September 1, 2022 — Famed professional gambler and convicted underworld bookie Alan (Dinky) Denkenson died of cancer this week He was 69 years old.
The Queens, New York native had become a titan in the Las Vegas gambling space over the past three decades, known for his handicapping skills, appearances in the World Series of Poker and his signature fluffy mane of dark hair. Since the advent of social media, Denkenson was a well-known presence on “tout” shows and sports-gambling talk outlets in the media
Dinky Denkenson was indicted on federal bookmaking charges in 1991 in a case out of Detroit targeting the notorious Giacalone mafia crew. According to the indictment, Denkenson was the Giacalones layoff man in New York City and the groups liaison to the Gambino crime family, the organization Denkenson’s book was protected by. He pleaded guilty and did two years in prison. After his release in 1993, he relocated to Las Vegas.
Denkenson was such a character and his life such a whirlwind, the 2012 Hollywood film Lay The Favorite is a dramatization of him based on a memoir penned by his one-time personal assistant. In the movie, Bruce Willis plays a character named “Dink” Heimowitz.
The No. 1 and No. 2 defendants in Denkenson’s ’91 felony case were Vito (Billy Jack) Giacalone and his son, Jack (Jackie the Kid) Giacalone. Billy Giacalone (d. 2012) was a longtime power in Detroit’s Tocco-Zerilli crime family and was one of the top suspects in the 1975 disappearance and murder of Teamsters boss Jimmy Hoffa. Jackie Giacalone, 72, is allegedly the don of the Detroit mafia today, per sources.
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