Caesars sportsbook executive Adam Pullen has taken sizeable bets in his two-plus decades establishing the betting lines for the Super Bowl.

Just not a six-figure wager on which side a coin will land.

That changed when a gambler visiting the famed Las Vegas casino plopped down $100,000 on the outcome of the opening coin toss Sunday night for Super Bowl LVIII between the San Francisco 49ers and Kansas City Chiefs.

The bet was on tails.

“He’s either going to be in the hole or up big before the game even starts,” said Pullen, the assistant director of trading at Caesars in Las Vegas.

The coin toss is one of the more popular prop bets — a wager that isn’t tied to the outcome of the game — for the Super Bowl. It’s among the hundreds of ways bettors can place a wager on an individual performance or sequence that is unrelated to the final score.

“Each play, once the game has started, there are bets being decided,” Pullen said. “It just shows how Super Bowl betting and betting in general has transformed the country. This used to be a closet Vegas thing. Now it’s everywhere.”

Prop betting’s origins can be traced to January 1986 when the Chicago Bears’ 335-pound defensive lineman William “The Refrigerator” Perry scored a touchdown during a 46-10 rout of the New England Patriots. Trafford native and Sports Gambling Hall of Fame charter member Jimmy Vaccaro was one of the few oddsmakers who had established odds on whether the big man would find the end zone.

When word of the bet spread, Vaccaro began receiving calls from sports writers across the country curious about the wager.

“It was pure insanity,” Vaccaro said. “From that point, if there was anything unique, we as bookmakers would find a way to make a wager out of it.”

The popularity of prop bets increased exponentially in 2018 when a Supreme Court decision cleared the way for states to authorize legalized sports betting. That made it legal for a gambler to place a bet on whether the opening kickoff will be returned or a touchback or whether Chiefs star quarterback Patrick Mahomes will have 300 yards passing.

“It’s also a correlation of the popularity of playing fantasy sports,” said Stephen Andress, editor of the sports gambling site TheLines.com. “Because of fantasy football, bettors are aware of which player is the best, who has the most yards, who is struggling. Now they could make a bet on any given game based on their fantasy sports opinions.”

Andress estimates that 40% of all legal wagering on the Super Bowl will be in the form of a prop bet. Vaccaro puts that percentage higher.

“I think it’s half, which is an unbelievable number,” he said. “Half are betting on the outcome of the game, and half are using their money on props. That way, you’re entertained the entire game. From the flip of the coin until who scores last, you’re always in the action.”

BetMGM sportsbook has about 1,000 prop bet offerings, with several tied to Chiefs tight end Travis Kelce. Not just because Kelce’s track record as a Hall of Fame talent and a big-game player but also for his relationship with pop singer Taylor Swift.

Sportsbooks cannot legally accept a prop bet on the singer — such as whether Kelce will propose and each will get a ring after the game — much to the dismay of Swifties worldwide. Wagering must be confined to what takes place on the field. Kelce represents the next best thing.

One DraftKings wager, with ties to the Swift song “Wildest Dreams,” centers on whether Kelce will score the first and last touchdown of the game. A takeoff on the song “You Belong With Me” is the “You Belong with Rashee” wager. It is based on whether Chiefs receiver Rashee Rice will score a touchdown in the first half.

A loophole on Swift-related prop bets, however, can be found outside the U.S. Ontario is one territory where bettors can find such action.

“There is more lenience, more novelty and fun props,” said John Ewing, BetMGM PR manager. “For instance, will the MVP mention Taylor Swift at all? Since Travis Kelce is the most bet player to win the MVP, bettors are thinking that if he wins the MVP, he’ll give his girlfriend a shoutout.”

The number of wagers on the Super Bowl can be staggering, something Vaccaro never predicted when he left Western Pennsylvania for Las Vegas in the 1970s. Vaccaro, now 78, was in his infancy as a bookmaker when the Steelers played the Dallas Cowboys in Super Bowl XIII in January 1979.

The point spread was the wager back then. One promotion offered bettors the chance to give 3.5 points with the Steelers and take 4.5 points and the Cowboys. The Steelers’ 35-31 victory ensured almost everybody who bet on the game was a winner.

That game became known as “Black Sunday” in Las Vegas gambling circles.

“We got our (butt) kicked,” Vaccaro said.

Vaccaro had the task of delivering the message to his boss.

“I said, ‘Do you want the good news or the bad news?’” Vaccaro recalled. “The bad news is we lost $185,000, which was a pretty significant number in those days.”

Vaccaro’s boss incredulously asked about the good news.

“We only lost $185,000,” he said, recalling the exchange. “A lot of other places got hit harder than we did.”

This year, that type of six-figure wager has been placed on the outcome of the coin toss, as Pullen can attest.

“It boggles my mind,” he said, “that someone would bet that much money on that.”

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