Bad Memories

Crystal Harris Sells Hugh Hefner Engagement Ring & More Jewelry Sales

Hugh Hefner’s ex is reportedly auctioning off her engagement ring. See more famous post-split fire sales.

Craig Barritt / Getty Images

Craig Barritt / Getty Images

Hugh Hefner’s ex is reportedly auctioning off her engagement ring. See more famous post-split fire sales.

Craig Barritt / Getty Images

Crystal Harris

As if breaking her 85-year-old fiancé’s heart (and bashing his sexual prowess) wasn’t enough, now Hugh Hefner’s 25-year-old runaway bride is making money off their called-off engagement. Crystal Harris, who left the Playboy founder four days before their planned June wedding, is putting her engagement ring up for auction. Harris reportedly tried to give Hefner back the 3.39-carat rock, but he wouldn’t accept. Now, Christie’s bidders will have the chance in October to own the $90,000 ring—and a piece of Playboy history.

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Elin Nordegren

Tiger Woods' ex-wife Elin Nordegren allegedly wanted to make it known that she was ready to move on from the disgraced golfer; the former Swedish model sold all the jewelry he gave her, The National Enquirer reported in November 2010. She allegedly instructed Sotheby's to auction off all of her charms, which are estimated to be worth $2.5 million—and that's in addition to the $100 million Nordegren received in the divorce settlement. "It's the ultimate act of revenge," an insider told the tabloid. "It's her way of saying, 'Now do you get the message? It's over!'"

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Anne Hathaway

When Hollywood darling Anne Hathaway learned her fiancé, Raffaello Follieri, was a con artist in 2008, she "spent a week in shock at a friend's," she later told W magazine. But after the young actress recovered from the horrible break-up, she was forced get rid of the tangible reminders of Follieri instead of burning or tossing his gifts. Everything Follieri gave Hathaway was surrendered to the United States government two years after they split and her formerly beloved presents (including Rolexes, rings, pendants, earrings, bracelets, and a Louis Vuitton box) were auctioned to the highest bidder, Radar reported.

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Ellen Barkin

Actress Ellen Barkin had many expensive souvenirs from her ex-husband, billionaire businessman Ron Perelman. Though he left her abruptly five years after they wed, Barkin made sure she reaped the benefits from their time together with a Christie's auction that earned her a whopping $20 million in 2006, E! Online reported. She put 103 items on the block, including rubies, sapphires, and pearls from Tiffany & Co., Van Cleef & Arpels, and designer Joel Arthur Rosenthal; the sale exceeded expectations and made history. Barkin's auction marked "the highest single-owner jewelry sale of the past 15 years in the U.S. and also places it among the top four ever worldwide," Rahul Kdakia, head of Christie's jewelry department, told E! The sale earned so much buzz, it was parodied in the Sex and the City movie for a scene in which Carrie Bradshaw and her brood attend a jewelry auction of a wealthy businessman's ex-wife.

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Sarah Brice of The Bachelor

Though Sarah Brice won the heart of actor Charlie O'Connell on The Bachelor's seventh season in 2005, their romance did not last. The two broke up in 2007, reconciled the following year, and then split for good this past April. Despite their separation, ABC producers allowed Brice to keep her $20,000 engagement ring because she stayed with O'Connell for two years (apparently, that's the unofficial reality TV rule), In Touch Weekly reported. In September, the tabloid revealed that the former TV personality decided to auction off the ring on eBay in an effort to gain a sense of closure. "I need to move on, and looking at that ring wasn't helping matters," Brice told the magazine. "It seemed like a bad omen to keep it. It's a gorgeous ring, though, and someone will be very lucky to get it." The starting bid was just $5,000.

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Jennifer Lopez

Ben Affleck and Jennifer Lopez originated the celebrity portmanteau, but the Bennifer romance did not stick like the name. Despite a gaudy engagement ring, the two never made it down the aisle. Affleck gave the "Love Don't Cost a Thing" singer a 6.1-carat pink Harry Winston diamond in 2003 when he asked for her hand in marriage, but the bauble eventually made its way back to the jeweler. In 2005, People magazine reported that Harry Winston reacquired the diamond, which Affleck paid $1.2 million for in 2002. The actor downgraded when he proposed to Jennifer the second, actress Jennifer Garner in 2005—he popped the question with a 4.5-carat Harry Winston diamond ring valued at $500,000. That stone, however, had more staying power—the two are still together.

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Kim Basinger

Kim Basinger met her future husband Alec Baldwin on the set of The Marrying Man in 1990; but after nearly 10 years together, their marriage soured and one of the ugliest custody battles in Hollywood history ensued. Basinger clearly did not want to cherish the ring Baldwin gave her when he asked for her hand in marriage. In 2004, the actress auctioned off the 3.7 carat Tiffany & Co. diamond along with some of her other jewels at Christie's for a good cause, according to Contact Music. The ring brought in $59,750, and a necklace from Baldwin went for $20,315, all of which went to The Performing Animal Welfare Society in California.

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Alison Eastwood

Clint Eastwood's daughter, actress Alison, hasn't been the luckiest in love—her first marriage ended after less than a year, she lost one boyfriend in a snowboarding accident, and last year, she broke up with her millionaire fiancé John Vorzimer. "Things didn't work out in my last relationship," Eastwood told Star magazine in 2009. "I have a new boyfriend, and I'm very happy." After things ended with Vorzimer, Eastwood started dating an artist and was smart about protecting her assets. The up-and-coming star auctioned off her $50,000 engagement ring, explaining to Star, "I didn't know what else to do with it… Hopefully, someone else can get some use out of it!"

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Elizabeth Taylor

The Taylor-Burton Diamond is not just a piece of jewelry—it's a legendary part of Hollywood history. Elizabeth Taylor's fifth husband Richard Burton bought the 69.42-carat pear-shaped jewel from Harry Winston in 1969, after an auction battle with Cartier. Taylor finally famously wore the diamond for the first time to Princess Grace's 40th birthday party in Monaco, after it made its way from New York with two armed guards. After the couple's 1978 divorce—which was just as high profile as the stone-- Taylor announced she was putting the diamond up for sale and donating a portion of the proceeds to build a hospital in Botswana. "It was large and very heavy," Taylor reportedly said. "Anyway, I hadn't worn it for ages. It represented a different phase in my life, the fun and camp phase." A year after her announcement, New York jeweler Henry Lambert bought the Taylor-Burton Diamond for $5 million and quickly sold it to jewel mogul Robert Mouawad, who still owns it.