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Tupac’s Breakup Letter to Madonna Reveals His Struggle with Their Interracial Relationship

Tupac Shakur and Madonna dated in the early to mid-1990s. (Patrick McMullan/Patrick McMullan)

The newest piece of Tupac Shakur memorabilia up for auction provides more insight about his relationship with pop star Madonna and why her whiteness led him to call things off.

“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,” he wrote in the Gotta Have Rock and Roll auction prison letter obtained by TMZ. “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.”

Pac, who wrote the three-page letter addressed to “M” in January 1995, lets Madge know he hasn’t “been the kind of friend I know I’m capable of being,” but also said she wasn’t always kind, either.

“In an interview where you said, ‘I’m off to rehabilitate all the rappers and basketball players’ or something to that effect, those words cut me deep seeing how I had never known you to be with any rappers besides myself,” he wrote in the letter which has some portions blurred out. “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.”

Pac asked Madonna to understand he has “limited experience with [an] extremely famous sex symbol” and offered his friendship to the singer. The rapper concluded by warning Madonna to be wary of “those whose hearts bleed with envy and evil.”

Gotta Have Rock and Roll is selling the letter, which TMZ reported has a starting bid of $100,000, during The Rock and Roll Pop Culture Auction July 19-28. Other Pac items that recently have been on the auction block include the vehicle Shakur was fatally shot in and an essay, which sold for more than $172,000.


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