Rob Masiello on the Highs and Lows of the Game

Rob Masiello has been coming up to Saratoga since he was in the seventh grade.

It all started when he went to “nerd camp” at Skidmore College one summer. He was miserable there, missing his usual summer vacation spent playing baseball with his friends. One day his parents came to visit and told him they would take him home if it was what he really wanted, but first they wanted to go to the track.

“We had a great time and I ended up staying,” Masiello recalled. “Then it sort of became a tradition for us to come up every year. Now even to this day when I walk into the track, I always think of being a kid here with my parents and I'm sure a lot of people probably have a similar experience. It's certainly a special place.”

Fast forward to 2005, two years after he graduated from Johns Hopkins with a degree in Economics, Masiello got involved as an owner with West Point Thoroughbreds.

“When I started I had the smallest piece of the smallest horse, but I enjoyed it,” he said. “The cool thing about being with West Point, or any partnership I think, is that you buy into a piece of one horse but you learn about an entire stable. So if you're smart about it, you get to see what's going on with 50 or 60 different horses at any given time and it really gives you perspective on what a stable looks like and what the ups and downs can be.”

Over the years, Masiello has been a West Point partner on graded stakes winners Freedom Child (Malibu Moon), Twilight Eclipse (Purim), Ring Weekend (Tapit) and-the one he now thinks of as his all-time favorite–dual Grade II winner and Grade I producer Justwhistledixie (Dixie Union).

“She was my first good horse,” he said. “I knew it at the time, but I also didn't know just how special the run she had was when she won five straight races ending in the GII Davona Dale S. and the GII Bonnie Miss S. To see what she has gone on to do as a broodmare has just been incredible.”

In recent years Masiello, an Equity Trader for Chimera Securities, has had success in developing his own racing stable. While he remains a loyal West Point partner, he said he is enjoying the challenges that going solo has presented.

“It's been a lot of fun and it's a lot harder,” he admitted. “It's a different skill set because with West Point, they're basically buying the horses they want even if they're seven-figure horses. I can't really do that on my own, but it's kind of fun this way too because you really have to think about your budget and what you're trying to achieve. It's a little bit more strategic thinking.”

Earlier this month, he made it to the winner's circle with a five-year-old mare he bred and now races in partnership with trainer Tom Albertrani. Itsakeyper (Brilliant Speed) got her first win against allowance company at Saratoga on Aug. 12.

“Tom and I actually claimed her dam, Finders Key (Discreet Cat),” Masiello explained. “She was a horse that Tommy trained for Godolphin that got claimed away, but he had always wanted to try her on turf. The funny story with her is that we claim her and then go with Twilight Eclipse to Dubai [for the 2014 G1 Dubai Sheema Classic]. Tommy lived in Dubai for several years and trained there so bringing a horse over to Dubai was special for him, but all he wanted to do on that trip was talk to me about Finders Key. At a certain point I was like, 'Tom, what are we talking about right now?' We were there with Twilight Eclipse and all he wanted to talk about was the $25,000 claimer we had.”

Finders Key made her first start on turf for the duo a winning one, but an injury forced her to retire soon after. Masiello and Albertrani sent her to another Albertrani trainee in GISW Brilliant Speed.

That first foal, Itsakeyper, didn't break her maiden until May of her 3-year-old year, but Masiello said their homebred is just now reaching top form.

“She has always trained well, but she's gotten better and better as this year has gone on. Tom was really happy with her coming into the race [on Aug. 12] and it's special because he trained the mare and Brilliant Speed, so it's the whole all-in-the-family thing. Dylan Davis gave her a perfect trip. A lot of times you come up here and nothing works out, but everything that day just worked out perfectly.”

On the flip side, Masiello knows all too well how things in this sport can go from perfect to disastrous in the blink of an eye.

On July 31, Fiya (Friesan Fire), a $400,000 purchase for Masiello that had gone on to win four of his next five starts for his new owner, was training at Saratoga in preparation for the GIII Troy S. when he suffered a catastrophic injury and was subsequently euthanized.

Reflecting on the loss, Masiello said he thinks of Fiya as the horse that got his racing stable off the ground.

“I remember the morning of his first race, I was walking around Battery Park City where I live and I had really not been doing well as an owner on my own,” Masiello recalled. “I looked on the NYRA website and was winning at two or three percent and I didn't know if I could handle another horse that didn't work out.”

