A Mystery Series Bets on the Changing World of Sports Wagers 

While growing up in West Chicago, Tom Farrell was immersed in sports: He was a member of his high school golf, basketball, and football teams, and he worked as a golf starter at the local St. Andrews Country Club throughout the late ’60s and early ’70s. And when he wasn’t playing himself or helping to manage the flow of politicos and corporate outings on the golf course, he was reading about the intricacies of sports handicapping. The way that experts play the odds would become a lifelong fascination that eventually inspired his series of murder mystery thrillers, including 2021’s Wager Tough. 

“It’s not about betting on a horse because you like the horse’s name,” Farrell says, explaining the practice of handicapping. For him, it is the art of examining a multitude of factors and looking at different information to make a prediction that goes beyond an educated guess.

Farrell kept up with sports and handicapping even through a diverse career. He worked as a chemist after graduating from Knox College, then went on to practice law in Denver, Colorado, all while pursuing writing on the side. And whether at the golf course or at the racetrack, being a handicapper and sports fan inevitably puts one in contact with the (previously illegal) world of sports betting. 

“When you grow up in Chicago, the Outfit, as the mob was known in Chicago, was a part of everyday life,” Farrell says. “Corruption was the cost of doing business.” Since sports betting had long been a major cash cow for the Mafia, writing about handicapping and betting seemed like the perfect entry point for Farrell to explore his interest in writing a mystery novel. In Wager Tough, he puts readers in the shoes of handicapper and gambler Eddie O’Connell, who is in deep debt with the Chicago Burrascano crime family, blending Farrell’s love for sports and writers like Dennis Lehane, Michael Connelly, and George Pelecanos.

Wager Tough’s clever twist is that the mob uses its leverage against Eddie not to get the money he owes them but to employ him to solve a murder. Eddie isn’t an investigator, per se, but he and his retired-homicide-detective uncle often take on investigations for the mob (with the caveat that anyone they catch be handed over to the police instead of facing Mafia-style justice). In Wager Tough, however, the bosses force Eddie out on his own, sending him to Denver, and the case is personal since he and his uncle knew the victim, Zany, a mob-backed bookie and former jockey. 

Kirkus Reivews named Wager Tough one of the Best Indie Books of 2021 and cited Farrell’s “pitch-perfect ear for the intricacies of the no man’s land Eddie inhabits.” With sharp, first-person narration, Farrell gets inside Eddie’s head as he finds himself out of his element in Denver, trying to track down suspects by collecting from the gamblers who owed Zany:

They acted like Zany had done them a favor by taking their wagers. But I couldn’t walk into the club, introduce myself, and lay down new rules. I had to stay in control. Collecting gambling debts, a debt based on an illegal activity, was a bluff. You didn’t want to push the debtor toward the authorities. It was a different story in Chicago where collectors operated under the mob’s protective umbrella of rumor and innuendo. Run to the cops and they’d laugh at you and club you with a nightstick to cure you of stupidity. But here in Denver?

The idea to put Chicago gangsters against a backdrop of Rocky Mountain vistas came, in part, from Farrell’s local poker group in Denver, where he had a friend who was a bookie. The two would trade books, especially on sports betting, and talk about the local scene. “This idea that there’s no mob in Denver and that they have no corruption here in this town is certainly not true,” says Farrell.

Farrell himself first moved to Denver in 1979 after attending law school at DePaul University in Chicago. He practiced mostly commercial law until retiring in 2012 and devoting himself to working on writing. While penning Wager Tough, which is set in 2014, he did extensive research to further his knowledge by interviewing detectives and sports-book managers in Las Vegas and attending sports betting conferences. 

By 2017, Farrell was already at work on a second book, Wager Easy, when the Supreme Court heard oral arguments on legalizing sports betting. By the time the decision came down in favor of sports betting in 2018, Farrell was already deep into a world suddenly changing by the minute. “The big question is not only how are the states going to structure sports betting laws,” Farrell explains, “but [also] what’s going to happen to the bookies? How are they going to survive?”

The legalization of sports betting did not deter Farrell from wanting to continue the adventures of Eddie O’Connell. In fact, his early ideas for Wager Easy proved quite prescient, so he worked the Supreme Court decision into the story and published that book first, deciding against a strictly chronological series. Currently, Farrell is finalizing a third Eddie O’Connell mystery that will take place in Las Vegas, and Farrell is eager to keep exploring the shifting landscape—especially as questions of regulation between states make it even easier for the former lawyer to work his interest in the law into his thrillers. 

No matter where the series or sports betting goes from here, Farrell finds that Wager Tough and Wager Easy make nice bookends on the way sports betting changed in America over the last decade. They also show that there are problems and plenty of dramatic possibilities with sports betting, be it illegal or legal. “A lot of people think legalization is going to add to the integrity of sports betting,” Farrell says. “I’m just not convinced that’s true.”

Rhett Morgan is a writer and translator based in Paris.