Out of the Gate with ... Rob Masiello
Rob Masiello is an equities/derivatives trader for Chimera Securities who became involved in Thoroughbred racing shortly after he graduated from Johns Hopkins University. Masiello, whose passion for racing started with regular trips to Saratoga Race Course with his family, bought into his first partnership with West Point when he was 24. Masiello has been a partner in standouts such as Breeders’ Cup Turf runner Twilight Eclipse and Tampa Bay Derby winner Ring Weekend. He and his wife Skye enjoy traveling (especially race-related travel) and cherish the friendships created by the ownership experience with West Point.
Name: Robert Masiello
What I do for a living: Equities/derivatives trader for Chimera Securities
How and when I was introduced to Thoroughbred racing: Taking summer classes at Skidmore College in Saratoga [Springs, N.Y.] growing up. My first year there I was pretty homesick, so my parents came up to visit from New Jersey. They took me to the track and by the end of the day I never wanted to leave Saratoga!
My favorite racetrack: Saratoga Race Course
My favorite Thoroughbred racing event: I've really enjoyed the Breeders’ Cup being at Santa Anita Park the past few years, but there really is nothing like a Triple Crown race. I'll go with the Preakness because I went to college in Baltimore.
What I would like to see more of in Thoroughbred racing: New owners
What I would like to see less of in Thoroughbred racing: Negativity
Three words that define what Thoroughbred racing means to me: Friends and family
First Thoroughbred track I ever attended was: Saratoga
Favorite all-time Thoroughbred: For horses I've owned - Justwhistledixie. She was my first really good horse, so I'll always have a soft spot for her. After breaking her maiden, she won four straight stakes races at four different distances, including the Davona Dale and the Bonnie Miss (now the Gulfstream Oaks) and was the 5-to-2 second choice in the Kentucky Oaks to Rachel Alexandra before scratching with a foot injury a couple hours before the race. Not only was she a very talented racehorse, but she was a very sweet filly to be around and was always a barn favorite regardless of her racing résumé. She has gone on to be a wonderful broodmare as well. Her first foal by Street Cry won the Breeders' Cup Juvenile last year (New Year's Day), and her second foal by Distorted Humor is already a 2-year-old winner in Europe. Her third foal is a Tapit colt that was the co-sales topper at Keeneland this September.
My personal best moment in the sport of Thoroughbred racing: I've been fortunate to have a lot of great moments at the track so far, but I would say winning the Tampa Bay Derby this year with Ring Weekend might be number one. We didn't make it to the Kentucky Derby with him due to a virus he caught the week before the race (nobody ever said horse racing was easy!), but to win a race like that, which qualified us for the Kentucky Derby, was very, very special.
My favorite trainer: I can't pick between Tom Albertrani, Craig Dollase, Graham Motion, Dale Romans and Dallas Stewart - all trainers who train my horses. They are all great people and great horsemen and it’s been a pleasure to get to know them over the past 10 years.
My heroes: Outside of racing, my parents and older brother. In racing, I really look up to Terry Finley - he is a West Point graduate and Army Ranger who started West Point Thoroughbreds with his wife over 20 years ago and has built it into one of the leading ownership groups in the country.
Person in Thoroughbred racing I’d like to have dinner with: I've had dinner with him a few times before but nobody tells a story like Dale Romans!
My philosophy on life: Enjoy the ride, work hard, love your friends and family and try to treat people you encounter in life with respect and kindness.
Favorite animal other than a horse: My wife and I have a dog, Holly, we adopted from an animal shelter four years ago.
Favorite non-Thoroughbred racing sports event I have attended: The New York Yankees winning the World Series in 1996. More recently, the New York Rangers beating the Montreal Canadiens at home to get to their first Stanley Cup in 20 years was pretty amazing!
Favorite food: Fresh fish
Favorite vacation spot: Hawaii
Favorite city: New York
Favorite TV show: All-time favorite, probably “Seinfeld”. More recently I'm completely addicted to “Game of Thrones”.
Favorite hotel: Ritz Carlton Kapalua. My wife and I spent our honeymoon there in 2008 and have been back every year since.
Websites I visit daily: Besides ABR, I go to bloodhorse.com, brooklynbackstretch.com and thisishorseracing.com for my horse racing fix. I also really like businessinsider.com for finance/tech news and deadspin.com for sports.
Pet peeve: Misusing their/there/they’re and your/you’re.
Favorite movie about horse racing: “Seabiscuit”
Which actor would play me in a movie: I've heard over the years I have a passing resemblance to Ben Affleck, but I don't see it. I'm thinking cartoon might be the safest bet.
Alma Mater: River Dell High School/Johns Hopkins University
Favorite radio shows/channels: HRRN and Howard Stern
Favorite memento: Trophy from my first graded stakes win
Favorite dessert: I only have it on Thanksgiving but I love pumpkin pie with vanilla ice cream.
Favorite drink: Jack and Coke
Favorite scent: Any summer morning in Saratoga!
What I like about my job: I like that it’s performance based and there is very little bureaucracy. I also really like the people I work with.
Favorite Tech gadget: iPhone
Twitter handle: @rmasiello
No. 1 Bucket-List item: Haven't won a Grade 1 race yet, so that would have to be it for now.