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Madonna’s underwear, sold for the very first time

Early one January morning in 1995, Tupac Shakur composed a letter to Madonna from a cell in Clinton Correctional Facility, in upstate New York. “M, I’ve waited a long time 2 finally write this mainly because I was struggling to find all the answers so that I wouldn’t leave any unanswered questions,” it began. In cramped scrawl, Shakur outlined his reasons for ending their romance the year before. “At the risk of sounding overdramatic, the effects of racism make it difficult for a young black male to properly show affection for an older white woman. Can U understand that?” he implored. “I never meant to hurt you.”

Even after Shakur’s murder in 1996, hardly anyone knew he and Madonna had dated — until 2015, when the queen of pop spilled the beans to Howard Stern. A few years later, the letter Shakur wrote the pop star from prison appeared online when the celebrity memorabilia auction house Gotta Have Rock and Roll listed it for sale alongside all sorts of Madonna-adjacent ephemera. One lot offered the star’s personal checkbook with a handwritten ledger. Another item for sale was a “personally owned” brush containing strands of her hair. There were photos and negatives of her dancing with male strippers at a bachelorette party, lingerie she’d performed in onstage, a pair of panties she’d mailed an old flame, and an array of private correspondence — including the letter from Shakur.

Excerpt from Tupac’s love letter to Madonna. Gotta Have Rock and Roll

The celebrity memorabilia market is staggeringly lucrative. Auction house proprietors estimate profits have grown tenfold in the last decade, from $20 to $40 million to $200 to $400 million, according to The Hollywood Reporter. Fame infuses the detritus of celebrities’ lives with collectible value — and celebrities themselves certainly profit off this dynamic. Their fandoms fuel ticket sales, album sales, promotional deals, and every other machination of the entertainment industry.

Madonna is one of the richest women in music, worth $570 million according to Forbes. Still, the Madge memorabilia for sale in the auction was incredibly personal. You can’t just replace letters from a dead lover. What’s more, the woman who consigned the items was a former member of Madonna’s entourage who allegedly came into possession of them by scandalous means. “Madonna’s secret love letter from Tupac in prison” is the stuff of TMZ fantasy, but unlike someone like Elvis, for example, Madonna’s still around to cherish her mementos and to feel violated when strangers legally, but perhaps immorally, come into their possession. When it comes to famous people and the ways we idolize them, where do we draw the line between people and profit?

Madonna caught wind that her stuff was up for auction through tabloid coverage and sued, claiming it was stolen by her former friend and art advisor, Darlene Lutz. A judge issued a temporary restraining order halting the sale of the most intimate items while the case wound its way through the justice system. As the story goes, Madonna and Lutz had once been close friends before falling out in 2004, over four missing paintings collectively worth $500,000. Lutz said she sold them to a collector at Madonna’s behest, but after the art was already delivered, the singer changed her mind and wanted them back. “I said, ‘No.’ The deal had already been done,” Lutz told Artnet.

But according to Madonna, Lutz was cagey about the paintings’ whereabouts from the beginning. (To this day, it’s never been revealed what exactly happened to them.) She stopped answering emails, which led to speculation in Madonna’s circle about Lutz’s physical and mental health, according to messages presented as evidence in court. The singer sued, and the parties wound up settling. Lutz paid Madonna a lump sum for the lost art, and in return, the star signed a broad general release — fairly standard legalese saying Madonna wouldn’t go after Lutz for any past grievances with future litigation.

What the singer didn’t know when she and her art advisor severed ties was that Lutz had been quietly amassing a collection of Madonna memorabilia for decades — old costumes Lutz bought for the struggling singer in the early days, junk Madonna asked to store during a move, correspondence from friends and family and an old flame, evidently. Flash forward to the case involving the Shakur letter: citing the 2004 settlement agreement, the Supreme Court of New York ruled Madonna’s stuff belonged to Lutz, since it’d been collecting dust in her apartment before the star signed her rights away with that release. Lutz could do whatever she wanted with it, and she wanted to sell. On July 17, 2019, Gotta Have Rock and Roll’s listing for Lot #2: “Tupac Shakur Handwritten Signed Love Letter to Madonna from Prison” went live with a minimum starting bid of $100,000.

