On February 14th, 1929, gangster “Scarface” Al Capone’s gunmen exacted revenge upon the rival North Side Gang in an execution-style shooting that would become known as the St. Valentine’s Day Massacre. For anyone who even knows the slightest bit about the organized crime killings of those years, the St. Valentine’s Day Massacre is probably the one you think of, the one memorialized by vivid photographs of murdered men slumped against a garage wall and collapsed in pooling blood.

Those images have contributed to Capone’s name being synonymous with the word “gangster.” Capone maintained some strong connections to racing, too. Of course, horse racing and organized crime pop up as linked in popular culture often: the horse head in The Godfather belongs to a racehorse, and it is hard to forget Tony Soprano’s affection for his racehorse, Pie Oh My, who suffered a similar, allusive fate.

Some sources say that even as a child, Capone was drawn to horses. His older brothers would take him on pony rides at a Staten Island stable. He allegedly owned part of Sportsman’s Park racetrack in Cicero, Illinois. But apparently he was no great bettor, a fact brought up in a colorful New York Times piece by Meyer Berger, who was covering Capone’s trial in 1931. Jurors “got a picture of Capone the ‘sucker,’ the naïve backer of races horses which never won,” Berger wrote. “The hundreds of thousands he made in his own gambling houses from the lesser sports of [New York] were dropped by the handful into the laps of other gamblers—in one pocket and out of the other. . .By this line of testimony the defense will seek to prove that the alleged great income of Capone, as brought out in the government evidence, dwindled almost as fast as it came in and that little remained for the government to tax. . .William Yario, a small, rotund man with mousy remnants of a hair crop, carried his black derby to the stand with him. He squinted at Al.” Yario testified that Capone would bet “Sometimes a t’ousand, sometimes t’ree t’ousand. If he was winners, he bet more.” Apparently, Capone was not “winners” often.

Several witnesses testified “that the Capone bets, running from $1,000 to $5,000 on a horse, had to be shifted at times to other men at the track, because they did not have enough to cover.” (Apparently, however, racetrack managers and others holding his notes knew better than to ask him to make good on his many IOUs.)

Dogwood Stable owner Cot Campbell tells a story about Ben and Jimmy Jones—legendary father-and-son trainers of Calumet Farm–and Capone. The Joneses were at Chicago’s Arlington Park when Capone told the trainers, “I wanna cash a few bets, so I might want to hook up with youse. You probably got a live horse or two left in the barn. Maybe we could have some fun together, and I’ll take care of you if we do.” As Campbell writes, “Jimmy and Ben deduced that if the ‘live horse’ did not generate fun, indeed they might be taken care of in another way.'” The Joneses accepted an invitation to dine with Capone, who reiterated that he would like to be cut in on the next sure thing the Joneses trained. Ben and Jimmy decided to enter their fast filly Missouri Waltz in a claiming race, reasoning that although she might get claimed, it would be worth it, because she’d win for Capone. She won, and the other horsemen, understanding the situation, didn’t claim her. Ben, Campbell reports, “called Jimmy over. ‘By God, I’ll tell you where we’re going from here. Soon as there’s an eastbound train, and it’d better be a night train, we’re taking the whole damned outfit to Latonia. I don’t want no more of this.'” The Joneses stayed away from Chicago until Capone was safely in prison. He left a name as an owner, though. In 1932, the New York Times reported that a horse named Charm, “a former Capone racer,” won a race in New Orleans.

Years after the St. Valentine’s Day massacre, ties between Capone and racing continued to surface, even in tangential ways. One of the guns purchased for Capone in 1929 was found in Miami when horse owner and trainer Jack Whyte grabbed it from the hands of a robber trying to hold him up. “Another pistol from the consignment was used, police said, in the New York slaying of Franklie Uale, gangster. The consignment was traced through the slaying to a Miamian, who, it was alleged, bought the gun for Capone, then wintering in Miami.”

From St. Valentine’s Day to racing, Scarface casts a long shadow.