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About KINGPIN

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Harry Donovan (dark suit) is led off to federal prison in 1960 following his conviction on tax charges for operating a massive illegal lottery in central Virginia. SOURCE: Richmond Times-Dispatch

In the decades between The Roaring Twenties and JFK's New Frontier, Harry L. Donovan, son of an Irish immigrant, grew to be a man of wealth and influence in Richmond, Virginia. 

 

Donovan ran a successful jukebox business and employed hundreds of people. He lived in a grand house in Richmond's most desirable neighborhood. He also purchased a weekend estate along the James River where he trained thoroughbred racehorses.

 

Donovan was on a first-name basis with many of the area's business leaders. His family's summer travels were mentioned in the society columns of the Richmond newspaper.

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Yet for more than 25 years, the scrappy ex-bootlegger also operated one of the largest illegal numbers rackets in Virginia. Donovan paid as many as 800 street-level runners to solicit up to 50,000 illegal lottery bets every day.

 

The federal government took aim at his multi-million dollar criminal enterprise in 1936 and again in 1955, but Donovan always managed to slip away. In 1960, the IRS sent an undercover team to Richmond and finally took him down using the same methods used to send Al Capone and other gangsters to prison. 

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KINGPIN is author Kevin Hall's look at the colorful, largely untold story of bootlegging and illegal gambling in mid-century Virginia.

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