VIP for a Day: Betting the Derby With a Table Full of Millionaires

VIP for a Day: Betting the Derby With a Table Full of Millionaires article feature image

The Highlights

  • Paul Lo Duca and I went to an OTB on Long Island called the Race Palace for the Kentucky Derby.
  • He introduced me to his group of horse racing friends, including Mike Iavarone, the owner of 2008 Kentucky Derby winner Big Brown.
  • These guys have a lot of money; I do not.

Coming into the Kentucky Derby, I was on an epic cold streak. Let’s just say March Madness and the Masters treated me like foreign water treats a tourist, and I was still trying to punch my way out of the slump by the time the first Saturday in May came around.

It just so happened that I would be spending Cinco de Mayo in the company of my Action Network colleague Paul Lo Duca and two of his friends, one of whom happened to be Michael Iavarone, the owner of Big Brown — a horse that fell one race shy of the Triple Crown in 2008. There’s never a good time for a cold streak, but enduring one leading into one of the biggest gambling holidays of the year — and then spending said holiday at the millionaire table in the VIP room of a Long Island OTB — that’s cruel and unusual timing. Should I have taken the day off from punting? Probably. But who are we kidding, I don’t have the self-control necessary to not have Action on a day like this.

My Kind of Place

All week, Paul and I were working out where we wanted to watch the races. We wanted to be at a place where we could shoot a quick video so he could send out an update to his followers. We tossed around a couple of ideas, including getting a spot at Belmont, before settling on the Race Palace — a massive OTB in the middle of Long Island.

As a proud Long Islander and former bartender at a gambling haunt, I was a little ashamed that I had never heard of the Race Palace. Paul spoke highly of it. And when I say he spoke highly of it, I don’t mean in the way someone glows about a fine-dining institution, but more like the way you sound when you’re trying to convince your friends that the dive bar you ended up at last night wasn’t that shady. I could tell from his description that this was my kind of place.

As my Uber driver turned onto Round Swamp Road, I caught a glimpse of the place, and my ears involuntarily pulled back to allow a giant smile to flow across my face. The Race Palace was majestic. There was this weird antenna thing on the top of it, and the entrance made you feel like you were about to go see “The Sting” or “Deliverance.”

I didn’t know what to say or where to go to find Paul, so I took in the sights for a moment. The carpeted floors and private gambling booths gave this place a Vegas-style feel without it being forced. The floor was alive with Long Island’s thickest accents. I was in heaven.

Most of the time, these places stick the VIPs and high rollers upstairs, so I ascended up a set, expecting someone would stop me, as I looked like a fish out of water with my backpack and Everton jersey on. I was well-aware of how ridiculous it would sound when I did eventually get stopped that I was here to watch the races with a very popular former New York Met in the heart of Mets country.

I did eventually get stopped by a man who looked — and sounded — exactly like you’d imagine for someone working the VIP room at a place like this. He was an old-timer wearing a vest and a tie that looked like it had seen some things. I told him who I was looking for, and he didn’t skip a beat.

“Paulie? Oh no, you don’t want to be messing with that guy,” the usher said. “He hasn’t picked a winner here since I met him.”

With a laugh, he pointed me to a door and said I would find Paul and his people in that room. In I went and off we went.

My Kind of People

As soon as I entered the room, Paul introduced me to his friend, Mike Iavarone, and his wife Jules. I tried to keep my poker face, but I was a bit gun-shy at first given the company. But my new friends couldn’t have been warmer.

There’s something beautiful and comforting about brick-and-mortar gambling shops. We live in a world where you can bet on anything — and I mean anything — from anywhere, as long as you’re connected. But to be inside a place where gambling is part of the fabric and not kept to the shadows allows everyone to let their guard down. And just like that, Paul, Mike and Jules were telling me about the Palace and its characters.

There was Freddy Carvel, a degenerate who made his money opening ice cream shops around the island, and there was Doc-Lock, who used to spend 364 days at the Palace but now spends 365 days there.

