How high the bidding goes will reflect Bulger’s fame, as ticket sales for Black Mass did. John Gotti, Al Capone, and Bernie Madoff have all experienced similar fates. But the Madoff asset auction hosted by the Marshals Service included many items of high intrinsic value, including a 10-carat diamond ring and a Steinway grand piano. A revolver owned by Capone went for more than $100,000 at a Christie’s auction in 2011.

Firearms would surely bring in the bucks, but federal law prevents the Marshals Service from selling them. Bulger owned a variety of Nazi memorabilia—excluded from the auction—whose value wasn't disclosed. Other items, like toilet paper and undergarments, were also excluded. Instead, Bulger will be proving his notoriety one sweatsuit at a time.

The biggest-ticket items at the Bulger auction are two rings, one a 14-karat gold, three-carat diamond Claddagh ring and the other a sterling silver ring known as the Psycho Killer Skull, which will start at $11,370 and $4,450. When Bulger set about taking control of South Boston, he is alleged to have killed members of the rival Mullen Gang, who were known to wear Claddagh rings, according to crime reporter T.J. English, who wrote the Irish mob history book Paddy Whacked.

“In the universe of Whitey Bulger, the Claddagh ring symbolizes being a victim of Bulger’s. That is one thing about Bulger, given his story and the violence and the disappearance of bodies," he ventured. “Some of these items to me would have bad karma.”

Juju aside, the jewelry is expected to be hot at auction. The celebrity clout offers at least a 20 percent price boost but can often drive prices up more than 1,000 percent, said Leila Dunbar, who runs an appraisal business in Washington, D.C. “No one can quantify passion or emotion. It’s the celebrity value that’s placed by the bidders that day, their connection, what they want to have,” she said. “Everything boils down to an emotional connection.”

Even some household items can make that connection for mob enthusiasts. The Mob Museum, in Las Vegas, is considering purchasing several lots of Bulger’s clothing to recreate an outfit the killer might have worn on the run. Geoff Schumacher, director of content, said the museum would purchase only used clothing, if anything.

“A pair of shoes that were seized from that condo, that were clearly worn by the occupant of that condo, Whitey Bulger, will be more valuable than ones he never took out of the box,” he said. “You’re drawing a direct connection to a guy that was charged with killing 19 people. It’s a more visceral connection.”

As for Greig's items, such as turtlenecks, a straw visor, and more than two dozen pairs of sunglasses, experts agree they’re likely to draw the least attention, though she was on the run with Bulger and charged with harboring a fugitive. “She was the person that essentially kept this secret along with him,” Schumacher said. “But when you look at the actual objects that she had, they were the kind of stuff that my wife or any other middle-aged housewife might have.”

The auction will probably alienate Bostonians who spent years living in fear of the local mafia. Julien, the auction house owner, said even diehard memorabilia buyers have been put off by auctions of O.J. Simpson collectibles, declining to bid up prices.

English, the crime reporter, said the auction could end “the cult of Bulger,” which has turned the cold-hearted killer into a movie star more than once. The sale symbolizes “a fetish of a guy who was a violent sociopathic criminal but a fascinating character,” he said, its wares “meaningless other than what people input into these items. Why someone would want a pair of old sneakers is beyond me. But when you have Whitey Bulger’s pair of sneakers ….”

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