LAS VEGAS — When you spend nearly five decades working in Las Vegas, you have stories to tell. Jimmy Vaccaro would run out of time before he'd run out of stories.

Vaccaro is one of the legends in Las Vegas sports betting history, one of the first to manage a sports book and a fixture in the city who has been setting odds since the 1970s. When the Sports Gambling Hall of Fame was formed in 2023, Vaccaro was part of the 10-person inaugural class. He's one of the legendary oddsmakers in Las Vegas history.

"He’s one of the most famous now," said South Point sports book director Chris Andrews, a decades-long friend of Vaccaro. "How do you rate them? It's like, who’s the best guitar player in the world? Everyone has their opinion on it. He’s certainly in the conversation."

Vaccaro isn't unfamiliar with fame and attention. His brother, Sonny, was played by Matt Damon in the movie "Air," the story of Sonny Vaccaro convincing Nike to sign Michael Jordan.

Vaccaro has stories to tell, and he'll often interrupt himself to start one.

"I was on 'The Simpsons,'" Vaccaro said. "You didn’t know that?"

"The Simpsons"? Like Homer, Marge and Bart, those Simpsons?

"Want to punch it up? You can punch it up," Vaccaro said, turning to a computer near him, almost egging you to search for him on the internet.

Vaccaro said Alan Feldman, then the marketing director for The Mirage casino in Las Vegas, came to him with the opportunity to be on the popular show in 1995.

"I didn’t know what 'The Simpsons' were," Vaccaro said. "Now, my two kids did because that was in their zone. I said, 'Yeah, whatever.'"

He explained how he had to find a different color shirt (other than white) because of how it would look on camera, how he gave the fake betting odds on who shot Mr. Burns and even how royalties work after you've been on a TV show. He laughed at how classmates heard that his kids' dad had been on "The Simpsons," and that became a thing at school.

"So, I was on 'The Simpsons,'" he said.

This is what a visit with Vaccaro is like. This one took place in mid December, about six weeks before Vaccaro's beloved Las Vegas played host to the Super Bowl this week. Most days, he is hanging around the South Point sports book, about a 15-minute drive from the south end of The Strip, advising the oddsmaking team there, wearing his comfortable sweatshirt and always willing to share a story.

When you're one of the most famous figures in Las Vegas gaming history, you have plenty of stories to tell.

The glory days of Vegas' big boxing matches 

Super Bowl LVIII will be played in Las Vegas. It's not the first time the city has hosted a big sporting event.

The big boxing matches are what Vaccaro remembers most fondly from his career. Muhammad Ali's last big fight, against Larry Holmes at Caesars Palace in 1980, stands out. And here comes another Vaccaro story, this one about the time he had a customer from Detroit, with a woman on each arm, come in wanting to bet on Tommy Hearns in a big fight. Vaccaro asked him how much he wanted on Hearns.

"He says, ‘I don’t know. What do you think, girls?’ They’re giggling," Vaccaro said. "He says, ‘How about $40,000?’

"You can only imagine how long it would take to count out $20 bills for $40,000. I’ll never forget it."

Back in the glory days of big boxing matches in Las Vegas, there weren't nearly as many sports books in the city as there are now. There were only a handful, which is part of what makes Vaccaro such a big figure in sports betting history. He ran multiple sports books through the years, starting at Barbary Coast and eventually moving to The Mirage, MGM Grand and Golden Nugget. When the fights came to town, people wanted to bet, and Vaccaro's sports book was one of their only options.

"The boxing was incredible," Vaccaro said. "We went through about 15 years where every four or five months was a monster fight. Forget this UFC garbage."

Sitting nearby in a side office as he listens to Vaccaro tell his old stories, Andrews chimed in: “We had like three or four extra Super Bowls a year with these fights.”

"The fights were incredible," Vaccaro continued. "And I loved them. Never stopped loving 'em."

A memorable fight led to Vaccaro's most famous moment. Want to hear a story?

42-to-1

Vaccaro loved putting up odds on boxing matches, even a 1990 mismatch between the seemingly invincible Mike Tyson and a no-name such as Buster Douglas.

"I was putting up odds on all those fights because I enjoyed it," Vaccaro said. "So now here it is, it’s like, ‘Wow.’ Nobody would book the fight because the odds were too high. So I said, ‘I’ve got to do this because I’ll be the only one.’"

In a previous Tyson fight, Vaccaro opened Michael Spinks as an 8-to-1 underdog, and so many people bet Tyson that the odds moved to 15-to-1. Tyson won in 91 seconds.

For the Douglas fight? Vaccaro's sports book at The Mirage was the only one to set a line. He set it at 27-to-1.

"That was the opening line," Vaccaro said. "A guy I know pretty well, he was a bettor every day, he laid the 27. He laid $54,000 to win $2,000. Because he thought it was just a pickup. You know, 10 minutes later, I’m going to get my money.

"I changed it to 31-to-1. Another one of my big boxing bettors from L.A. came to town. 'Jimmy, I heard you had this fight.’ It’s 31-to-1. He bet $93,000 to win $3,000 at 31-to-1 or whatever it was. Then people started to hear about it. It just didn’t stop. I got to 42-to-1."

