My first day at Arlington Park was one of the most momentous of my life.

It was July 1, 1996. My father’s wife was in town for a conference, and he needed to kill an afternoon. He suggested the track.

Even before we walked inside, I was awed by Arlington. From Northwest Highway, the grandstand resembled a splendid resort hotel. Its roof, a cowl painted the green of ancient copper, floated above the summer trees. Outside the gate, a garden spelled out A-R-L-I-N-G-T-O-N in red begonias.

Inside, the very worst thing that can happen to a novice gambler happened to me: I won a lot of money. First I bet a fin on Flash Light, and a two-dollar exacta: Flash Light and A Sunny Delight. As the horses charged past my seat, Flash Light took the lead and hurtled down the stretch like a running back headed for the end zone. A Sunny Delight was right behind him. I won $48, and felt confident enough to attempt a trifecta. A beginning horseplayer picking a cold trifecta is like a guy who’s never held a dart shooting three straight bullseyes, but my horses ran 1-2-3, for a $100 score.

Just like that, a sport I had paid attention to once a year—Kentucky Derby Day—became the central focus of my life. I started going to the track or the State Street OTB (which has since been declassed to a Chick-Fil-A) every weekend. Then I started going every day, fantasizing about earning my living as a handicapper. I watched the race replays on TV every night. I clipped the results charts from the Sun-Times. I turned down a job promotion because it would have interfered with my gambling time.

A horseplayer is a guy who’ll bet $200 on a race, but won’t spend $20 on a pair of pants. For awhile, in my late 20s and early 30s, I was that guy. Eventually, I made the track pay. I wrote my first cover story for the Chicago Reader about my tutelage by a broken-down horseplayer at Sportsman’s Park. My first book, Horseplayers: Life at the Track, was about a year spent playing the horses. Getting hooked on gambling turned out to be great for my career.

Last Saturday, I spent what may be my last day at Arlington Park. The track is scheduled to close forever at the end of this meet. My press pass was labeled “2021 Race Season: The Final Turn.” Arlington’s owner, Churchill Downs, Inc., thinks placing a casino there—the only financially viable model for a modern racetrack—would compete with Rivers Casino in Des Plaines, in which it owns a majority stake. On this trip to Arlington, I won $15, by picking Bizzee Channel to win the Arlington Stakes.

I thought more, though, about what I and every other horseplayer in Chicago will be losing. Before the last race, I stood in the paddock and photographed the horses as the hotwalkers led them around the ring. The mellowing sun was declining over the Clubhouse Gate. A cool evening wind slid through the trees. Arlington is as serene as any public space in Chicagoland. It’s like the Botanic Gardens, with the bonus that you can win money.

When I first became a racetrack junkie, Chicago horseplayers followed four seasons: Sportsman’s, Arlington, Hawthorne and winter. After this year, it looks as though Hawthorne will be the last track standing. (Sportsman’s closed in 2002, after its owners made the disastrous decision to transform it into a combination horse racing/auto racing facility.) Hawthorne, on Cicero Avenue in Stickney, was the least glamorous of the three tracks, with a dank underground paddock and a minor league baseball-style grandstand overlooking the world’s largest sewage treatment plant. 

My first visit to Hawthorne was also unforgettable: standing on the poured concrete floor, on a Thursday afternoon, was the governor of Illinois, the Honorable Jim Edgar. Perfectly groomed and suited, the governor was clutching a race program and chatting with a broken-down horseplayer in a flannel shirt and baggy jeans. I knew why he was there: to watch his father-in-law’s horse, Lady Doc. I also knew that every time Edgar was at the track, Lady Doc won. I’d seen them together at Arlington. Coincidence? The governor’s presence was, as we say in handicapping, an angle. I bet on Lady Doc. She won.

Chicago has always been a second-tier racing circuit, not quite on the same level as New York, Florida, Kentucky or California. In recent years, though, as horse racing has lost market share to other forms of gambling, Chicago’s prestige has declined steeply. (In an era of increasing concern for animal welfare, horse racing is also becoming an atavism.) The Illinois Derby, which was once a Kentucky Derby prep—War Emblem won both races in 2002—has not been run at Hawthorne since 2017. The Arlington Million used to attract Europe’s fastest turf thoroughbreds; His Highness the Aga Khan entered a horse in the race. This year, the Million has been discounted to $600,000, and renamed the Mister D. Stakes, after Dick Duchossois, Arlington’s former owner.

Hawthorne, though, is promising to revive horse racing in Chicago. The track is spending $400 million to turn the grandstand into a racetrack/casino, with slots, table games and sports betting to supplement the horse racing—a racino, in the industry lingo. It’s scheduled to open by the end of 2022. I’ve been to racinos in Des Moines and Cleveland, and horse racing was a floor show. I had to walk through acres of slot machines to find the holdout horseplayers, leaning over the rail and handicapping short fields of cheap claimers. Hawthorne will be different, promises spokesman Dakota Shultz. 

“It often becomes, the casino is the main thing,” Shultz said. “Anybody walking into our facility is going to know there’s racing. It’s our identity. It’s going to be front and center, even right down to the design.”

With money from casino gambling, Hawthorne can also resume running lucrative stakes races, including the Illinois Derby, which in its prime offered a $750,000 purse and was heralded by a baritone belting out “My Kind of Town.”

“Perhaps even more than that,” Shultz said. “It can become a million-dollar race.”

However, a veteran handicapper I know, Scott McMannis, is skeptical that Chicago racing will return to its former glory from Hawthorne alone. A casino in industrial Stickney isn’t going to attract suburban families looking to spend a wholesome day at the races.

“They’ll be able to do the rudimentary things—use casino money to subsidize the product,” he said. “But the location and the drawing radius aren’t great. How much money is around the casino? And when you go there, you see all those smokestacks and those semi-trailers waiting to be hooked up.”

Guys like me will still play the horses at Hawthorne. Me and my bachelor horse racing buddies: Bob the Brain, David the Owl, Blonde Jimmy, Bias Bill, The Stat Man. We always liked betting Hawthorne better than Arlington, anyway. Hawthorne shipped in cheap horses from leaky-roof tracks all over the Midwest. That allowed them to run 12-horse races, which offer better odds for gamblers. I once hit a $1,240 exacta at Hawthorne—my biggest score ever. We’ll still be watching the races, but without Arlington, and with most of Hawthorne’s customers playing the slots, horse racing will become an ever-more marginal sport in Chicago.