Horseplayers are never happy.

Their three favorite words are “woulda,” “coulda,” and “shoulda,” which is the title of a book by the late Sun-Times handicapper Dave Feldman, who used to roam around the paddocks of the Chicago tracks in a fur coat.

“I woulda hit the Daily Double if the bus had gotten here in time for the first race.”

“I coulda had the trifecta if I’d’a used the 8 horse in the third spot.”

Even when they win, they’re not happy.

“I bet a fin on the 2 and he came in. I shoulda bet 20!”

Since Arlington Park closed in 2021, there is only one racetrack left in the Chicago area — Hawthorne Race Course — and it only runs twice a week, on Thursdays and Sundays. That means horseplayers have fewer places to bitch, and fewer opportunities to do so — but it also means they have more to bitch about.

Hawthorne is, supposedly, in the middle of a $400 million conversion to a “racino” — a combination horse track and casino. They’ve torn up the grandstand to make room for slot machines and craps tables, but have not been able to obtain financing for the project. As a result, the horseplayers have been crowded into a corner of the clubhouse, a furlong north of the finish line. From there, we could see the sights of Stickney — the world’s largest sewage treatment plant, the oil refinery, the jets landing at Midway — but not the horses “spinning out of the turn,” as Hawthorne announcer Phil Georgeff used to shout.

“They certainly don’t make it easy to see the horses,” a gambler complained as he waited for the horses to charge down the stretch in the first race on a recent Sunday. I’ll call him “Carp,” because every good horseplayer deserves a nickname. “The jockeys are thinking, ‘Is anybody here?’ They only run twice a week. Why do the jockeys even ride here?”

Twenty years ago, I wrote a book called Horseplayers: Life at the Track. It was about spending a year trying to beat the races, and all the oddball bettors I met along the way: Bob the Brain, Bias Bill, David the Owl, the Professor, the Stat Man, Lucky. None of those guys were around on Sunday. Back then, Hawthorne raced five days a week, nine races a day, often with 12 horses in a race — which meant better odds, because the action was spread out among more entrants. I once hit a $1,200 exacta on a 12-horse field. Hawthorne was a ‘B’ level track — not Saratoga or Santa Anita, but the winner of the $750,000 Illinois Derby was guaranteed a spot in the Kentucky Derby. 

The Illinois Derby hasn’t been run since 2017. Wagering on horse racing in this state has dropped from $1.3 billion in 1992 to $600 million today, reducing Hawthorne to a minor regional racetrack — “a tiny little corner, both literally and figuratively,” according to a chart caller.

“I don’t know why anybody comes here,” Carp carped. “There’s no money.”

In the 4th race, I bet $2 on a horse named Follow the Signs, because I liked his trainer. (The attitudes of the mutuel clerks haven’t changed. I paid for my bet with a fin — a $5 bill. The clerk threw three singles across his ticket machine, as if to say, “Get your ass out of here with that weak action, you nit.”) I got 2-1 odds — a $6 payoff. I shoulda bet a fin. After I cashed my ticket, I ran into my old racetrack buddy Marc. I once dubbed Marc the Hipster Horseplayer, because he wears chunky glasses and cardigans, and lives in a basement in Old Irving Park. Like everyone else in the joint, Marc bitched about the quality of racing at Hawthorne.

“I’ve been betting on horses from Turfway,” a racetrack in Kentucky, he said. “These horses from Turfway can beat these crappy Hawthorne horses. It’s sad. Those claiming races, we call ’em pigs. It used to be mid-level racing. My brother and I, we get into knock-down, drag-out fights. He only bets Hawthorne. He’ll bet a hundred dollars. I tell him, ‘You can’t take these races seriously!’ Jim Benes” — a.k.a. Blonde Jimmy, an intense Hawthorne horseplayer who once won $750,000 in the National Handicapping Championship — “he told us, ‘You can’t beat these small fields.’”

That Sunday, though, Marc beat the races.

“I hate this race,” I told him before the 7th, an allowance for horses that have never won a high-class race. “None of these pigs look like they want to win. I really like Be My Bestie in the 8th. I’m gonna bet all the longshots here with her in the Daily Double” — a bet requiring a gambler to pick the winner of two consecutive races.

“I kinda like Raceday Attire here,” Marc said. “He’s 30-1 right now.”

Marc bet $3 to win on Raceday Attire. I bet the Daily Double. 

“Dollar double: 1, 4, 6, 7, 8, 9, with 3,” I instructed the teller. It cost me a whole six bucks, but he didn’t seem any more impressed.

Raceday Attire won and paid $40.20 for a $2 bet. Marc collected $60.40.

“You’re gonna get a great price on your Daily Double,” Marc reassured me. “It’ll probably pay over a hundred!”

“If it comes in. If I’d just bet straight like you, I’d be ahead now.”

I thought Be My Bestie was going to win. I really did. She took the lead early and ran along the rail, the inside part of the track. She was still winning with an eighth of a mile to go, then a sixteenth. But as the Daily Racing Form would put it, the 8 horse, Wildwood Triple, “made a three wide bid and had a long drive the final furlong and won the head bob to prevail.” The finish was so close I had to watch the replay on a TV screen to confirm the result. Wildwood Triple’s nose dipped down at the wire, a nostril ahead of Be My Bestie. 

I lost $9 on the day. If I’d’a bet like Marc, I’d’a won $30.

Woulda, coulda, shoulda. Horse racing in Chicago may not be as classy as it used to be, but a gambler can still go home full of regrets.