When one thinks of the gambling scene in the 1920s, 30s, and 40s, the likes of Al Capone, Frank Costello, and Bugsy Siegel immediately spring to mind. However, the District had its own gambling godfather — Jimmy Lafontaine. He couldn’t have been further from the American gangster archetype. Though his extralegal line of work inevitably brought him unwelcome brushes with mobsters and the law, his story is not one of bootlegged booze or mysterious murders. Rather, he’s most often remembered for his charity and reputation as Washington’s “gentleman gambler.”
On Memorial Day 1904, a group of civilians led by Alexandria County Attorney General Crandal Mackey boarded a southbound train from their meeting point in Washington to present day Arlington. As they rode over the old Long Bridge, Mackey distributed axes, guns, and hammers to the men who, only moments earlier, had been sworn in as official deputies. For decades, seedy settlements rife with betting houses, bars, and boudoirs prospered in the shadow of the nation’s capital. Gamblers had long sought protection by backing the powers that be in the dominant Democratic Party but Mackey and his supporters were a part of a new movement that claimed to oppose corruption. Mackey’s posse disembarked at the unimaginatively named “South End of Long Bridge Station” and began what would be the first of many raids. Haphazard in their approach, the gang swarmed well-known gambling houses and left smashed-up, burned-out shells in their wake.
The St. Asaph racetrack in Alexandria was a hotbed of gambling at the turn of the century, and local prosecutor Crandal Mackey made it his personal mission to shut the track down. But that was easier said than done as the track's owners concocted elaborate schemes to outwit authorities and circumvent Virginia's anti-gambling statutes.