Wednesday, January 19, 2022

Tupac’s Jailhouse Apology Letter to Ex-girlfriend Madonna Goes to Auction, Starting Bid $100K

Madonna and Tupac (Getty Images)
Madonna and Tupac

*Tupac Shakur’s infamous jailhouse break-up letter to Madonna is going to be auctioned, despite the singer’s objections. 

Gotta Have Rock and Roll obtained the letter from the singer’s former art consultant Darlene Lutz and plans to auction it off to the highest bidder on July 17.

The pop star claimed ownership of the three-page but she legally transferred it to Lutz about 15 years ago, according to a New York Supreme Court ruling last month. Since Lutz owns the letter, she can rightful sell it. 

Madonna attempted to stop the sale two years ago when she told a judge that her celebrity “does not obviate my right to maintain my privacy,” per

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Shakur hand-wrote the three-page letter from prison in 1995 when he was 24. Madonna was 37 at the time. In it, the rap icon explains why the two of them are no longer a good look.  

“I must apologize to you,” he wrote. “Because like you said I haven’t been the kind of friend I know I am capable of being. Not because I am evil or because you weren’t worthy but at the risk of sounding over dramatic, the effects of racism make it difficult for a young black man to properly show affection for an older white woman.”

Pac and Madge dated briefly in the 90s, though they kept their relationship secret.

As noted by RollingStone, Shakur wrote that dating a white woman made him uncomfortable because he “would be letting down” the folks who made him what he was. He also took issue with Madonna allegedly saying it was her job to “rehabilitate all the rappers and basketball players.”

“Those words cut me deep seeing how I had never known you to be with any rappers besides myself,” he wrote. “It was at this moment out of hurt and a natural instinct to strike back and defend my heart and ego that I said a lot of things I have since come to regret.” 

Pac reportedly wrote the letter while he was serving nine months in prison for sexual assault.

He noted that part of the reason he wanted to write her was because he wanted to tell her how he felt “in case anything happened 2 me,” adding that “everyone is not as honorable as they seem … let my five bullets be proof of that.”

The memorabilia company estimates the letter will sell for up to $300,000. The minimum bid is $100,000. Partial proceeds from the sale will go to

Ny MaGee
Ny MaGee is an entertainment reporter with over 15 years of experience working in the film industry in areas including production and post-production, marketing, distribution, and acquisitions. She has worked for legendary film producer Roger Corman, Quentin Tarantino's production team at Miramax, the late Larry Flynt, MTV/ VH1, Hallmark Channel, Paramount, Jim Henson Co., Parade Magazine, and various LA-based companies representing above-the-line talent.



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