By Tim Dahlberg

LAS VEGAS (AP) — Before 42–1, there was 27–1.

That was the number that popped into oddsmaker Jimmy Vaccaro’s head in early February 1990, though at the time it didn’t seem to matter. There was no way Buster Douglas was going to go to Japan and beat the baddest man on the planet, so 27–1 seemed like a reasonable line for what everyone figured would be a short fight with Mike Tyson.

Except it wasn’t. The next day a customer came in and bet $54,000 to win $2,000 on the expected Tyson beatdown. Others soon followed, handing over fistfuls of $100 bills across the counter at the Mirage hotel sportsbook.

If anything seemed like a sure thing in 1990 it was that Tyson would knock out Douglas to retain his heavyweight titles.

“To this day I’ve never seen so many people who would lay such a big price on anything,” Vaccaro said. “The number went to 37–1 and then finally to where it ended up.”

That would be 42–1, a number that still lives in sports betting lore. The line at the Mirage became so iconic that an ESPN documentary on the fight was named after it, and bookies still talk about it anytime the most storied odds come up in conversation.

The line seemed fair enough at the time, mostly because nobody thought Tyson could possibly lose. Not even the guys behind the counter at the Mirage sportsbook.

“I was in my office and the word came in that Douglas won,” Vaccaro said. “I told the kids who put the final scores not to put it in the system because I thought it had to be wrong and I didn’t want to end up paying both sides. A half hour later we got the official news and I just said, ‘Wow’ and went home.”

It was 30 years ago Tuesday that Douglas, a journeyman heavyweight who never seemed to fight to his potential, came off the canvas to stop Tyson in the 10th round at the Tokyo Dome. It was the first loss for Tyson, the savage punching heavyweight who was so feared that other fighters often seemed petrified to even get in the ring with him.

What bettors putting their money on Tyson at the Mirage didn’t know was that the heavyweight champion was a mess. He had a new trainer, was embroiled in personal problems and barely trained for what was expected to be yet another easy night’s work.

Douglas, on the other hand, was on a mission to win for his late mother. He did what no other fighter dared, bullying the bully into submission to begin what would be a short reign of his own as the heavyweight champion — one that, ironically enough, would soon be cut short just a short stroll from the sportsbook Vaccaro ran at the Mirage.

A lot of $20 bettors won money on the fight at the Mirage, Steve Wynn’s glittering new resort that had opened just three months earlier. But the big bettors put so much money on Tyson that the hotel would win about $300,000 on the bout.

“They thought it was an automatic win, just give Jimmy your money for an hour or two and he’ll give it back — and then some,” Vaccaro recalled. “I’ll never forget a big Los Angeles customer who laid some ridiculous figure just to win $4,000 at 42–1 on the favorite.”

The resulting publicity was worth many millions more for a hotel that changed the look on the Las Vegas Strip.

The stunning loss became huge news, and the odds became a big part of the story. Sports writers who didn’t travel to Japan because they expected a big win were now writing about a little–known heavyweight who had beaten 42–1 odds to score one of the biggest upsets in sports history.

For Vaccaro in those pre–cellphone days, it meant his beeper was filled the next day with endless call–back numbers from media wanting to know if it was the biggest upset ever.

If not, it was pretty close, ranking up there with the Jets’win as 18–point underdogs in Super Bowl 3.

It wasn’t the last Vaccaro would see of Douglas, whom Wynn quickly signed to defend his title at the Mirage. Five months after he beat Tyson, Douglas went down on one punch by Evander Holyfield in the third round and stayed down, much to the displeasure of Wynn and the fans who had expected to see a competitive heavyweight title fight.

Today, Douglas is long since retired and teaches boxing to kids. Tyson is still Tyson, earning his keep these days as a founder of a marijuana company and as host of a podcast where much weed is smoked.

Vaccaro, meanwhile, is back in Las Vegas after a brief return home to make odds in Pennsylvania. At the age of 74 he’s a legend in Las Vegas bookkeeping circles, presiding over business daily at the Southpoint hotel’s sportsbook.

Sports betting is spreading across the nation, thanks to a Supreme Court ruling that allowed states other than Nevada to make it legal. An industry that operated on the fringes of normal society has now gone so mainstream that even the biggest sports leagues are now partners with the very bookmakers they once despised.

A lot has changed since Vaccaro put up a line that helped change sports betting forever.

“We were still the bad guys,” Vaccaro said. “Whatever the bookmakers did was no good. We had this black cloud hanging over our heads. But that opened up a whole new box at that point. The publicity was through the roof.”