Jack Diamond, known as Legs and sometimes as Gentleman Jack, took so many bullets and lived that the press and police called him the clay pigeon of the underworld. Born in Philadelphia in 1897 to Irish immigrants, he lost his mother as a teenager, moved to Brooklyn, and joined a Manhattan street gang called the Hudson Dusters. After deserting the Army and serving two years at Leavenworth, he came out in 1921 and went to work as muscle and then bodyguard for Arnold Rothstein. Prohibition let him build his own bootlegging operation, and a taste for Broadway nightlife put him on a collision course with Dutch Schultz.

This episode follows the unglamorous reality behind the legend: a drunken double killing at his Hotsy Totsy Club in July of 1929, witnesses who vanished, and a string of ambushes he survived on luck alone. It tracks his failed flight to Europe, where one country after another threw him out, and his slide into torturing a truck driver over a stash of hard cider. The end came in an Albany rooming house in December of 1931, hours after a jury acquitted him, and the strongest theory blames the local political machine that wanted no competition.

• Diamond had ships dump partly filled barrels of liquor offshore so the tides carried them to Long Island beaches, then paid local children a nickel a barrel to drag them out of the surf.
• In 1927 he was shot twice, once just below the heart, while guarding Little Augie Orgen on the Lower East Side. He survived and refused to name the shooters.
• In October 1930 two gunmen shot him five times at the Hotel Monticello. He walked into the hallway in his pajamas and drank two shots of whiskey.
• Sailing on the Belgenland as John Nolan in August of 1930, he was refused entry by England, seized in Belgium, arrested in Germany, and shipped back to Philadelphia on a freighter.
• On Dove Street in Albany one gunman held him down while another fired three times into the back of his head. No underworld figures attended his burial in Queens, and his widow was shot dead in Brooklyn in 1933.