling Money

On a losing streak, Norm asked to borrow $10,000 from me. I grudgingly loaned him a grand.

He said that my turning him down for the larger sum put him on tilt and that it contributed to him vaporizing my money in what felt like seconds (but was probably minutes).

Meanwhile, I was gambling like an actual pensioner, playing in a slow $1/$2 limit hold’em game as Norm impatiently sweated me. He wanted to go for a sushi lunch and get out of town.

A few weeks later, Norm may or may not have contributed to my daughter getting into a good pre-K program. Public schools in NYC are screwy; the year before kindergarten is not guaranteed and the getting-in process is a hustle for parents.

Norm Repays the Favor

Norm and I were both at the World Series of Poker, which was still being held at the old Binion’s Horseshoe.

  • There was a media tournament, free to enter with a $10,000 first prize that had to be donated to charity.
  • Though not exactly media, Norm was enough of a celebrity to be invited to play.
  • Deep into gambling, he could not take seriously a game with nothing to lose and nothing materially to win.

We were sitting next to one another, I got dealt a monster hand and raised. He shoved and of course, I called.

Excited, I quickly, prematurely, flipped up my cards to show a full house. He spacily mucked, half smiled and headed off for the nearest craps table.

Winning $10,000 with Norm’s Help

Somebody in the game accused him of chip dumping. I don’t think he even heard the guy.

Whether Norm did or didn’t, winning that hand set me up to get home in the tournament. I won the 10K for charity, contacted the school and offered to give them the money if they let my daughter in.

They did! I was awarded a giant check and toted it around proudly. Norm saw the check and said, “That’s like winning a giant panda at the carnival.

“It seems cool as long as you are at the carnival. But the further away you get, the more of an idiot you feel like for carrying the giant panda.”

Norm, who won $500,000 on Celebrity Who Wants To Be Millionaire, was right. I ditched the giant check in an airport trashcan before boarding my flight and heading home.

Michael Kaplan
Gambling Author and Journalist
Michael Kaplan
Gambling Author and Journalist

Michael Kaplan is a journalist based in New York City joined Techopedia in November 2023. He is the author of five books ("The Advantage Players" comes out in 2024) and has worked for publications that include Wired, GQ and the New York Post. He has written extensively on technology, gambling and business — with a particular interest in spots where all three intersect. His article on Kelly "Baccarat Machine" Sun and Phil Ivey is in development as a feature film.