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Since most of the stories of mayhem came from the man himself, it is difficult to know how much to believe. The 1920s gangster costume can be summed up as men in dark suit jackets (often striped, never black) with matching vests and pants, a white or black band fedora hat, a contrasting tie, and a fat cigar in his mouth. The same year he was tried, though later cleared, for attacking his third wife Jennifer Pinto, a rap artist named JennyBean, over an alleged lesbian affair. Scottish mobster involved in extortion, narcotics and drug trafficking in Glasgow from the 1970s until his death in 2007.
Referred to as the "King of Racecourse Gangs" and leader of the Sabini's, Ottavio Handley, more commonly known as Charles Sabini was a turn of the century era mobster who controlled many of the racecourse betting rackets in London until his imprisonment in 1940. He was a patron of Autistic Inclusive Meets (AIM) and of Misunderstood, a children’s ADHD charity in Rochester, Kent, and was reported to have done work with the Prince’s Trust. In January 2009 he was given an 18-month conditional discharge after admitting possessing live ammunition. Another option is the black homburg, also worn in the 1940s and 1950s by The Godfather, a mafia legend. Gangster / mafia outfit – Black homburg hat, dark grey striped suit, two tone shoes, leather gloves and a walking cane (or is it a weapon?Capone owned several Panama hats and even imported a hat maker from Ecuador just to make them for him.
The index to his memoirs was littered with such names as Caesar the Geezer, Fred the Head, Bulldog Dean, Eight Ball Pete, Jimmy Five Bellies, Jack “The Hat” McVitie and John “Mad Dog” Mangan; there were 23 entries under “B” for “Big”. A childhood friend of the Kray Twins, he was used as a go-between by the Richardson's until his murder by Ronnie Kray at The Blind Beggar pub in 1966. Cigar – Gangsters always have a cigar in hand and a shot of “bootleg” whiskey in a flask by their side.In addition he wrote columns for Front, a rival to the lads’ mag Loaded, recorded a version of I Fought the Law with the Scottish punk band Mute, addressed the Oxford Union and cultivated a sideline as “gangster chic” style guru.
Involved in the Brink's-Mat robbery in 1983 and subsequently stabbed police officer John Fordham to death.His first two marriages, to Susan Ray and Annette Barn, were dissolved and he was separated from his third wife, Jennifer Pinto, a rap artist known as JennyBean. Brown stripes, plaid, or tweed may have been worn for casual day meetings and by lower ranking bootleggers. Lured to an underworld party, he was murdered by Reggie Kray following the failed gangland hit on suspected informant Leslie Payne.
Like Capone, Siegel was recognized as a celebrity gangster who was greatly feared among rivals and accomplices.In summer, the hat of choice for wealthy men, including gangsters like Al Capone, was the straw Optimo Panama.