I like to think of myself as an affable guy, one who is easy to talk to, but introductions become so much easier when you have something in common with new people. For us, the common thread in our friendship quilt was gambling. When I found out Jules was from Texas, she spoke about rodeos. The first question that I asked, which probably would have raised red flags in any other setting was, “Can you bet on the rodeo?”

“You’re my kind of guy,” Iavarone said.

I never got an answer about the rodeo, though.


Rip Shots, Not Tickets

I don’t consider myself much of an expert when it comes to the ponies. Thanks to my days at the aforementioned dive bar, I could talk shop, but when it comes to picking winners, you should run away from me. Far away.

The people I was with, however, they knew what the hell they were doing.

My plan going into the day was to tail Paul’s picks, but his bankroll reflects the fact that he played in the major leagues for 10 seasons, while mine reflected the fact that I odd-jobbed my way through my mid-20s. I stuck with his basic game plan, but tweaked things to stay within my $100 budget for the day. While I was fiddling around with $4 dollar exactas, these guys were putting crooked numbers on 10-1s as if it was nothing. At one point, Mike placed a bet through his app on a horse in an undercard race, and we watched as the line dropped. While he was moving the market, I was staring at my $16 “to win” ticket on Untamed Domain (he didn’t win) trying to figure out how I ended up in this absurd, but wonderful, situation.

Race after race, no winners. Not only for me, but for the entire table. I did worry that the temperament of the room would change as the pile of ripped-up tickets grew larger, but it never darkened. In fact, with each passing minute, the company got better, and so did the stories.

Paul shared a story about how he holds the record for most passed balls in a Double-A game (it was very cold in Wichita that day, he couldn’t feel the ball hit his glove), and Mike was telling us about the time he witnessed Joe Pesci*, basically in character, floor someone at a race a few years back. He also told an absurd story about how he couldn’t get a line on NASCAR’s version of the All-Star Game, so he flew to Las Vegas, placed the bet, and then flew to North Carolina for the race. He won.

The Sports Pope

As we swapped stories, we began to talk about Matt Harvey. Paul’s thoughts on the situation were clear, and I brought up a great Mike Francesa rant on Harvey from a few years ago.

“He’s going to be here soon,” Paul said. “He sits right over there.”

Not 10 minutes later, there was the Sports Pope, scribbling notes in his Racing Form at a nearby table. As the creator of a Mike Francesa Convention, I had to pay my respects to the King.

“Sonny Gray looks like he’s turning the corner, Mike,” I said.

“He looked all right,” he replied while fidgeting with the television.

There was nothing else I had to say.

“All right, Mike have a good day.”

“Good luck with everything,” he said in a “why does this guy keep showing up, can’t he just leave me alone?” kind of way.

With that, I was on my way back to the high-roller table — but not before a pit stop at the brownie station of the VIP buffet — ready to donate more of my hard-earned money to my new favorite place on earth.


The Best 0-fer of My Life

As Yoshida, a horse from Japan, upset the field in the Turf Classic (the last race before the Derby), I realized I was down to my last $21. On a normal gambling picnic, I’d be salty with how poorly I was faring, but this was entering too-good-to-be-true territory.

The group, which now included another superrich guy who was pleasant as can be, was talking strategy for the Derby.

“I’ve got no idea how to play this,” Iavarone said.

His sentiment was echoed by the room, and I just nodded along, knowing full well I was going to put my last dub on Magnum Moon — the horse that Paul liked.

While the lot of them were tossing around outrageous numbers, I sat there making sure I counted my money correctly. Two fivers and 11 singles. In relative terms, those $21 felt more like $5,000 given my budget (give me a raise, Millman), so I didn’t feel like I was at the kid’s table.

As the race went off, I don’t think I heard Magnum Moon’s name once. In fact, Paul knew within like five seconds that Justify was going to win. We kind of just watched in amazement as this horse effortlessly blew by the field and past the finish line.

With that, my day was over. It was back to the part of my life where I’m not kicking it with multimillionaires sharing stories about 77-foot yachts and running into the Dallas Stars at a club in Mexico.

Even though I didn’t get to the window once, I felt like my slump was broken. Probably not, though.

Photo credit of the Race Palace.

*Joe Pesci, if you’re reading this, please don’t kill me.