KMEL Summer Jam 1992 - Tupac Shakur

Source: Tim Mosenfelder / Getty

A couple years ago, Madonna randomly revealed to the world she dated Tupac three years prior to his death in 1995. Now, in an old jail letter being auctioned off by Gotta Have Rock and Roll, we find out why they eventually went their separate ways — and part of the issue was Madonna’s race.

It’s difficult to understand the full context of Tupac’s 2 1/2-page confession, as a lot of it’s redacted, but we do know his decision to leave Madonna had a lot to do with her being White, not wanting to let his fans down, and some ridiculous comment she made about “rehabilitating rappers and baseball players” in an old interview. Sounds like Madonna.

Tupac begins, “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. First and foremost, I must apologize to you because like you said I haven’t been the kind of friend I know I am capable of being.”

Following a redacted portion of the letter, the legend continues, “Can u understand that? 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. 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.”

Following yet another redacted portion of his letter, he talks about how much Madonna hurt him in that old interview. “An interview where you said ‘I’m off to rehabilitate all the rappers and baseball 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. “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.”

Tupac goes on to apologize profusely, hoping Madonna will someday understand he was “young” with “limited experience with a extremely famous sex symbol” when he cared about how he was perceived by the world. He offers his friendship and begs her to be careful: “Everyone is not as honorable as they seem. 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!” Read the full letter here.

Tupac was serving time for his 1995 sexual assault case when he penned the letter. A fan accused the rapper of taking “advantage of his stardom to abuse me and betray my trust.” She claimed that though she had consensual sex with Tupac four days earlier, his friends forced themselves on her on the night in question.

As for Tupac dating Madonna, is it a betrayal when a Black man dates a White woman? Sound off.

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