I Spent The Weekend Betting Horses With Dave Portnoy

Saratoga Springs, New York. A town plucked from another era, thrust with all its parts into a time machine, and altered in appearance only. Strolling down Broadway, I was drawn to the magisterial façade of the old Adelphi hotel, the clocktower that kept time for inattentive visitors, and the power lines that criss-crossed the street like an electrified game of cat’s cradle. I half-expected to see Marty McFly zoom past in the DeLorean, disappearing at the end of a pair of garish skidmarks.

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I was in town for a bachelor party. Those in our group who were unfamiliar with Saratoga had voiced their dismay over the choice of locale. “Saratoga? What is there to do in Saratoga? We should be going to Vegas,” said the uninitiated. I knew better. I had been to Saratoga in the winter for some standup shows, but the town assumes an entirely different character during August weekends. Thousands of visitors flock in to see the horse races at the venerable Saratoga track, donning their finest hats and bow ties and all manner of haberdashery. Distinguishing a glaring class divide, others wear grey t-shirts and stained cargo shorts with their ankle fat spilling over the sides of their bursting sneakers. These “people” (I use that term loosely, with great disgust) typically plop into canvas lawn chairs in the “picnic table area,” outside the track, to watch the races on televisions erected for their drooling, sedentary pleasure. They stuff their mesh cupholders with plastic-wrapped ham sandwiches that even the airlines wouldn’t serve, park themselves among the pine trees, and settle in to place minimum bets throughout the day, pretending they’re worth more than their faltering, arrhythmic heartbeats. Why such a classy event needs to be made available for such lowlifes, such molluscs on the underside of society’s rotting log, I’ll never know.

Fortunately, we of the higher order had paid the crippling ticket fee of ten dollars–TEN DOLLARS–to gain entrance to the club house. As we passed under the overhang, an excited buzz sparked from one man to the next. Eager patrons placed their bets to stalwart tellers with the help of handicapping sheets. Small groups of informed enthusiasts whispered tips to one another, holding their edges close to the chest. Longshots were considered but largely dismissed; the names of jockeys and trainers were dropped to show an insider’s knowledge. I withdrew $400 and handed my debit card to a friend-turned-guardian, with the express direction that he should not, under any circumstances, relinquish the card to me before we’d left the grounds. In the face of great loss, my willpower dissolves.

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I did my best to focus on the races, but I was distracted. Not by the beautiful women in their race-day dresses, nor by the handshakes and approving nods from the many fans who said that they enjoy my work despite hating me personally. I had my eyes peeled for one man, and one man alone: my friend, Dave Portnoy.


My friendship with Dave is not without complication. Last winter, we forged a foundation through repeated hangouts over Christmas break. Then, just a few weeks later, we reinforced our bond in the nightclubs of Miami. At the end of that month, I thought that only an act of God could stop us from spending every weekend together for the rest of our lives. But every dance must come to an end, and slowly, our rendezvous ceased. As winter turned to spring, Dave refreshed his inner circle with a far younger cast of cherubic, acquiescent pawns. “Out with the old, in with the virgins,” seemed to be the guiding principle. Tommy Smokes and 15-year-old Steve saw their stock soar as Dave sent my tired, broken ass to the glue factory without so much as a gift certificate. Tommy even in moved in for a spell, turning Dave’s apartment into a playhouse for the second mile.

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During this time, I lost myself. I spent a lot of time in sex shops, reading the back covers of obsolete pornographic DVDs and donating huge portions of my salary to the Clinton Foundation. I spent a night sleeping in Central Park to understand the mindset of squirrels. I would loiter outside ice cream stores and spike the freshly-scooped cones of happy children to the ground, run away before their illegal nannies could learn enough English to raise the alarm, and watch the tears unfold from the safety of a nearby parking garage. Losing Dave had a profound affect on my daily routine.

But the darkest hour is just before the dawn. Rescue came in the form of a bachelor party that coincided with a weekend Dave was also heading to ‘Toga. I didn’t know that he was heading up there until Thursday. “Where’s Dave going?” I asked Frankie on Thursday, as Dave left the office. Frankie put down his copy of “I’m A Tomboy, But I Still Like Guys” and told me Dave was headed to the very place I was going in just 24 hours. I couldn’t believe it. I walked quickly and quietly to the bathroom, ripped off a few sheets of toilet paper, and placed them in my mouth as a gag to muffle my screams of joy. We were back on.

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So there we were on Saturday, at the race track, with the world at our fingertips. I texted Dave the following:

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Ignore the unrequited text I sent on July 22nd. That was a huge mistake by me. I hadn’t seen Dave in a month and I was losing my mind. This was probably the low-point of my dark time. But as you can see by the fact that he responded at the race, we’re totally cool again. I add a lot of value to his life. He likes having me around. I’m “one of the guys.” I’m not someone who sits by his phone, waiting for a response from his boss, feeling like the time between my text and his response is elapsing in dog years, each second multiplied by factors of seven.

