Masiello, 33, Enjoying the Ride With West Point

The Life

Rob Masiello and wife, Skye, at the 2014 Preakness Stakes, where West Point Thoroughbreds' Ring Weekend finished fifth. (Photos courtesy of Rob Masiello) 

It all started for Rob Masiello with a little curiosity, an email and a return phone call.

Ten years later, horse racing has taken him across the globe and back and twice to the Preakness starting gate.

Masiello is 33 years old and has owned racehorses for 10 years. That’s almost unheard of in Thoroughbred racing unless the owner comes from a racing or royal family.

Masiello fired off a spur-of-the-moment email when he was in college at Johns Hopkins in Baltimore. A commercial for West Point Thoroughbreds that he’d heard many times on WFAN sports talk radio during him commute to and from Baltimore and his hometown of Oradell, N.J. sparked the interest.

West Point founder Terry Finley called him back 10 minutes later and they talked for half an hour about partnerships, even though Masiello told him he was in school and wouldn’t have the money to invest until at least a few years after he graduated.


Masiello had been a casual racing fan since childhood and his passion for racing slowly built while at Johns Hopkins, where Preakness Stakes buzz blanketed the city every May. That half-hour phone call with Finley planted the bug.

“I thought, ‘This is pretty cool; this guy knows what he’s talking about and he’s got a good grasp on the business,’ ” said Masiello, now an equity trader for Chimera Securities. “What I said to him was, ‘Look I’m in college now, but when I get out of school, if I get a good job, I’d definitely be interested in investing.’ ”

In 2004 with a full-time job and some money in his savings account, Masiello took the plunge and invested in racehorse ownership with West Point for the first time at the age of 24.

“I bought a small percentage of probably the cheapest horse they had when I started, and 10 years later I have 20-something horses with them,” said Masiello, who is a partner in 2014 Preakness fifth-place finisher Ring Weekend. “I’ve grown as a client and [West Point] serviced me great when I was literally the smallest client that they had. As I’ve grown, they have still been able to provide great customer service for me and they’ve been able to meet the needs that I am looking for, which have changed over the years.”

Masiello has discovered that a racehorse can take you pretty much anywhere in the world – he went to Dubai this year to watch Twilight Eclipse compete in the Dubai Sheema Classic – but he’s also learned how humbling the game can be.


While racing provides the highest of highs, he said new owners have to be prepared for the valleys as well. Success in Thoroughbred racing rarely comes right away.

“If you want someone young that’s going to be in the game for a long time, you have to set the expectations low, because it’s hard,” Masiello said. “I’ve been involved in horses that I thought were going to be stars that never made it to the races or horses that flashed a ton of talent and then got injured and were never the same. It’s hard, but again, and I mean this sincerely, when it does go right, it feels so good.

“It’s so much more rewarding when you’re invested in a horse and you get to watch the horse grow up and they do succeed and they do get to the highest levels of the sport … and it can happen. I mean look at our sport right now. Everyone is talking about California Chrome and that’s a true rags-to-riches story.”

Masiello, of course, is referring to the success owners Steve Coburn and Perry Martin enjoyed with California Chrome, their very first homebred who went on to win the Kentucky Derby and Preakness Stakes.

“The biggest advice I would give to a young owners is just to stay patient,” Masiello said.

Masiello’s very first winner was an exercise in patience. Precocious Penny was a West Point purchase in March 2005. It took six starts, 15 months and two trainers before she got her first win in June 2006 at Woodbine. It was worth the wait.

“My wife [Skye] and I had gone to England, and that was right before you could get information on your cell phone; it was in 2006 so it was right before you could whip out your cell phone and see what happened,” Masiello said. “I remember being in London and trying to find an internet café to see who won the race. But when we found out it was just like, it sucked that we weren’t there for it but it was just a night I’ll never forget. We went out and celebrated and we were taking shots of Jack Daniel’s.


“That’s over a year of waiting for just one win. Some people just can’t handle that. … In horse racing there is no guarantee that your horse is even going to run. The upside of when they actually do win and you know how hard it was … it’s special.”

Masiello is a big sports fan who played some college baseball and enjoys a round of golf. He and his wife also love traveling, and that has been part of the allure of owning racehorses.

He went back to Baltimore in 2011 and 2014 for the Preakness Stakes, finishing seventh with King Congie in the former and fifth this year with Tampa Bay Derby victor Ring Weekend. But the Dubai trip in March with the group of West Point investors who own 4-time graded stakes winner Twilight Eclipse really stands out for the Masiellos.

“What was cool about that was, I think 12 total partners went out, including their families, and [trainer] Tom Albertrani went out with his family and the Finleys went out and a couple of the West Point employees went out,” he said. “It was like being a kid again and going on a trip with all of your friends. We did a couple of things in the city and then we did a Safari on Friday night. Tom Albertrani trained over there for a while and both of his daughters were born there, and then they left in 2003 or 2004, so he hadn’t been back in like 10 years, so it was just cool to see how excited he was to be there.”


For Masiello, it is the thrill of victory that separates racing from other sports. A big fan of the New York Rangers, Masiello savored every minute of the team’s run to the Stanley Cup Finals. But even something like that can’t compare to owning part of a winning racehorse. Masiello pointed out that even the worst baseball team wins 60 games a year, but many racehorses never even make it to the racetrack.

Masiello said the reward for patience is well worth it. He fondly remembered a victory by a horse who won for only the second time in a low-level allowance race on the grass.

“It was a big partnership and you would have thought we won the Breeders’ Cup Classic — I mean, people were going nuts,” Masiello said. “It’s a hard sport; it’s supposed to be fun.”

Masiello got his first taste of horse racing in the summer at Saratoga with his family. He started taking classes as a seventh grader at Skidmore College in Saratoga Springs, N.Y., and when the summer session ended he and his parents stopped by the Spa for an afternoon of races before heading home. It became a yearly tradition.

The experiences he and his wife have enjoyed with West Point have a similar feel.

“The Finleys at this point have become like family. Terry’s daughter got married on [June 14] in Lexington, and I was actually out there. I can’t say enough positive about them. They have been awesome,” said Masiello, who also was a partner in multiple graded stakes winner Justwhistledixie. “There are a lot of good partnerships; I’m not trying to knock them. I just have a very strong relationship with Terry and his family and all of West Point, really. It’s been a really great relationship that we’ve had for the last 10 years.”

Interested in learning more about how to become a racehorse owner? Learn more about the thrills and excitement of owning your own racehorse or joining a partnership or syndicate at:

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