UConn Magazine: Billion Dollar Bailey

Running gave Trisha Bailey her start in life and continues to be an inspiration

Bailey at her 59-stall horse ranch in August.

Bailey at her 59-stall horse ranch in August. (Peter Morenus/UConn Photo)

Air you can wear. That’s how the meteorologist describes the weather in Orlando this August weekend, and at 10 a.m. the track already shimmers with heat. But when she strides onto the red rubber, she is fresh as a CEO in an air-conditioned boardroom about to announce a better-than-expected earnings report. She’s in high heels and it’s 96 degrees Fahrenheit with 100% humidity, and she looks like she’s a whistle away from taking off, a streak of black on red running an 800 like it’s 1999.

“I love the track. Stepping on it gives you a high every time, it’s like ahhhh,” Trisha Bailey ’99 (CLAS) says. But instead of sprinting down the track, she stands patiently as her friend and former teammate Kathy (Holloman) Jackson ’99 (BUS), ’02 MA fixes a stray lock of hair, and her publicist uses a little saliva and palm grease to rub dust off her blouse. “You’re such a mom,” Bailey compliments the publicist. Then she shows off her nails, bejeweled to spell “Unbroken.” The name of her book being released this weekend is also the perfect word to describe the indefatigable founder of a business empire that stretches from Connecticut to Jamaica. Because broken she could have been.

But in this moment she is the perfect boss lady, the proud Jamaican-born woman who calls all the shots, who runs 16 businesses and a philanthropic organization while raising five children, a mover and a shaker.

Her ability to move — fast — is what first distinguished Bailey. She had early success on the track her sophomore year at Hartford’s Weaver High School. And even after her track coach left without a replacement, Bailey continued training, and winning. That track success brought her to UConn, but there was a catch. Her SAT scores were not good enough for her to compete according to NCAA rules at the time. Amazingly, the University took a chance and gave her a scholarship anyway, in expectation that she would get the necessary grades and start winning as soon as she got back on the track.

Freshman year found her at UConn, but still training for the track on her own — and having to succeed at college level work. Gradually Bailey developed a study strategy. Some of the football players had asked to borrow her notes, but she said she would teach them the material instead. When she found she learned better herself that way, she made tutoring the players a regular part of her study schedule, and began getting the grades she needed to compete.

Read on for more.