In 2018, ESPN made a documentary on the Tyson-Douglas fight as part of its "30 for 30" series. The title was "42 to 1."

"You’ll like this," Vaccaro said. "The number is 42-to-1. This is the day of the fight. Guy came in, he was a customer at The Mirage. He laid $420,000 at 42-to-1 to win $10,000. I’ll never forget.

"Somebody was standing there, I think it was a newspaper guy. I said, ‘He thought he was going to pick up $10,000 in about five minutes, when they rang the bell.’"

Well, Tyson lost in one of the biggest upsets in sports history. Vaccaro said he didn't believe the ticker when it said Tyson lost the fight, which was in Tokyo. He didn't pay out the bets on Douglas until news stations such as ESPN started reporting it.

Then Vaccaro went home, and at about 5 a.m., he started getting calls from The Mirage saying they were receiving multiple interview requests. The Mirage, thanks to Vaccaro, was the only sports book that had a line on Tyson vs. Douglas. He came back in to do all the interviews.

"So you can only imagine the vibration through the whole freaking world," Vaccaro said. "Now remember, if Tyson would have won, there would have been nobody calling us."

Soon, 42-to-1 became part of the lore of one of the most famous fights in boxing history.

"I'll live with that one for a long time," Vaccaro said. "It’s a good feeling. Nobody else did it."

How Vaccaro built his name in Vegas

Got time for another story? Sure you do.

"I was the first one to make overs and unders on season win totals," Vaccaro said as soon as he finished the Tyson-Douglas story.

In 1989, he had customers in from Texas who wanted to know how many wins Vaccaro thought the Dallas Cowboys would get with new head coach Jimmy Johnson. He thought about it a while, and he set a line: 5.5 wins. One of the bettors wanted the over. His wife had a purse on her shoulder.

"She turned her purse over, and all these wrapped $10,000 of bills are in there," Vaccaro said. "He bet $38,500 to win $35,000 on the over."

The Cowboys went 1-15, but that started the trend of sports books posting season win totals for teams. Today, it's one of the most popular markets in sports betting.

The stories don't stop. One time, when Vaccaro was running the sports book at The Mirage, the book had a terrible day and lost $1.4 million. Vaccaro got a call from casino/resort owner Steve Wynn.

"I walk in there, and he says, ‘What the hell did you do?’ I said, 'We have good days, too, Steve,'" Vaccaro said, perhaps unaware that not many people have to answer to their boss after losing more than a million dollars. "He said, ‘Go back, and do what you’re doing, and keep doing it.’"

The stories go all the way back to his origins in Las Vegas. He first drove to Vegas from Trafford, Pennsylvania, when he was 18. After he turned 21, he'd go to Vegas "every time I had a little bit of money" and go home when he was broke. After a few years, a friend remarked that he should just stay in Vegas. And in 1975, he did. He went to see casino owner Michael Gaughan and asked for a job. Gaughan said he could become a blackjack dealer; it just took $250 to go to a dealer school that Gaughan owned.

"I had, like, $40, I think," Vaccaro said.

Gaughan let Vaccaro pay him back when he had the money.

You won't be surprised to hear that Vaccaro also has a story about how he got into the sports betting business in which he became a legend. One day, Gaughan called him up to his office.

"If I live to be 10 million years old, this is what he said, because it changed my life," Vaccaro said. "He said, ‘Do you know how to run a sports book?’ I said, ‘No!’ I was just a kid like him, betting, but never running a sports book.

"He said, ‘Good, neither do I.’"

Vaccaro was put in charge of a little sports book at the Royal Inn, which was imploded in 2015. There were only a few other sports books in Las Vegas at the time. That grew until practically every casino had one. Then a Supreme Court decision in 2018 allowed states to legalize sports gambling. Legal sports betting exploded afterward. Sports betting going mainstream is likely part of the reason the Super Bowl is in Las Vegas. That explosion traces back, at least in part, to Vaccaro setting lines for Ali-Holmes, taking $40,000 bets on Tommy Hearns, making the first win total odds for the 1989 Cowboys and giving sports betting invaluable exposure with the Tyson-Douglas line.

There are many more stories from his lifetime of oddsmaking, such as the time legendary poker player Stu Ungar was being treated in his office after having a heart attack but still wanted to bet ("'Where's Jimmy? I want the Cowboys for $30,000!'" Vaccaro said. "Everybody was staring. I said, 'You're going to f***ing die!' He said, 'Jimmy, give me the bet!'") or the time his was the first sports book to take a big bet from from Mattress Mack, the owner of the Gallery Furniture chain in Houston who has become famous in the betting world for massive wagers, which are sometimes eight figures and usually on Houston teams ("He's a gentleman," Vaccaro said. "We have nothing but good things to say about each other.").

Along the way, Vaccaro played his part in bringing sports betting to the mainstream.

"I was probably the only one who said, ‘We ain’t seen nothing yet,’ way back when it started," he said. "We’re not geniuses. We just left the door open for a little bit."