Off I went, jog-walking from one end of the grandstand to the other, maniacally tucking in my shirt, fixing my collar, stopping in the bathroom to throw up the four beers I’d had so that I could look more toned, and banging out a quick set of 50 dips on the toilet seat to bring out the horseshoes in my triceps in keeping with the equine theme of the day. Of course I washed my hands afterward–something told me Dave and I would clasping hands in victory soon enough.

On the way, I ran into a road block. Office Manager Brett and Matt Brown were also at the races. Normally, I like these guys a lot. But on that day, they were an unnecessary hindrance, a complication on the Portnoy Friendship Expressway.

“Dave is here too!” offered Brett, as though I wasn’t already texting with him.

“I’m already texting with him,” I said, letting Brett know how much closer I am with Dave than Brett is. Then I looked at Matt Brown and sniffed.

“Hey Matt,” I said with a sneer. “Are you texting with Dave?” I added, with a chuckle.

Matt looked at the ground. “No. He doesn’t even email me.”

“Oh, that sucks man. Well, keep selling ads. Maybe someday, I’ll send you his number.” I walked off, grinning at how well I had clarified my superior standing with Dave. There could be no doubt. Had Matt and Brett lost their heads and run out onto the track to be trampled by a stampede of galloping horses, Dave and I would have cheered together.


Putting the losers in my rearview, I continued on towards Dave’s box. Because I was checking the rows, looking for A6, I didn’t see Dave walking towards me until we were standing just a few feet apart.

“Hey Francis,” he said.

He wore a blue sport coat, blue tartan trousers, tan oxford shoes, and a light blue tie. He looked like the sky between the clouds on a sunny day. Not since the Golden State Warriors added Kevin Durant has an ensemble come together so completely. Perfectly tan from his time in Nantucket, perfectly cool despite the humidity of the day, and perfectly at home at the race track, Dave was the portrait of a gentleman–exactly the type of man you’d spot at the races and think, “what hasn’t he accomplished?”

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“Dave!” I stammered. We exchanged a few pleasantries. He mentioned to his friends that a lot of Barstool people were at the track that day, including Brett and Matt Brown. This sucked for me, because he was clearly lumping me in with the non-factoring pawns that work for him. I understand that technically, I work for Dave. But friendship transcends the bonds of employment, and I had thought Dave would introduce me in kind.

Soon, he asked if I wanted to come check out the box. At least, that’s how I remember it. I may have invited myself. Either way, we went back to his seats. There, strawberries floated in champagne flutes filled with vintage, golden bubbly. A server was summoned with a condescending snap of the fingers. Neighboring boxes leered at our small group, wondering how God could have assembled such a fine collection of his children. We talked, we laughed, we lived not just our best lives, but the best lives that humankind could offer. We lived for the sake of others, to provide a model for how things could be. And just for a moment, as the sun reached its zenith, our box looked for all the world like the Garden of Eden.

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I followed Dave to the betting booth. He placed his bets, and I followed and told the teller that I wanted to place the exact same bets. It was an exacto box that combined the 5 and 6 horses, and then an outright bet on the 6 horse to win. Dave knows how to pick a winner, and I know how to pick a best friend. With our tickets in hand, we went back to the box for the race.

As the horses burst forth from the gate, we all leaned in to the rail for what would become the most exciting two minutes of my life. The 6 horse steadily kept pace in the middle of the pack, but the 5 horse lagged behind for the first half mile, and all appeared lost. I assumed I’d lost my $100 exacto bet, but all friendships require sacrifice. “The six looks great,” said Dave. I nodded in agreement, afraid to speak. As the horses rounded the bend and came into the stretch, the 5 horse started to creep back into the picture. “Here he comes,” said Dave. You could feel the hooves pounding the turf as the crowd rose to its feet. The 5 was making up ground in a hurry, passing the first of the middle pack. Simultaneously, the jockey on the 6 horse was making a move. He shot towards the front and took the lead with less than a quarter mile to go. By now, I was screaming. I had completely lost my composure. The women in our box looked at me in disgust, but I was totally consumed by events unfolding on the track. The 5 horse was surging, his jockey urging him onward, showing him the whip. As they thundered down the track, I started to piss myself. Spittle flew from my gums as I foamed at the mouth, channeling the horse within me. With 50 lengths to go, the only question was whether the 5 horse would overtake the 6. But the 6 held on and they crossed the finish line just a few heads apart, turning our tickets to gold. At some point, I had Dave’s hand, and I screamed “we’re rich! We’re fucking rich!” He did not like that because he is already rich. A young lady asked how we had done. “This was good for us,” said Dave. “But I don’t know about all that ‘we’re rich’ business.” Everyone laughed as I slunk into my seat, exhausted, slightly embarrassed for having revealed just how little I had “been there before.”

After a minute, I thanked everyone for having me. I know better than to overstay my welcome, even though I wanted to stay all day and then take an uber with them somewhere after the race, and then have an after-party somewhere, and then maybe dinner, and then talk for a few hours before bedtime, when I’d throw an air mattress at the foot of Dave’s bed and we wouldn’t say goodnight as we nodded off to sleep, breathing the same air, because there was no need to state the obvious–a good night indeed, to end the best day ever.