“Why shouldn’t I be able to make money off this? When did it become a sin to make money?”— Darlene Lutz, former Madonna associate

“There was a lot of litigation for a case that didn’t seem to really go anywhere,” observed Jeremy S. Goldman, a Los Angeles–based entertainment lawyer I enlisted to help unpack legalese around the Shakur letter. Goldman explained the case was decided on a technicality: the 2004 settlement agreement released Madonna’s claim over any property, known or unknown, that Lutz still had in her possession. It was “like they got divorced,” he said. “What’s yours is yours and mine is mine.” The court also noted that the statute of limitations for claiming stolen property had long passed.

Goldman told me that when parties settle, the terms of a general release are usually subject to intense negotiation. California actually has a law protecting people from signing away their right to property they’re not aware of. Goldman thought the 2004 release between Lutz and Madonna, which was executed in New York, seemed oddly broad. The singer probably assumed whatever she signed only addressed her missing paintings. “At the time, I was just thinking about getting money back that she had secretly tried to get away from me. […] I wasn’t thinking about personal items,” the singer testified in a 2017 deposition.

Unfortunately, intent doesn’t hold up in court. The judge’s job, according to Goldman, was to determine whether Madonna gave up possession of the Shakur letter. “If she did, then it belongs to Lutz,” he said. “And that happens all the time, you know? The fact that it has sentimental value to Madonna is irrelevant under the law.”

The pat legal ending to the story of the Shakur letter leaves a lot of loose threads. Goldman told me over the phone that he thought Madonna never got her day in court. “She never got to make her case that, ‘I own this stuff, and [Lutz] stole it from me, and she doesn’t have the right to sell it.’” In July, Lutz was blunt about it in an interview with Artnet. “Why shouldn’t I be able to make money off this?” she said. “When did it become a sin to make money?”

The 1970 Metro-Goldwyn-Mayer studio auction was the first significant sale of Hollywood paraphernalia. On the brink of bankruptcy, MGM decided to liquidate seven warehouses’ worth of costumes, props, and other leftovers from the golden age of filmmaking. The studio sold everything to a prescient auctioneer named David Weisz for just $1.5 million; Weisz then turned around and staged a sale that recouped eight times what he’d paid.

To prepare for his auction, Weisz recruited Kent Warner — a costumer with a colorful reputation for plucking items with interesting provenance from the trash — to sift through more than 350,000 dusty garments in MGM’s archive. He unearthed the most famous treasure in the studio’s trove: the ruby slippers worn by Judy Garland in The Wizard of Oz.

More than 6,000 people bought tickets to the auction for $100 each (if they bought something, the admission fee was refunded). The sale consisted of so many items that it was actually a series of daily auctions that went on for nearly three weeks. In 1970, the Los Angeles Times characterized it as “an 18-day wake for Hollywood.” Celebrities like Rock Hudson and Shirley Jones peppered the crowd vying to get a peek at MGM’s treasures. Actress Debbie Reynolds bought thousands of items from Weisz and spent $180,000; it was the beginning of a film memorabilia collection that would fetch her $22.8 million in 2011.

“MGM just wanted to sell off all that and didn’t think it had any value, even the ruby slippers,” said Leo Braudy, a pop culture historian and fame expert who teaches at the University of Southern California. “They didn’t realize that there was this huge potential fan base out there willing to pay a fair amount of money for a lot of the stuff.”

These days, celebrity memorabilia is considered as sound an investment as fine art. “I had a client one time who bought a really important guitar, and he said, ‘It’s a lot sexier to hang John Lennon’s guitar on my office wall than it is a Monet,’” said Darren Julien, the founder of Julien’s Auctions, a high-end purveyor of entertainment ephemera.

