By David Purdum

The greeting on the Chicago bookie’s answering machine often began with insults and ultimatums.

“42, up yours,” he would bark, calling out account numbers of clients in poor standing. “63, I better see you at the bar to settle up or I’ll come find you. Now, here’s the lines.”

Bettors jotted down the point spreads on the day’s games then left a message after the beep: “This is 63, give me the Bulls for a hundred. Yeah, yeah, I’ll see you at the bar.”

This was neighborhood bookmaking in Chicago in the 1990s. It was raw and rudimentary, but it was everywhere in a time when Michael Jordan and the Bulls were the biggest show in sports.

Twenty-two years ago—on June 14, 1998—Chicago bars erupted as Jordan crossed over Utah’s Byron Russell and hit a game-winning jumper in Game 6 of the NBA Finals. Not only had the Bulls just won their sixth title in eight years, but they also covered the spread as 2-point underdogs. Which outcome resonated more in a city that loves to bet depends on whom you ask. As one veteran Chicago bettor who goes by Geno put it, “When the Bulls were playing, well, it’s not whether they were going to win but just by how many.”

Illinois didn’t legalize sportsbooks until 2019, long after Jordan had hung up his high tops, but sports betting has always been part of the soul of Chicago, with bookmaking a commonplace, albeit underground, profession that dates back over a century in the Windy City.

Bartenders in nightlife hot spots like Lincoln Park normally had connections to a bookmaker, as did the staffs at local country clubs. The heaviest sports betting in town, though, took place at 141 W. Jackson Blvd., on the floors of the Chicago Board of Trade (CBOT).

“It was the first time I was exposed to a true sports betting culture,” said Jeff Ma, who, after spearheading the famed MIT blackjack card-counting team, came to Chicago in the mid-1990s to work as an options trader. “The culture of betting was just pervasive.”

‘Breeding ground for bookmakers’

The grey Art Deco skyscraper on the corner of LaSalle Street and Jackson Boulevard is home to the CBOT. It’s the Wall Street of the Windy City, to a degree. A statue of the Roman goddess of agriculture sits on the roof, and eight bovine heads representing the livestock once bought and sold inside adorn the façade above the original trading floor. It has been a breeding ground for Chicago bookmakers for decades.

The gambling culture at the CBOT spawned colorful characters and wild tales. The bookie who ran his operation on his answering machine worked at the CBOT in the 1990s, alongside many other clerks and traders who battled in the pits during the day and moonlighted as bookmakers on nights and weekends.

“In the pits, there was some pretty big money flying around,” said a former trader and freelance bookmaker who preferred to speak anonymously. “Hundreds of thousands of dollars would be wagered on the Bears’ over/under [on wins in a season]. That was back in the day, though, when the floors were jam-packed.”

One bookmaker was working at the mercantile exchange in the early 1990s, when he scored an early model cell phone that was so clunky, it required a bag to lug it around anywhere. At the time, however, it was cutting-edge technology, and a significant advantage over bookmakers reliant on landlines. The mercantile bookie grew, and the wrong people began to take notice. To avoid detection from authorities and organized crime, the bookmaker and his partner decided to use the bag phone to move their operation offshore.

On weekend mornings, they would drive their boat down the Chicago River, past the bars and clubs that often playfully shoot water cannons at approaching vessels, and out onto Lake Michigan to take the bets over the bag phone. It was the perfect setup, they thought.

On one busy Saturday morning, after logging hundreds of college football bets on pieces of rice paper from the boat, they headed to one of the bars on the river. A buddy at the bar spotted them pulling up and blasted them with the water cannon, drenching the boat and the rice paper with the bets. Writing on rice paper disappears when it gets wet. The record of the day’s bets was gone.

After discussion, legend has it that the bookies chose to pretend as if nothing had happened. When bettors called to confirm their balance the next day, the bookies didn’t question the figures, even though they had no clue how they actually made out on Saturday’s games. No one ever knew.

“Infamously, the bank in the Board of Trade building had more cash in hand than any other bank in Chicago, because people are going in there and getting gobs of cash to pay their guy [bookmaker],” Brian Timpone, a Chicago native, said.

Established in 1848, the CBOT was the first grain futures exchange in the U.S. At its peak in the 1980s and 90s, it claimed to be the largest futures exchange in the world. Everything from pig bellies to point spreads were traded on the CBOT floors.

“On the floor, you basically had a secondary exchange for buying and selling college basketball teams,” Ma, the blackjack whiz and former trader, said. “To the point, you’d literally walk around with a trading card and talk about all the trades that you made that were college basketball teams. You were just walking around trading them with people.

“There was another time,” Ma added, “when there was a challenge to eat 20 cheeseburgers at McDonald’s. There were thousands of dollars changing hands on whether this guy was able to eat 20 cheeseburgers.”

From Capone to Lefty: Chicago’s bookmaking lineage

In the 1900s, bookmakers Mont Tennes and “Big” Jim O’Leary ran sports betting in Chicago. Tennes, a North-Sider, introduced parlay betting on baseball in 1908, and, according to news reports, took a bath, when popular favorites like the Chicago Cubs, New York Giants and Detroit Tigers piled up win after win. O’Leary came from the South Side and ran his operation near the Stockyards in the shadows of Comiskey Park, before suffering a loss from which he could not recover.

“O’Leary was not in on the fix of the [1919] World Series,” Kevin Braig, an Ohio judge and sports betting historian, said. “He took a beating and had to exit the business.”

Mobster Al Capone arrived in the Roaring Twenties and played both sides of the business, taking a cut from many of the city’s bookmakers, while also betting heavily on the ponies, rather unsuccessfully, some say.

