Rare Tupac Shakur Letter to Madonna Heads to Auction - Rolling Stone
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Rare Tupac Shakur Letter to Ex-Girlfriend Madonna Heads to Auction

In 1995 prison note, rapper admits that race factored in breakup

In a handwritten prison letter expected to bring over $100,000 at auction, Tupac Shakur confesses to Madonna that he ended their brief romantic relationship because of her race. 

“For you to be seen with a black man wouldn’t in any way jeopardize your career – if anything it would make you seem that much more open and exciting,” the rapper wrote in the note, dated January 15th, 1995 at 4:30 a.m. “But for me, at least in my previous perception, I felt due to my ‘image,’ I would be letting down half of the people who made me what I thought I was. I never meant to hurt you.”

The letter, available to read in full via TMZ, will go up for auction at the Gotta Have Rock and Roll sale, scheduled for July 19th to 28th. Rolling Stone has confirmed the letter’s authenticity. 

In the note, Shakur admits that Madonna shattered his ego when she remarked in an interview, “‘I’m off to rehabilitate all the rappers and basketball players’ or something to that effect.” But the MC also apologizes to the singer, confessing, “Like you said, I haven’t been the kind of friend I know I am capable of being.”

The rapper adds that he’s “grown both spiritually and mentally” – no longer the “young man with limited experience with [an] extremely famous sex symbol.” He extends an offer of friendship and asks Madonna if she’d agree to “speak face to face.” “It’s funny,” he writes. “This experience has taught me not to take time for granted.”

Despite its overall reconciliatory mood, the letter includes several ominous stretches. “If there is any information you can share with me regarding Jack and crew, please do,” Shakur writes. “It could very well be a matter of life and death.” He also warns Madonna to “please be careful,” using his past as evidence of the world’s cruelty. “Everyone is not as honorable as they seem,” he continues. “There are those whose hearts bleed with envy and evil. They would not hesitate to do you harm! Let my 5 bullets be proof of that!”

Shakur died on September 13th, 1996, six days after being fatally shot in Las Vegas in a drive-by shooting.

In This Article: Hip-Hop, Madonna, Tupac Shakur


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