Madonna’s the biggest icon there is. I think there’s her and Marilyn Monroe, and when it comes to music, no one comes close.”— Ed Kosinski, the founder of Gotta Have Rock and Roll

In 2016, Julien’s Auctions sold the dress Marilyn Monroe wore to croon “Happy Birthday, Mr. President” to John F. Kennedy for $4.8 million, making it the most expensive dress ever auctioned. “Marty Zweig, who was a big Wall Street guy, he bought it from Christie’s in 1999. He paid $1.26 million for it, and it was a world record for a dress at the time,” Julien said. “The press asked him, why did he spend that much on a dress? He said, as an investment. And they all laughed and thought he’d gone nuts.”

The most valuable stuff on the market once belonged to dead celebrities, mostly, like Monroe, Elvis Presley, John Lennon, and Elizabeth Taylor. But when it comes to living legends, you might say Madonna’s in a league of her own. “Madonna’s the biggest icon there is,” Ed Kosinski, the founder of Gotta Have Rock and Roll, told me. “I think there’s her and Marilyn Monroe, and when it comes to music, no one comes close.”

In 2014, Julien’s Auctions sold the jacket Madonna wore in the 1985 film Desperately Seeking Susan for $252,000. One short-lived hedge fund, Marquee Capital, actually claimed 80 percent of its assets were invested in Madonna memorabilia in 2008. People have also tried making a buck off Madonna’s literal dirty laundry a number of times. Ten years ago, Gotta Have Rock and Roll auctioned explicit faxes, voicemails, and a video the star sent her bodyguard-turned-lover, Jim Albright, between 1992 and 1994. “I think there were two pairs of panties in that collection,” Kosinski told me. Madonna’s lawyers contacted him in 2009 but didn’t file suit.

Kosinski was quick to justify profiting off Madonna’s personal relationships on her notorious public persona. “All you gotta do is [look up] ‘David Letterman,’” he said, referencing Madonna’s infamous, profanity-laden appearance on “The Late Show” in 1994. It’s the one where she calls Letterman a “sick fuck,” gives him a pair of her underwear, then asks, “Wait a minute, aren’t you going to smell them?”

Selling a woman’s underwear — even if she gave them to someone, even if she’s famous — is objectively skeezy. But the panty posturing on Kosinski’s behalf gives you a sense of the moral bargains people seem willing to make in order to profit off a brush with fame. “There’s a certain kind of weird freakiness about it. A certain kind of whimsy, almost,” Braudy said, of the impulse to collect a stranger’s intimately personal objects. “In the same way that a saint’s finger bone or robe could have a special place in a church, […] this is like a secular version of that. This object is an intermediary between me and the star.”

Plenty of fans have gone to kooky lengths to get close to the celebrities they idolize. In the early ’70s, a self-described “Dylanologist” named A.J. Weberman got famous for going through Bob Dylan’s garbage and studying it like a scientist. The singer got sick of the snooping and assaulted him on Elizabeth Street in 1972. “I deserved it,” Weberman told The New York Times in 2006. “I don’t hold it against him.” In 2010, an X-ray of Marilyn Monroe’s chest was auctioned for $45,000. In 2016, Julien’s Auctions sold Truman Capote’s ashes for the same amount. They came in a cardboard box affixed with a label from the crematorium.

Another lot listed alongside the Shakur letter and Madonna’s stuff in the Gotta Have Rock and Roll auction caught my eye: an ultrasound photo of Frances Bean Cobain from 1992 and a card scrawled with baby names in Kurt Cobain’s handwriting. “Frances” is near the top of the list.

It struck me as an intensely personal memento, and I wondered how it wound up on the market. Kosinski told me it was consigned by a collector who’d bought it at another auction in the early 2000s. (It’s unclear how the ultrasound ended up in the first auction.) “They had their own children and they no longer wanted it,” he said. That such an intimate family treasure could be so casually offloaded from one stranger to another seemed cruel. Of course, if they really wanted the ultrasound, Frances Bean and her mother Courtney Love are wealthy enough to buy it back — Kurt’s estate is worth an estimated $450 million. And maybe they did reclaim it; Gotta Have Rock and Roll doesn’t share its buyers’ identities.

