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  • Writer's pictureKevin Hall

Meet Leo Seay, a top Donovan lieutenant

Updated: Sep 15, 2021

Prohibition is when we first meet Leo Seay of Richmond, who many years later would serve as a top lieutenant in Harry Donovan’s numbers racket. An unkind reporter would later describe Seay as "a ferret-faced ex-bootlegger addicted to slouch hats and sunglasses."


Seay was born in Italy in 1902, and his family emigrated to the U.S. and settled in the Richmond area around 1915. Even as a relatively young man, Seay methodically began to build an impressive criminal record.


At the age of 17, Seay was arrested with two others in Maryland after stealing two Cadillac automobiles in Richmond and driving them north to Baltimore to sell. Baltimore police followed the Richmond men for hours before growing weary, finally confronting the car thieves around 3:00 AM. The following year, perhaps as some sort of cheeky joke, Seay would list his occupation on U.S. Census forms as "chauffeur."


In 1927, 25-year-old Seay was arrested by revenue agents while driving a car loaded with sugar, malt, and kegs toward a Charles City County ferry crossing. The Daily Press newspaper reported that the vehicle also contained “217 gallons of fluid madness,” most of which was poured into the nearby James River.


In 1929, Seay was charged in the kidnapping and beating of a Richmond man who allegedly had told authorities about the location of an illegal still which had been successfully raided and shutdown the previous week.

In 1931, at the age of 29, Seay appeared in court on charges of illegally selling a dozen bottles of beer out of his apartment on North Monroe Street in downtown Richmond. He was acquitted after it was discovered someone had broken-in to the court’s evidence room in the basement of City Hall the night before Seay's trial – brazenly gaining access after sawing through the barred windows at street level outside -- and swapped the incriminating evidence with identical bottles of water. In court the next day, the police chief would sheepishly tell the judge that yes, he certainly would give due consideration to His Honor’s helpful suggestion that steps might be taken to better secure the evidence room.


Once Prohibition ended in 1934, organized crime and street-level crooks turned to illegal gambling to replace their lost income. In 1939, Leo Seay was picked-up at a suspected gambling headquarters on Broad Street where police hoped to catch several "higher-ups," including Harry Donovan. Instead, all they seized were numbers slips, several adding machines -- and Seay. He was fined $75 and given a three-month suspended jail sentence.


During the 1940s, Seay worked as the manager at The Turf Club, a private club near Belvidere and Broad streets which made the news several times for liquor and gambling violations. In 1945, Seay successfully appealed a conviction for illegally serving a mixed drink to an undercover policeman.


The following year, Seay and the operators of The Turf Club were convicted on misdemeanor charges of operating “a common nuisance,” a catch-all liquor violation which the Virginia Alcoholic Beverage Control Act defines like this: “All houses, boathouses, buildings, club or fraternity or lodge rooms, boats, cars and places of every description where alcoholic beverages are manufactured, stored, sold, dispensed, given away or used contrary to law, by any scheme or device whatever.”


In 1947, police raided a gambling operation in an upstairs room at The Turf Club. According to the Richmond Times-Dispatch, the room was outfitted “in classic horse racing bookie style,” with several chalkboards for posting odds and results and a loudspeaker used to broadcast closed-circuit race results. Police also seized two pinball machines that illegally paid-out cash prizes.


Seay himself was not arrested during that 1947 raid, but the same cannot be said for the Turf Club employee at the reception desk who unsuccessfully lunged for a secret buzzer to warn those gathered upstairs, or for the 15 customers captured when the cops burst through the steel-reinforced door at the top of the stairs.


In the late 1940s, Leo Seay went to work as a “pickup man” for numbers kingpin Harry Donovan. By the time of his January 20, 1960 arrest, he would have been 58 years old. He was arrested by IRS agents after weeks of surveillance as he sat in his blue Mercury parked at one of his usual pickup locations.


IRS agents found several brown paper bags of betting slips on the floorboard on the passenger side of Seay's car. While the agents were searching the vehicle, at least a half-dozen other cars approached, made awkward U-turns and quickly sped off. Agents later testified they saw bags of play slips being tossed from the windows.


According to trial transcripts, Seay initially wasn’t very communicative: “You’ve got me. You’ve got the tickets. What more do you want?” he allegedly told the agents. He was more forthcoming at booking, when he truthfully listed his occupation as “gambler.” Seay ultimately would be convicted on state gambling charges, fined $2,000 and sentenced to three years in prison, with two years suspended, for his role in helping to run Donovan's numbers racket in Richmond.


Little information can be found about Leo Seay’s life after prison. It appears he remained in the Richmond area, and he died in a local hospital in the fall of 1981 at the age of 79. The death certificate lists his last known occupation as a truck driver for a local gravel company.


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