During America’s massive middle-class expansion in the years following the Second World War, the city of Richmond briefly led the nation with the fastest-growing industrial economy in the country. Centrally located along the Atlantic coast, businesses found Richmond attractive because it was the northernmost city among the bloc of anti-union, right-to-work states of the South.
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Richmond’s Tobacco Row, a stretch of six cigarette factories along the James River riverfront in Shockoe Bottom. Harry Donovan commissioned men working at the factories to sell pick-three numbers bets among coworkers in the lunchrooms and locker rooms. (SOURCE: 1948, Valentine Museum)
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Between 1940 and 1950, the city’s population surged nearly 20 percent. During this period of postwar prosperity, Richmond grew into a sizeable blue-collar town. About 3,800 employees manufactured rayon fiber and cellophane products at south Richmond's sprawling DuPont facility. Philip Morris, Lucky Strike and other tobacco companies employed many thousands more, rolling out millions of cigarettes each year at enormous riverfront factory warehouses in Shockoe Bottom still known locally as “Tobacco Row.” Reynolds Metals would soon employ 3,100 people at its aluminum and foil packaging operations.
Richmond’s tremendous growth during the 1940s also presented opportunities for numbers kingpin Harry Donovan. During this period, Donovan was paying commissions to more than 800 people who wrote numbers for him across the city every day. Donovan commissioned men working inside the city’s largest factories to take numbers bets among their coworkers as they circulated daily through vast lunchrooms and locker rooms. And many employers were said to tolerate the illegal gambling activity: the winning numbers often were posted on employee bulletin boards at several Richmond factories.
Donovan was strategic in other ways, too. To protect his profitable Richmond territory, he expanded his daily numbers racket north to Fredericksburg, west into Charlottesville and south to Petersburg -- and dialed-up the daily payouts in those cities to the point of unprofitability -- to discourage out-of-town gambling syndicates from making a move against his Richmond operations.
“We conducted our business in a businesslike way and behaved like gentlemen,” according to Donovan’s nephew, Charles E. Jenkins, who managed Donovan’s office during this period. Jenkins said the average bet was about five-cents and the typical payout was 500-to-1. Payouts in Fredericksburg and Charlottesville were increased to 600-to-1, which “was a losing proposition” according to Jenkins, but it made certain strategic sense.
“Anytime that you pick up a Washington paper, it would be a killing or shooting or somebody hurt in Washington over numbers, and it never did happen in Richmond,” Jenkins would later testify. “That is why it was shut-off at Fredericksburg: we knew if they got to Fredericksburg, it wouldn’t be long before they would be in Richmond. And if they got to Fredericksburg, they were certainly going to bring an undesirable element into Fredericksburg and that would certainly come into Richmond,” Jenkins said.
Donovan's numbers racket was a big business, and the profits were accumulating quickly. During the 1940s, Donovan asked several close friends and family members to hide bricks of cash for him to guard against robbery, police raids or IRS seizures. After selling his Henrico County horse farm to make way for construction of the Reynolds Metals corporate campus, Donovan began looking for another property where he could invest his cash, further indulge his interest in racehorses and continue building the façade of respectability he appeared to crave.
In the late ‘40s, the gambling kingpin purchased Thorncliff, a baronial estate in Goochland County built on a tall bluff overlooking the James River about 25 miles west of the city. “Thorncliff once contained all of the accouterments of a Gilded Age estate: a large mansion, numerous outbuildings, horse barns, and it even had its own private train depot,” local historian James Richmond wrote in a 2016 article for the Goochland Historical Society titled “Racehorses & Racketeers: The Story of Thorncliff.”
Thorncliff, the Goochland County estate built by VMI graduate and onetime Confederate Gen. Joseph Anderson, photographed in circa 1900. In the foreground is Thorncliff’s miniature stone railroad depot. The grand house on the bluff burned to the ground around 1900. Richmond numbers racketeer Harry Donovan owned Thorncliff in the 1940s and 50s. (Source: VMI Archives Photographs Collection)
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The estate was built as a country home in the decades following the Civil War by Gen. Joseph Reid Anderson, a VMI graduate and onetime Confederate officer whose family owned Tredegar Iron Works in Richmond. Thorncliff’s main house was destroyed by fire in the early twentieth century, but the estate’s showstopping feature remained its huge, cupola-capped, two-story horse barn. Framed around a central courtyard, the massive barn featured a third basement level built into a gently sloping hillside containing rows of horse stalls.
