Penney Goes From Last to First

Shirl Penney wasn't supposed to be here. Standing in the Saratoga paddock, watching his Hall of Fame trainer saddle the favorite in the featured race of the day, preparing to be interviewed on live television. He makes sure, as he always does, to soak all of this in.

While only 39 years old, Penney tells stories the way an old war veteran would, which is understandable considering where he's been and what he's experienced. He has essentially lived two dichotomous, massively eventful lives in those 39 years, overcoming extreme poverty and immense odds as a child to establish himself in adulthood as a power player on Wall Street and a thriving presence in the Thoroughbred industry.

Penney is from the small fishing village of Eastport, Maine, population 1,400. Eastport is part of Washington County, among the poorest counties in the United States. He was born to a teenage mother who was going to put him up for adoption until an extended family member stepped in.

“My mother was 15 years old when I was born,” Penney explains. “I'm from the sticks of Maine. Eastport had a 50% unemployment rate. Five-zero. Back then, education was not a priority sometimes and a lot of kids didn't graduate high school, including my mother. She ended up getting pregnant early on, and was going to give me up for adoption, but my step-grandfather decided that he would take me in. He was divorced from my biological grandmother and was 60 years old at the time.”

Penney lived in a 350 square-foot home with his step-grandfather until he was 10 years old, when the house collapsed around them and was condemned. The two of them were homeless for three years, staying at times with various neighbors while the local carpentry school rebuilt their house.

“That was my youth,” Penney says. “I knew I wanted–and my granddad wanted me–to get a job someday where I worked with my mind and not my hands. My granddad only had a fourth-grade education himself and he really had a tough life, a lot of manual labor and he was handicapped.”

Penney became the first person in his family to go to college when he enrolled at Bates College in Lewiston, Maine. He studied economics and got hired at Smith-Barney when he was 21. Working his way up the corporate ladder for the next 10 years, Penney went out on his own in 2008 and founded Dynasty Financial Partners, a successful private wealth management firm that has allowed him to dive head-first into one of his lifelong passions, Thoroughbred racing.

“When I was at Bates,” Penney recalls, “I captained the baseball team and we always had an affinity for going to the horse track or the OTB. I always thought someday, if I could afford it, I would own a Thoroughbred racehorse.”

Initially dipping their toes in the water with syndicate involvement, Penney and his wife, Mary Ann, began Team Penney Racing in 2004. Mary Ann, also from humble roots as the daughter of a West Virginia coal miner, runs the day-to-day operations of the stable and names most of its horses. A proud alum of West Virginia University, she designed the Team Penney silks in the Mountaineers' navy-and-gold colors.

The Penneys' first horse was a filly by American Chance named American Dream'a, a play on Shirl's Maine roots and life story. She raced on opening day of the 2007 Saratoga meet in Team Penney's first start at the Spa and dead-heated for the win in the day's final race. The following year, the stable sent out Sweet Vendetta (Stephen Got Even) to an upset victory in the GII Black-Eyed Susan S. on a sloppy Friday at Pimlico.

The current stable star is Flipcup (Milwaukee Brew), a multiple graded stakes-winning mare who finished fourth in last Monday's Saratoga Dew S. The 5-year-old will run back in Friday's Yaddo S. on the Saratoga lawn, attempting to become just the ninth horse in American racing history to win a stakes race over dirt, synthetic and turf.

“We've had some great horses over the years,” Penney says. “We have a handful of mares, we breed, we also buy. At the yearling auction at Saratoga, I just bought a Giant's Causeway New York-bred filly that I really like. Hip #52. We have 12-15 horses, with Bill Mott, George Weaver, Brian Lynch and some at Finger Lakes with Chris Englehart. Jim Crupi at New Castle develops our babies for us. Both Sweet Vendetta and Flipcup were born at Waldorf Farm, where Dr. Jerry Bilinski does a nice job with the babies and mares. We will expand over time. Probably for us, the right size is 25-30 horses.”

Living and working in Manhattan, Penney is passionate about his job and puts in 16-17 hour days at Dynasty. Away from work, however, he and his family have centered their lives around horse racing. Shirl and Mary Ann's two daughters, eight and 10 years old, both ride, and the whole clan spends much of every summer at Saratoga.

“It's heaven on earth for me,” Penney says. “I feel the weight of a high-stress job with a lot of responsibility and it's a really nice escape from Wall Street. My friends and I joke that the night before opening day, at this stage of our lives, is like Christmas Eve. Ever since our kids have been born, we've never missed an opening day and we always yell, as a family, 'And they're off at Saratoga!' It's a great family tradition. My girls love it.”

Coming from the restrictions and despair of abject poverty to the kind of success and freedom that Penney now enjoys is a whirlwind that few could even imagine. In that Saratoga paddock scene, from where he's been to where he is, he must feel the need to pinch himself.

“I do, in all walks of life to be honest,” Penney admits. “I've lived a blessed life since I started in my industry. I get to do pretty much anything I want. All the sporting events, we eat at the best restaurants. My life now is pretty good, coming from being homeless. The two things that you know when you're really poor, if you ever go to bed really cold or really hungry, those things suck. Eating fish that I would have to go catch for breakfast for a long period of time was not a lot of fun. The odds of me being where I am today are more than a million to one. I've already won before the gates even open.”