“Capone was believed to be more of a buyer than a seller of wagers and reportedly lost hundreds of thousands of dollars backing the ponies,” Braig noted.

The Chicago Outfit, as the city’s organized crime network was known, maintained a piece of the vibrant underground sports betting market for decades. In the 1970s, they expanded to Las Vegas through bookmaker Frank “Lefty” Rosenthal, a native of the Westside of Chicago who was portrayed by Robert De Niro in the movie “Casino.” Rosenthal would run the sportsbook at the ionic Stardust resort in Las Vegas and later emerged as a local celebrity, hosting his own variety show with guests like Frank Sinatra and O.J. Simpson. In 1987, after a flamboyant career, Rosenthal was put in the Nevada Black Book, essentially banning him from the gaming industry.

Meanwhile, bookmaking in Chicago continued. Michael “Jaws” Giorango, a longtime notorious figure in the city, was convicted on federal bookmaking charges twice in 1989 and 1991. In 2004, Giorango took another rap for his role in a nationwide prostitution ring known as The Circuit.

And just this February, 10 men — including Casey Urlacher, a small-town mayor in Illinois and brother of Chicago Bears’ great Brian Urlacher — were indicted on gambling charges related to an offshore sports betting operation allegedly run by a local businessman who goes by “Uncle Mick.”

Indeed, Chicago has a rich bookmaking history, and the 1990s were no exception. Sports betting just looked a little different back then than it does now.

Windy City wagering

Word of mouth was the easiest way to find a bookmaker in the 1990s in Chicago. Getting your buddy to vouch for you with his bookie was the most common way to gain access to the underground sports betting market.

There was an abundance of small-time bookmakers. Some were up-and-comers from the neighborhood. Others were young hotshots who took bets in college and thought they could handle booking in the big city. The problem for the low-level bookmakers was scale. If they grew big enough, they might receive a call from the local Outfit wise guys, offering a business proposition they were expected to accept.

Life was a little less un-nerving for most Chicago bettors, who received an account number, a phone number to call in their bets and a “settle-up amount.” If your account balance was up or down $500, for example, you needed to meet the man. Losers had to pay on Mondays; winners collected on Wednesdays. Settling-up took place in person and mostly in cash.

Pre-internet, the point spreads in the newspapers, either the Chicago Tribune or the Chicago Sun-Times, were the standard in the city. It didn’t matter that the odds were set the previous night in order to make the printing deadline – the newspaper line was what bettors went by and what bookmakers normally offered.

“I do remember some books would have the newspaper line plus a point and a half, meaning if the Bulls were 11, you had to lay 12.5,” recalled a Chicago native and longtime sports bettor who asked to speak anonymously.

In 1995, the bookie preferred by the kitchen and wait staff at Lansing (Illinois) Country Club also put the day’s lines on a recorded message. A female voice — the same one every time – would give the rundown, with the game number, the favorite and how many points they were laying: “604, Bulls 14. 606, Knicks 5.” When finished, she’d say, “Press 2 to place your bets.”

“This guy was pretty big. He had like a crew, the girl and a couple clerks,” Eric Waz, a busboy at Lansing Country Club and novice bettor at the time, said. “I don’t know how big the operation was, but it definitely wasn’t just a one-man show.”

Waz is now a sports bettor in Las Vegas and founder and CEO of sports handicapping website BettorIQ. He began his gambling education coming up in the Chicago area, though, betting around $50 or $60 a game with multiple bookies.

“For a lot of those Bulls’ years, I was still a teenager and was still learning the craft [of betting],” Waz said. “I was still betting parlays, making all the mistakes, taking all the favorites and overs and betting the Bulls a lot.”

Betting the Bulls wasn’t necessarily a square strategy: from the 1990-91 season through 97-98, Chicago went 591-201 straight-up and covered the spread in 54.2% of games.

Jordan’s gambling affinity

Illinois’ new legal sports betting market, once fully mature, could generate more than $10 billion in bets, according to industry consulting firm Eilers & Krejcik Gaming. That’s double the amount wagered with Nevada sportsbooks in 2019.

The Chicago underground betting market in the 1990s certainly wasn’t anywhere near that size, but it was ubiquitous around town – right when an awareness of Jordan’s affinity for gambling was reaching the mainstream.

The tales of MJ’s gambling exploits are legendary. On a road trip in Portland, he reportedly bet teammates $100 that his luggage would come out first at the airport. As the story goes, he bribed a baggage handler to make sure his bags were first. There were allegations of massive losses on the golf course, too, allegations that Jordan has maintained were overblown. When he left the NBA to pursue a baseball career, conspiracy theorists suggested that his gambling was a factor, something both he and former commissioner, the late David Stern, emphatically denied.

Yet, even in a city that loves to gamble, Jordan, at least publicly, avoided getting entangled with the local bookmakers, and, instead, soared to superstardom, transforming Chicago from a Bears’ town to a Bulls’ town in the 1990s.

“I never bet on games,” Jordan said on ESPN’s “The Last Dance.” “I only bet on myself, and that was golf.”

While Jordan says he wasn’t betting on games, plenty were with bookmakers of all levels of sophistication and means.

Perhaps one last tale from the Chicago Board of Trade best demonstrates city’s passion for sports betting. It takes us back to Championship Sunday of the 1998 NFL playoffs. A part-time bookie and determined bettor, who worked the trading floors, was preparing to have a party for the games at his apartment. But, before the party started, he ran until trouble at a Caribou Coffee in the hours before kickoff and ended up at the police station in Wrigleyville. When he called his friends from jail, he didn’t ask them to come get him out, but instead told them to grab a pen and take down his bets before the games kicked off.