Fiya takes the 2020 Claiming Crown Canterbury S. | Lauren King

But Fiya did win that first race for his new owner by over three lengths and would go on to claim the Maryland Million Turf Sprint H. and the Claiming Crown Canterbury S. later that year. Trained by Tom Albertrani, he was 11^th this spring in the GII Twin Spires Turf Sprint S., but came back with a victory in his last start in an allowance at Belmont.

“He was a very talented horse,” Masiello said. “Every race he ran in was a special experience for me. Even the one race he lost was awesome, too, because I took my dad and my uncle out to the Kentucky Derby when he ran in the Turf Sprint on Oaks Day. I'm incredibly grateful for that.”

Masiello said this was the first horse he and Albertrani have had suffer a catastrophic injury together and spoke on the struggles he has worked through since the accident.

“It was very difficult. He was a very special horse for me. There's no question in my mind that my stable before I owned him and after I owned him are two different stables. Everything started clicking after I bought him. From an ownership side of it, yeah it's tough losing him, but having to put him down is really what's been the struggle over the last couple of weeks.”

Masiello is using this tragedy to throw his efforts into his position as a New York Thoroughbred Horsemen's Association board member.

“One of the things I've tried to do as a NYTHA board member is look at the bigger picture and how we do as an industry to focus on getting those numbers lower over time,” he noted. “I think it's important as an industry that we keep going with what are the best practices we can do to make sure these sort of things are really just freak accidents and not something that's systemic.”

Masiello said he has taken several lessons away from his experiences, both good and bad, with Fiya.

“He changed where I was at as an owner,” he explained. “People think that just because you spend 'x' amount of dollars, you're going to get a good horse. That's not how it works at all; I can verify that quite substantially. I think the one thing I learned from him is that I'm not afraid to fail. When you're spending a lot of money on a turf sprinter, you're a little exposed. If that horse doesn't work out people are going to mock you a little bit, but that's part of the game and it's part of sports. I think as an owner, you have to say, 'I accept that I'm going to fail sometimes and I'm not afraid to come back and do it again.'”

Masiello is an outspoken advocate for an owner's responsibility in improving the sport by making the game cleaner.

“I'm not going to sit here and pretend that I know exactly every single medication that every single horse I own gets,” he explained. “It's not my expertise and it would be taking me away from things I really am productive at for me to have a million questions. But what I can do as an owner is say to my trainers, 'I'm with you and I'm not going to pull horses if we're winning at less that 10%, but on the flip side I want to run a clean, honest stable.'”

Rob Masiello and Joe Migliore celebrate a new purchase at the Fasig-Tipton Sale. | Fasig-Tipton

He continued, “I'm up here to have fun. I want to win and be competitive, but there's a right way to win and a wrong way to win and I don't want to be caught up in any of this stuff that unfortunately a lot of people in the industry are in. I think it's as simple as telling my trainers that I'm there for them through the good times and the bad times and that we're in this together for the long term. That has always been my perspective as an owner and I think it's important to get that message out.”

One key relationship that has already fostered many trips to the winner's circle for Masiello is his friendship with Joe Migliore. The up-and-coming young bloodstock agent had a hand in the purchase of Fiya last year and has since picked out several promising horses for Masiello.

Masiello compared his friendship with Migliore to that of one of his mentors, Terry Finley, with trainers Dale Romans and Dallas Stewart.

“They all came up together and built something together and to this day, Terry sends a lot of horses to both Dale and Dallas. Terry has so many good relationships in the industry, but the relationship he has with those two is special. I feel like Joe and I kind of have the same thing now where we've been through it together-the highs and lows, the horse that didn't work out and the horse that did work out. It's so much more fun when you're doing it with people you love and respect and I think that's what we have together.”

As Masiello continues to up his game in the sport, he already has an image in mind of the owner he hopes to be seen as based on a few industry members he has looked up to over the years.

“I happen to have a box right next to [LRE Racing's] Lee Einsidler,” he said. “You see him floating around the boxes up here and he's just so happy and supportive of people. He was the first person to text me last week when I won. I also see that a lot from Tom Bellhouse, who works for West Point. He's always a guy that comes off to me as someone that is always so happy to see other people do well. We're all a big family in this industry and I hope people know that I like seeing good people do well. I think that's something I've learned a bit from Lee and Tommy.”

“The biggest thing I think I want to be thought of as an owner is that I'm just happy to be here,” he explained. “I'm competitive. I want to win. But I also know the struggle we're all going through as owners because it's a tough game. I just like being up here and I like being happy for people.”