One Bet That Norm MacDonald Should Have Made

Norm MacDonaldEveryone knows that the late, great Norm MacDonald was one of the sharpest comedians out there. Some people know that he loved to gamble – and routinely did it to the point of recklessness.

Fans remember that he sometimes combined gambling with comedy, as is evidenced by one of my favorite Norm jokes: “People know I go to Las Vegas a lot and they always ask if I saw the white tigers at the Mirage. I say, ‘Only if they were sitting at the Let It Ride table.’”

I got to spend a fair bit of time hanging out with Norm and once wrote about a weekend of breakneck gambling with him in Las Vegas. It was originally penned for Playboy, which killed the piece because Norm “did not live up to the Playboy lifestyle.”

In other words, weeks before Playboy would be opening a nightclub and casino at the Palms, its executives didn’t want to run a story about a guy burning through $40,000 in less than 48 hours at the Mirage.

Fair enough. After Norm’s death in 2021, I sold it to GQ.

What most people don’t know about Norm is that he was smart as hell. You could pull a card out of a deck and he would quickly sort through the remaining 51 and tell you which card you have. That’s impressive.

He was also a dynamite Scrabble player. I’m pretty good and he routinely crushed me. When the show “Who Wants to be a Millionaire” was big, they regularly did episodes in which celebrities played for charity.

Norm was on there in 2000. He intentionally manipulated things so that he was the last of some half-dozen celebs to appear – never mind that it meant making himself look like he was too dumb to beat the others in a preliminary round.

“I wanted to do it when no celebrities were left,” he told me. “They were all shouting answers to one another. I wanted to play the game straight up. I wanted to hit the million-dollar first prize on my own.”

Playing for the Hole in the Wall Gang Camp, Paul Newman’s charity that benefits kids with serious illnesses, Norm was off to a firecracker of a start. He got up to $32,000 without breaking a sweat.

Then came a commercial break. Backstage, fielding cell-phone calls from his bookie, he made large bets, adjusted the wagers and might have been making his beloved lighting bets. They’re particularly volatile – as wins or losses can go through the roof, based on an over/under bet – and embraced by the most degenerate of gamblers.

Show-host Regis Philbin heard all this going on and, according to Norm, he was rattled.

Soon after, Norm quickly burned through two of his lifelines.

Regis asked, “How are you going to win a million dollars?”

“I’m not now,” Norm said with a laugh. “That dream is as good as dead.”

The third was consumed as he hit the $250,000 mark.

During ensuing breaks, Norm amped up his conversations with bookies.

Then he faced the $500,000 question, which involved a Broadway show. Norm smirkingly insisted, “I’m not gay, so I don’t know much about Broadway musicals.”

Regis suggested that maybe he should take the money and run. Clearly he did not want hard-gambling Norm to wildly risk $250,000 – especially when Norm played dumb – maintaining his belief that the X-rated musical “Oh, Calcutta” was
set in India.

He hit 500K and faced the $1 million question: During the Cold War, the U.S. government built a bunker to house Congress under what golf resort?

The correct answer was the Greenbrier – I knew that one because it was the subject of a recent “60 Minutes” report – and Norm contemplated logging it.

As Norm mulled, Regis sounded as if he had been influenced by what we saw backstage.

“You’ve got a little gambling streak in you, don’t you?” Regis asked. “You want to see if you can beat the game, don’t you?”

Getting the question wrong would have taken $468,000 away from Newman’s charity (no matter what, $32,000 remained in place). Norm said he thought it was Greenbrier.

He was about to put that in as his final answer.

Then Regis implored, “I’m not kidding. Unless you’re sure… [do you want to risk] $468,000?”

Norm wanted to risk it. He always wanted to risk it. But Regis spooked him.

Thinking he had a poker-style read on the show host, Norm decided to walk with the $500,000.

Game over, Regis asked what his answer would have been.

Norm replied that it would have been Greenbrier.

Regis exclaimed, “You would have won a million dollars!”

Norm’s body contorted in the reaction of every gambler who blows a sure thing.

Years later, Norm told me, “Regis thought I was a crazy gambler and talked me out of going for the million. I wanted to get there so badly. I wanted to be on stage with all the confetti coming down.”

He didn’t mourn not winning the money. Of course, it was the other thing. As Regis suspected, like all dyed-in-the-wool gamblers, Norm wanted to beat the game. Simple as that. And, had he not made the out-of-character move of putting on the brakes, he would have.

Michael Kaplan

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.