In a 1995 letter Tupac Shakur wrote to his ex-girlfriend Madonna, he explains that one of the reasons he broke off their relationship was that she was white and he was black, and that he didn't want to let down his fans. He also apologizes for doing so, saying they were the actions of "a young man with limited experience with an extremely famous sex symbol."

Tupac and Madonna dated briefly a year earlier, which she confirmed in a 2015 interview with Howard Stern. In the time between their breakup and the letter, Tupac writes that he had "grown spiritually and mentally" and that "it no longer matters how I'm perceived."

The letter, dated January 15, 1995, was written while Tupac was in Clinton Correctional Facility serving time for sexual assault. Here are some excerpts:

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

The next section has been redacted. The letter 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 & 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.

Tupac later refers to an interview Madonna gave in which he claims she said she was "off to rehabilitate all the rappers and basketball players." Apparently hearing that had a strong effect on him.

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

The full letter will be up for auction at Gotta Have Rock and Roll July 19–28. Bidding starts at $100,000. (A previous letter Tupac wrote garnered $170,000.)

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