“Maybe buying Thorncliff was Harry Donovan’s step-up from the image of a scrappy little bootlegger,” James Richmond told me during a May 2019 interview. “He gets progressively nicer houses in the city, and then he gets a big, landed estate in Goochland. What would fit even better? Thoroughbred horses.”
(©1994, Goochland Yesterday and Today: A Pictorial History,
by Cece Bullard)
Donovan quickly established a substantial horse breeding and training operation at Thorncliff. He hired dozens of professionals to operate the farm, bringing some experienced trainers from Europe. Donovan spent more than $60,000 [equal to $650,000 in today's dollars] on fast, expensive and well-bred horses, and Donovan himself became a minor figure on the East Coast racing circuit.
“It was a lot of work. I know one of the women that I talked to came from England to work on his horse farm,” Richmond told me. “It obviously was a much bigger operation than we think if he’s pulling people in from another country to come over and take care of his horses. There seems to be a lot going on there.”
One Goochland resident told the historian that Donovan was seen as a generous neighbor, recalling how he helped her family when she was a child. “If they needed anything, suddenly they got it. They needed a washing machine, and suddenly a washing machine was delivered to their back door,” Richmond told me. “She called him ‘Uncle Harry.’ He seems to have been well-loved by the family.”
In the mid-1950s, the entrepreneurial Donovan identified a promotional opportunity to perhaps offset some of the tremendous expense of maintaining an operation as substantial as Thorncliff. He constructed a half-mile oval track and joined a regional network of pop-up tracks hosting community races. These races featured mostly B-grade horses -- those racehorses unable to rise, or beginning to falter, within their class. It would come to be known as The Hambone Circuit.
In this modern-day satellite image, you can still clearly see the half-mile oval track Harry Donovan constructed across the road from his Thorncliff farm. Beginning in the mid ‘50s, he hosted an annual community race day at Thorncliff each spring. (SOURCE: Google Earth)
Each spring, Donovan’s Thorncliff Races would attract hundreds of local families and spectators for a daylong festival of seven or eight races which ostensibly raised money for charity. For instance, the first year’s race reportedly was staged to try to raise $6,000 to purchase lights for the Goochland High School football field. He enlisted the local American Legion post to serve as the named sponsor.
The annual Thorncliff Races grew to be a substantial enough event to be covered by local newspapers. One sports reporter for the Richmond Times-Dispatch described the first Thorncliff Races as “a sun-kissed turnout of close to 1,000 on the picturesque rolling estate of Mr. and Mrs. H.L. Donovan.”
“The people here in Goochland certainly enjoyed the races. Everybody. You took your family to the races. Sure, there was some betting going on, but it’s a horse race: there’s always betting in a horse race. It’s no secret,” historian James Richmond said. “It’s absolutely brilliant. He’s got the American Legion as a co-host of this event. He’s got the fire department doing concessions. What better way to make it look prim, proper and genteel than to have these well-known organizations in the community come out and say, ‘This is perfectly fine – come see us.’”
Donovan’s Thorncliff Races occasionally attracted unwelcome press attention, too. Just days after the first event, the Goochland Gazette featured a front-page article under the headline “County Ministers Deplore Gambling, Drinking at Thorncliff Races.” The local ministerial association unanimously adopted a resolution expressing “profound concern over the widely reported public gambling” during the Thorncliff Races. “We respectfully suggest to the sponsoring group that they make every effort to avoid a repetition of this flagrant violation of the laws of our State and of Christian ethics,” read the resolution.
Donovan would stage the races, presumably with more discreet gambling and drinking, each spring until 1960, when he quickly sold most of his major assets before reporting to prison following his conviction on charges related to his Richmond numbers syndicate. The sale price reportedly was $160,000 -- equal to about $1.5 million in today's dollars. “Out of the sale of that farm, he did not make one five-cent piece,” his attorney would later say.
And there’s an interesting circularity to this story: Donovan purchased Thorncliff in the late 1940s with the proceeds from the sale of his Henrico County horse farm to make way for construction of the Reynolds Metals headquarters building. When he needed to unload Thorncliff in a hurry before reporting to prison in 1960, he once again turned to the Reynolds family: Donovan sold Thorncliff to William and Mary Reynolds, the son and daughter-in-law of the Reynolds Metals founder, Richard Reynolds.
When I spoke with James Richmond, the local historian, in 2019, he said he still occasionally encounters Goochland residents who remember Harry Donovan, though they tend to speak of him “in hushed voices,” perhaps due to his later notoriety. "It’s hard to pull them out to talk about Harry Donovan. It seems to be something they’d rather keep under the rug. Now, whether they are embarrassed about it or whether they’re a little protective of him, it’s hard to say...”
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