February 15, 2025
Sports

Penney strikes gold with horse Shead grad also shines at Citigroup

Whether if it’s by land or sea, there’s plenty of distance between a condemned saltbox on Franklin Street in Eastport and a Hudson River shorefront mansion in Weehawken, N.J.

Shirl Penney has proven you can get there from here, however, and you can do it much faster on horseback.

The 31-year-old Shead High School alumnus (Class of 1995) was already the embodiment of the American dream, going from poverty and big dreams as a child to undisputed success and big bucks as an adult, but his latest accomplishment is well beyond even his imagination.

The former blueberry raker and salmon farm worker has now added successful thoroughbred horse owner/breeder to his “real job” title as director of business development for wealth management at Citigroup/Smith Barney.

Until Friday afternoon, you could also call Penney the owner of Sweet Vendetta – the winner of the prestigious Black-Eyed Susan Stakes, the second leg of the “Triple Crown” series for fillies (females).

“Yeah, it was a very tough decision, but when you have a chance to guarantee a college education for your children and your grandchildren, you have to take it,” said Penney, referring to his sale of the first New York-bred thoroughbred to win the Black-Eyed Susan in 21 years.

Penney couldn’t reveal the final sale price, but a bidding war for the filly, who finished the 1 1/16-mile race in 1 minute, 49.60 seconds on a muddy track May 16, reportedly drove the figure slightly over the $1 million mark. Adding that to Sweet Vendetta’s lifetime purse winnings of $206,596, it’s quite a return on a $30,000 investment a little more than a year ago.

“I was a big fan of her older sister, Half Heaven, which [trainer] Gary Contessa trained in New York,” said Penney, who currently owns 12 thoroughbreds. “I was looking at a sales catalog with the pedigree sheet after my daughter [named Townsend after her great-grandfather] went to bed.

“[Sweet Vendetta] had hit her foot on a stall and had a scar on her foot and they entered her as kind of a brood mare because of the scar. I thought maybe it could run and asked Gary about it.”

Contessa and Penney have a unique relationship, and it’s that kind of input that makes it successful as well.

“I’m certain Gary will say I have too much input and would like me to be a little more laid-back,” the former four-sport athlete at Shead said with a chuckle.

“I would say it’s kind of like George Steinbrenner and Billy Martin,” Contessa joked. “We have great communication.

“Unlike Steinbrenner and Martin, we’re very good friends, and it shows in the way we deal with each other.”

After Contessa did some homework and research on Sweet Vendetta, the Calais-born Penney and Long Island-bred Contessa went to Kentucky to buy at auction the daughter of standout racehorse Stephen Got Even and dam Sand Pirate.

“David Cassidy was going through a bad breakup with a business partner, so they were liquidating their horses,” said Contessa, The New York Thoroughbred Breeders’ three-time trainer of the year who has worked with Penney the last three of his 23 years in the business. “We were willing to bid up around $100,000.”

Any doubts Penney and Contessa had about the horse were quickly dispelled. After the gavel came down for the final time, another buyer offered $50,000 for Sweet Vendetta. After that offer was rejected, actor/singer Cassidy asked to buy a 25-percent share of the horse because he believed in her that strongly.

Penney, his wife Mary Ann, Cassidy and Contessa were joined by Lewiston native Dave Moore, who runs the mailroom at Bates College. Moore and Penney became friends while Penney was studying business and finance, playing baseball and doing work-study jobs at the Lewiston college. The two found they had a mutual interest in horse racing.

“I used to go to Scarborough Downs a lot with my teammates at Bates and go to the OTB at Lewiston,” said Penney, who was Bobcats’ team captain. “I always said if I ever could afford it, I’d like to own a horse. [Moore has] always been interested in getting in on ownership of a horse, so I called him and offered him a chance to buy 10 percent of Sweet Vendetta.”

Penney’s glad he did. One of the highlights of the entire race experience was watching Moore as the race ended.

“Seeing Dave’s face and seeing my wife cry with my daughter there as she crossed the finish line was the best,” Penney recalled. “Probably one of the most enjoyable moments was in the paddock before we took Sweet Vendetta out for the cameras and everything… I got a little emotional because I was thinking about my life’s journey up to that point. It really all came back to me.”

Investing in a dream

While his friends were reading Sports Illustrated, Penney was scrounging around for enough money to get a subscription to Money magazine.

“We didn’t have a lot of money growing up. My granddad raised me and we used food stamps and Social Security, and even had our house condemned when we were living in it,” said Penney. “I discovered a passion for finance and Wall Street in high school. I was always fascinated by the market in general. Everybody in Eastport thought I was crazy. I talked to a lot of tourists about it to find out more and more about it. I would ask for them to bring Wall Street Journals because you didn’t see them around.”

Penney’s mother, who was 16 when she gave birth to him, gave parental control to her stepfather, Clarence Townsend, rather than put Penney up for adoption, Penney said. The two were nearly inseparable until Townsend died in 1999 at the age of 80, one day before Penney’s Bates graduation ceremony.

“Me going to college was a huge goal of his. No one in my family had gone to college before, so that provided a lot of motivation,” said Penney, who did any job he could fit into his schedule and combined that with money from loans and scholarships to fund his Bates education. “I owned a newspaper distribution business at Bates, which I bought really cheap and sold for a good profit. I also sold antiques on eBay. Whatever I could make money doing, I did.”

After graduation, he interviewed at several firms.

“I went to the Salvation Army in Lewiston, bought a suit for $13 and interviewed for a number of firms, including my favorite, Smith Barney, which hired me,” said Penney, who worked at the World Trade Center until 2001. He moved to San Francisco about eight months before the World Trade Center was destroyed in a terrorist attack. He went on to become the youngest director for Citigroup.

Things went full circle for Penney two years ago when he returned to Shead High to deliver the graduation commencement address and start the Clarence Townsend scholarship fund.

“I just want to make my granddad proud and happy,” he said. “As for me, I would say at this point I’ve definitely exceeded my own expectations.”

aneff@bangordailynews.net

990-8205


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