Alumni Spotlight

Gilliard ’97, Colonial Downs VP of Legal Affairs, Helps Lead ‘Racing Revival’ in Virginia

Stephanie (Waters) Gilliard ’97

By Shannon Ballard Gorman
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Stephanie (Waters) Gilliard ’97 has used her lawyering skills to help bring thoroughbred horse racing back to the Commonwealth of Virginia and build an economy-boosting gaming industry.

In October 2018, Gilliard became the vice president of legal affairs and general counsel-Virginia for Colonial Downs Group, which operates Rosie’s Gaming Emporiums. After 12 years of being in-house counsel for health care companies and accumulating extensive corporate law experience, she was ready for her next challenge as a general counsel. When the opportunity came, despite knowing little about horse racing, she thought, “Why not! Take a little risk.”

The Colonial Downs Racetrack in New Kent, Va., had been dormant since 2013. Home to the Virginia Derby since 1997, it boasts the widest turf track in the U.S.—a track named after racing great Secretariat, who was a Virginia-bred Triple Crown champion.

“There are so many historical connections to horse racing in Virginia, and a lot of vendors and suppliers lost a significant portion of their income when the track closed,” Gilliard said. “Bringing it back meant a lot to the local economy and boosted the income of many New Kent county and neighboring county residents.”

Chicago-based Revolutionary Racing bought the defunct race track and, with other investors, formed the Colonial Downs Group, with the intent to revive thoroughbred horse racing in Virginia. But first, the existing regulation that permitted pari-mutuel wagering had to be implemented to address a new form of wagering technology.

Colonial Downs’ decision to resurrect live horse racing in Virginia was driven by economic development gains, specifically in agribusiness. However, they need an associated gaming operation to fund the purses for the thoroughbred races.

As gambling was not legal in Virginia when Revolutionary Racing purchased Colonial Downs, the company’s first challenge was to lobby the state legislature to pass a bill allowing pari-mutuel wagering with historical horse racing terminals, which have the look and feel of slot machines but players can turn off the auto-cap feature and use skill to handicap races before placing bets. The machines use historical data from thousands of horse races to determine which horses could win, place, or show.


“I’m still learning all the horse racing terminology. It’s been a big learning curve,” said Gilliard. “It makes me wish I’d gone to Saratoga more when I lived in Albany!”

Rosie’s Gaming Emporiums are inspired by Rosie the Riveter. “Our company is based in the Virginia Peninsula area, which is filled with military bases, personnel and veterans, and we want to honor those who have served in many ways,” Gilliard explained.

She also helped get the necessary special use permits to develop the gaming sites, and became totally entrenched in the planning commission process, zoning requirements, building permits, and a slew of contracts. The senior leadership team, dubbed “Rosie’s S.E.A.L.S,” would meet weekly to discuss progress on launching each facility. “The energy was palpable,” Gilliard said. “That has been my favorite part of the job so far—the excitement of creating something from scratch and seeing it come to life.”

This past year, they have held groundbreakings and grand openings at Rosie’s Gaming locations in Hampton, Richmond, and Vinton (east of Roanoke), as well as the horse racing track and gaming parlor in New Kent (just east of Richmond). Horses began arriving at the track in late July, and the meet began August 8. The opening day card featured 10 races, 107 horses, and $515,000 in purse money.

“We had a great revival,” Gilliard said. “We received so much positive feedback from patrons who are extremely happy with our return.” She added that they are most proud of the economic influx they have brought to racing industry vendors and workers—everyone from hay providers to track cooks.


Gilliard is also proud that Colonial Downs is committed to giving back to its team members and communities. They asked Gilliard to develop a corporate social responsibility policy, which she did, and it was approved and adopted at each location. The policy then led to the creation of a program called Rosie’s Gives Back; each property will donate $100,000 annually to the community in which it operates.

“We focus our giving on education, veteran programs, and local area needs,” Gilliard said. “The program is one of the most rewarding aspects of my role at Colonial Downs.”


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