One could not have faulted Anthony Mattera if, at some point, he had decided to never play in a HorseTourneys major event again. It’s not that the 40-year-old legal consultant in Palm City, Fla., did poorly in these big-money competitions. Quite the opposite. It’s just that they had a way of dealing Mattera some setbacks that would have challenged the resolve of even the most determined horseplayer.

In the 2023 Players Championship, Mattera held the lead late only to lose by $4.86 to Lucas Van Zandt. The $4.86 deficit cost Mattera $92,000.

That near-miss was nothing compared to what Mattera experienced a couple of years earlier.

In the 2021 Flo-Cal Faceoff, Mattera was in front with one race left when a 29-1 shot took the contest finale and dropped him to 3rd place behind winner Alan Levitt. This late reversal of fortune cost Mattera $164,000.

Three months later, Mattera came in eighth in that year’s Players Championship. 

Then in the 2021 Spa & Surf Showdown, Mattera led at the conclusion of Day 1 by more than a cap horse ($72.00 to be exact). He wound up finishing fifth and settling for $45,000 instead of the first-place prize of $235,000. (The three top-10 finishes comfortably earned Mattera top honors in that year’s HT Tourney Triple Series.)

Fast forward to last weekend’s $300,002 New York, New York Challenge. After a strong late rally at the end of Friday’s Day 1 of this two-day Pick & Pray test, Mattera again found himself on top of the leaderboard by a pretty sizable margin.

Then, in the first two Saratoga races on the Day 2 card, he added $16.80 and $19.20 winners to his total.

Watching that second Saturday race go official while onsite in Saratoga’s 1863 Club, Mattera knew he was in a very good spot, but a short time later, a friend who was keeping tabs on the New York, New York Challenge stopped by. He slapped Mattera on the back and said, “You got this!”

Perhaps the friend wasn’t aware of the backstory. In any event, Mattera stopped him dead in his tracks. 

“It’s not over!” Mattera insisted, his facial expression suddenly turning serious.

As it turned out, though, the friend was right. This time, there were no excruciating punches to the gut at the end. No more “close-but-no-cigar” unhappy endings. No one could catch Mattera the rest of the day, and he finally had the first-place finish that had eluded him so many other times. He won the top prize of $107,750 — plus an additional $7,480 for having the best Day 1 score on Friday — for a total of $115,230.

“It was so great to get the monkey off my back,” admitted Mattera, who also finished second in this year’s Pegasus World Cup Betting Championship.

For Mattera, playing — and winning — is always a family affair. When he’s competing in an on-track contest like the Pegasus or The BIG One, his wife Julie is seldom far away. That was again the case last weekend when she along with their 10-year-old daughter Adriana and 3-year-old son Ace were there in the 1863 Club to cheer Anthony on.

“My wife is my biggest supporter. She’s the reason I’m able to win,” Anthony said unabashedly. “She knows the roller coaster of emotions involved, and she supports me through all of that. I want to win for her and the kids more than I want to win for myself.”

After his exhilarating triumph, Mattera treated his family and a large group of friends to a victory dinner in town…but not before an even more important moment of commemoration.

Not present in Saratoga, but frequently in touch via phone, was Anthony’s father Gene. Growing up in Ventor, N.J., very close to Atlantic City, young Anthony loved going with his dad to Atlantic City Race Course.

Anthony’s mother wasn’t always keen on Gene’s horseplaying, but Anthony totally enjoyed it…even when he and his father lost. 

“Some nights we’d take a limo home from the track,” he chuckled. “Other nights, we’d literally walk home along the side of the A.C. Expressway.”

There are times these days, though, when even Anthony has to keep family at least a little bit at bay during the heat of battle.

As Day 2 of the New York, New York Challenge went on, Anthony’s focus began to shift from his own horses (all obviously chosen hours earlier) to the ones who could do him damage in the tournament. Before the Met Mile, he let a few people—including his dad via text—know that things would get uncomfortably tight on him if Raging Torrent won. Sure enough, that horse did win at 8-1, and suddenly Anthony worried that his past contest history was getting ready to repeat itself.

“Wouldn’t you know, just then I get a text from my dad all excited because he had hit a $1 super with Raging Torrent on top,” Anthony laughed a couple of days later. “I couldn’t take it. I had to block him for the next three hours!”

One person who Mattera would never think of blocking is his good friend Rich Averill, who was there with him at Saratoga. Averill and Anthony’s “ATM Racing” have owned several horses together (including a few with Jayson Werth), but they love playing the races every bit as much as owning.

“He has been a real mentor to me,” Mattera said. “I try to be a sponge and learn from as many smart players as I can, but Rich is the best bettor I’ve ever known. He’s just so good at structuring tickets, pressing when he’s doing well, things like that. When the contest was over and I won, I could tell he was proud. And that made me feel good.”

Here’s how the two days went for Mattera:

And here were Saturday’s top scorers:

The four Saturday Day Money winners list reads like a Who’s Who of HorseTourneys players this decade. Randy Miller won the 2021 Spa & Surf Showdown. Tim Hughes took the 2022 edition of the Spa & Surf. Ed Peters was the 2023 HT Tour champion and Dave “Gambling Actuary” Nichols currently heads the the 2025 HT Tour standings. 

Then there are the 2025 HT Champions Series standings.

Nichols, Hughes, Miller, Peters and Mattera are now all in the Top 10 behind leader Mike Gillum (6th in the New York, New York Challenge) with two events to go.

As for the monetary payouts behind Mattera in the New York, New York Challenge, Nichols won a total of $47,573 because he finished second in the overall standings. Hughes collected $16,904 in all as the fourth-place finisher across the two days. Rick “I-65” Broth ($21,542) reported home in third position, while Jamaal Barnett ($14,211) rounded out the top five after finishing Day 1 as the fourth-highest scorer.

The money is nice, of course. It’s the main reason why we play. But it’s not the only reason. 

On Sunday, during the return trip to Florida, Anthony Mattera had a running gag with his 3-year-old Ace where Anthony would ask his son, “What did we do yesterday?”

However many times Anthony asked the question, the answer from Ace was always the same: “We won!” The response pretty much summed up his father’s feelings as well.

“It just got to a point with me that if I were in a contest where the winner got $50,000 and a trophy and second place got paid $100,000, I would want to finish first,” Anthony admitted.

“I just really wanted the trophy.”

Sit tight, Anthony. The trophy is finally on its way.