Frances Bean is more familiar than most with the crazy things people will do in the name of Nirvana idolatry. In recent years, she and her ex-husband Isaiah Silva have been engaged in a very public dispute over one of her father’s most famous guitars — the 1959 Martin he played on MTV Unplugged in November 1993. It’s reportedly worth millions, and it was the sole object the court awarded Silva after the couple split in 2016. Frances Bean fought hard to keep the guitar in her family’s possession; she filed documents asserting Silva shouldn’t be entitled to any part of her father’s estate and asked the judge to award her all her premarital assets as separate property. The Martin was the one thing to slip through Frances Bean’s grasp.

Reporting this story was an intoxicating IV-drip of obscure celebrity trivia that I regaled many kind strangers with at parties. But at the glitzy core of this story is a pretty sad story of what happens when people are treated like commodities.

Things got really weird in May 2018, when the news broke that Silva was suing his former mother-in-law for conspiring to murder him. He alleged that Love, her manager Sam Lutfi, actor Ross Butler, and others were in on an elaborate plot to do away with him and reclaim the guitar. This summer, Page Six reported that Love is pushing for Silva to undergo a psychiatric evaluation, in an attempt to prove he’s not of sound mind. In 2018, a source close to the family revealed that Frances Bean’s ex harbors a “frightening obsession” with her father, may believe he’s “a reincarnation of Kurt,” and tries to look and dress like him.

The entire saga, just like the Shakur letter, makes excellent tabloid fodder. Reporting this story was an intoxicating IV-drip of obscure celebrity trivia that I regaled many kind strangers with at parties. But at the glitzy core of this story is a pretty sad story of what happens when people are treated like commodities. Many celebrities owe their careers to giving fans access to their private lives, but navigating the line between the personal and professional is rarely simple. “It’s a kind of negotiation, and there are celebrities who can deal with it better than others,” Professor Braudy said. There are some who “can give the paparazzi and the fans what they want, and at the same time maintain a kind of moat around other parts of their lives.” These days the divide is even fuzzier, thanks to the access offered by social media.

It’s also pretty difficult for celebrities to protect their everyday stuff, according to the experts I talked to. “Shockingly, celebrities are just people. They use hairbrushes, they write letters, and live their life. They come into possession of things and wear outfits and underwear. From a practical angle, I don’t think people are going to be able to do much to protect those kinds of things,” Goldman said. Demanding your entire entourage sign a comprehensive NDA that holds them responsible if things go missing is one option, he said, but it comes with obvious logistical drawbacks.

The icky feelings around who’s allowed to sell a celebrity’s stuff largely falls along the lines of who’s still around to care about it. Few people object to Elizabeth Taylor’s estate partnering with Julien’s Auctions to sell her jewels and fancy automobiles. Because Madonna is still around to personally appreciate a letter from her dead lover, it chafes that someone else gets to decide its fate. Same with Kurt Cobain’s guitar and the ultrasound from 1992: Frances Bean wasn’t even two when her dad passed.

“Different people have different philosophical perspectives on what constitutes fair financial transactions,” Hersh Shefrin, a pioneer of behavioral finance and professor at Santa Clara University, explained. Madonna viewed it as highly unfair Lutz was selling her items; Lutz thought she acquired them fair and square. “Did [Madonna] sign them away because she wasn’t paying attention? Were there other circumstances at the time? We just don’t know,” Shefrin added. “And without knowing that, it’s really hard to make an ethical determination […] whether somebody’s being fair or not.”

The Gotta Have Rock and Roll auction featuring the Shakur letter closed at the end of July. Someone paid $1,391 for the bachelorette photos. An unreleased recording of “Like a Prayer” on cassette fetched $3,670. The singer’s personal checkbook sold for $1,044. Frances Bean’s ultrasound went for $5,000.

But no one placed a single bid on the Shakur letter. For now, it’ll remain in Lutz’s hands — fair game for an institution, a fan, or even Madonna herself to make the art advisor an offer she can’t refuse.