When I was a little boy in Rochester, my Uncle Vin would often relieve my young stressed-out mother and take me with him on the 25-mile drive to pick up Aunt Florrie, his wife, from her job at the Finger Lakes Racetrack. Before I could read, this guy was showing me how to handicap a horse race.

Vin whiled away a fair number of hours along the backside (where the horses are stabled) amid the stalls and the trainers and the grooms, because his uncle, my great-uncle George Barone, was a legendary horseman at the upstate track. Another member of my fantastic, quirky family (all families are quirky) remembers that old Vin once claimed a horse, which means he bought the animal, but whether the claim was voided, or Aunt Florrie nixed the purchase, remains unclear, and the transaction never went through. Not long after that, my cousin Tom came along, and then my cousin Janet, and Aunt Florrie was at home raising her children. No more Finger Lakes, and certainly, no more silly talk of claiming racehorses.

I bloomed in the season of Secretariat, the best horse I ever saw, and I followed the improbable string of Triple Crown winners through the 1970s. Around that time a subset of would-be high rollers I occasionally attended high school with were making forays to the Lakes, pushing exactas and trifectas through the windows. A couple of the fellas enjoyed a profitable afternoon or two, after which, of course, the onslaught was on. Those winnings were lost, along with a lot more money, and this knot of ne’er do wells re-marshalled their appetite for risk into dimmer and darker pursuits.

Here’s something I used to brag about, although it’s only half-true: I didn’t place bets anywhere except at the racetrack. Aqueduct isn’t terribly far from where I sit in Brooklyn, but a ride on the A train can eat up sixty minutes, and the competition for my available hours was great. I was always trying to write, but I was always trying to make money, too, activities that are often mutually exclusive. Regarding the latter, I’ve long been stationed behind the bars of various watering holes, where, too frequently, I’m still standing: What’ll it be?

Several years ago, into my world wheeled a bon vivant, a writer and editor I met while working one of those bars. He was manning the weekend features desk at a major newspaper and encouraged me to write whatever I felt like writing. I contributed a couple of racing-themed articles to said features section, and there followed a spread about betting on horses that ran in a glossy magazine. The piece was illustrated by color photos of a handsomer version of myself, younger but bemused. Naturally, I cashed the checks, however all this exposure got me were phone calls from friends and acquaintances seeking my advice on the big race days.

***

I intended to be a not-terrible husband to my wife, and a father who remained present in the life of our daughter. (Her mother and I are still married. The two of them form my greatest asset). I didn’t have time for the track, I rarely cast my shadow at the now long gone OTB outlet on Delancey Street, and I’m the last guy to adopt any kind of technology—no betting apps clogged up the home screen of my phone. Not unlike a jockey with a hold on a headstrong colt, I kept my passion for horse racing under tight wraps.

Then, toward the end of Pandemic Summer 2020, with nothing to do and nowhere to go—my job was hardly “essential”—and after having resisted the betting temptation for years, decades really, I got involved in a fantasy wagering pool based on that season’s Saratoga meet. I anted up 75 government-bestowed dollars in exchange for 600 fantasy dollars to wager in any way I wanted. About a dozen other players, some of them quite sharp, as it happened, did likewise. The handicapper holding the most pretend dollars at the end of the action on the Sunday before Labor Day would be declared the winner, the prize being the antes of the other players. Turning make-believe money into cold hard cash—I dug the objective.

I might’ve told you then that I knew the game. I didn’t. I had a vague idea about betting long shots to win, place, or show (that is, finish first, second or third). I’d buy the Daily Racing Form. A considerable investment that horseplayers have been wailing about since time immemorial, the “Form” provides scores of numbers about the past performance of each horse entered in every race at every racetrack in North America that day. I deciphered those figures like I was translating the Rosetta Stone.

Racing luck, beginner’s luck, dumb luck, whatever you want to call it, is an inexplicable force in our universe. You can probably guess which way this is going. The worst possible thing happened: I won. And seemingly overnight, I was a goner. It is no exaggeration to say that over the past three years I have dedicated most of my energy to horse racing. Irish jumpers entered for the boutique meet at Listowel? I’m in. Rock bottom claimers running at bull rings you’ve never heard of? Ditto. Ruminating, calculating, quite literally dreaming about the races.

Anybody laboring under the delusion that there’s easy money to be made at the racetrack is a fool. A rube, a chump, a sucker. Serious handicapping requires sustained concentration. Many of the races on any card are not worth playing, but to discern that—to identify the races that do provide value—is only one component of the handicapper’s challenge. The tough beats far outnumber the big scores, and that’s the nature of the game. I win all the time. Problem is, I lose all the time, too.

I’ve lived in New York City for almost 40 years, but my western New York roots run deep, and whenever I visit Rochester, I slip out to Finger Lakes for a few races to honor and, frankly, cherish family memories. Of Aunt Florrie and Uncle Vin and great Uncle George Barone. Of my dad—no stranger to the venue—and his brother Frank (of candy store infamy) who made much of his living as a bookmaker. And of a rotund reprobate named Jack, a racetrack bum who dated a beloved aunt of mine and, I’m afraid, relieved her of many conscientiously earned dollars.

***

Haunted by the ghosts of a million busted-out horseplayers, one recent afternoon I sat nearly alone in the Aqueduct grandstand. The fog was rolling in off Jamaica Bay. The seagulls cawed in the distance. I looked out over the oval and landscaped infield and wondered: How do I make the rest of my life about this? I might as well write about it, though I’m no turf writer, nor do I wish to be. I’m still compelled by too many other interests, early Christianity, for example. Nashville’s Golden Age. American movies from the 1930s. So, if it sounds like I’m combining two time-devouring, measly-earning (and often, money-losing) activities, and striving to turn them into some kind of profit, that’s accurate. Brilliant, right?

But I don’t want to end on a glib note, and so here I offer a caveat. Maybe two.

An old saw has it that you can beat a race, but you’re not going to beat the races. There’s a “beautiful loser” aspect to the colorful characters at the track, trainers whose barns have gone permanently cold, players who are consistently one horse away from the score of a lifetime, aging jockeys hanging on because they don’t know, and don’t want to know, anything else.

I’m wary of our societal reflex to tag anything we might be enjoying a little too much as an addiction; but gambling is a dangerous pursuit, especially in its all-pervasive contemporary iteration, married to the palm-sized computer in your pocket. The individual, in-game, so-called prop bets—Will Bryce Harper hit a home run tonight? Will he hit two?—are designed to drain your bankroll. And when you cross the threshold into a tarted-up gambling hell, that is, a casino, and the soles of your shoes glide over the marble floors, and you’re admiring the state-of-the-art lighting, bear in mind that those things aren’t there because most of the gamblers who came in before you were winners.

As for the horses, I’ll win a few, lose a few, leave a couple on the table. It’s okay to pass on a race, on an entire card, to take a week or two away from the game entirely. Simply watching the contest among these magnificent equine and human athletes in pure appreciation for the competition is always, repeat, always an option. There will be other horses in other races on other days.