This year’s honorees include a Midwest retailer and two multi-store independents, one in New York and the other in New England.
Possessions of Infamous American Gangsters Up for Auction
RR Auction’s “Gangsters, Outlaws and Lawmen” sale will include a promise ring Clyde gave to Bonnie and a pocket watch once owned by Al Capone.

Boston--Al Capone, Bonnie and Clyde, Whitey Bulger--you know their names, and soon you could own part of their history as well.
On June 24, Boston-based RR Auction will hold its “Gangsters, Outlaws and Lawmen” sale, featuring a number of items belonging to some America’s most infamous criminals.
One of the most notable items in the sale is a ring Clyde Barrow gave to Bonnie Parker.
Though the duo robbed a number of jewelry stores in their days, this ring is attributed solely to Barrow’s “craftsmanship,” the auction house said.
Just two months after meeting, he was arrested and spent the next two years in prison, where both he and his brother engaged in a number of crafts to pass the time, including jewelry-making, leathercraft and woodworking.
“He must have crafted this ring for her during that period as a sort of ‘promise’ ring. They were never officially engaged,” said Bobby Livingston, executive vice president at RR Auction.
The ring features a three-headed snake set with faux green and red gemstones. The auction house said it’s likely Barrow--whom historians now know was very artistic--made this ring with a base metal (probably copper) using the lost-wax casting process and then plated it in silver.
The inside of the band contains his personal hallmark--a musical note struck by an arrow. The musical note was incorporated because playing music was one of his favorite pastimes while the arrow could represent his love for Bonnie or be referring to his last name, Barrow.
The ring, recovered in the couple’s 1933 Ford Model B after the “Sowers Raid” in Texas in 1933, is estimated to sell for at least $40,000.
“The ring is an absolutely amazing artifact of enormous significance,” said Livingston. “It is the closest thing Bonnie and Clyde shared between each other to a wedding ring.”
Another highlight in the June 24 sale is the diamond-studded pocket watch (pictured above) once owned by Chicago’s most infamous gangster, Al Capone.
Known to be a well-dressed man, Capone loved flashy suits, large pinky rings and diamonds.
“Unlike his more-maligned moniker of ‘Scarface,’ Capone preferred that those closest to him call him by ‘Snorky,’ a slang term that meant sharp or well dressed,” Livingston said.
The Illinois Watch Company made Capone’s pocket watch. The bezel is set with 72 cut diamonds, and the watch has a platinum face and gold-tone impressed numerals and hands.
The lot also includes the original 12-inch watch chain made of 14-karat white gold.
Capone’s pocket watch expected to go for $25,000 at RR Auction.
The sale also will include original 1933 Parker and Barrow arrest warrants, a 1934 Barrow signed letter with his fingerprints, Sheriff Schmid’s gold and diamond badge, two death masks of American gangster John Dillinger and James “Whitey” Bulger’s Alfred Dunhill aviator sunglasses.
For the full preview of the auction, visit RRAuction.com.
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