Few remember that Tupac and Madonna shared a brief romance in the mid-90s. In a newly unearthed letter from jail (where Pac was serving time for a sexual assault charge in 1995) Tupac opens with an apology: “I haven’t been the kind of friend I know I am capable of being.”
Portions of the letter (which is now up for auction) are redacted but Tupac wrote that while an interracial relationship could help Madonna’s career, he worried about hurting his reputation in the eyes of black audiences.
“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,” he wrote. “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.”
Inflammatory statements Madonna made in the press didn’t make matters easier, Pac wrote:
“An interview where you said ‘I’m off to rehabilitate all the rappers & 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. “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…Can you feel me?”
Tupac also explained that his missteps in their relationship reflected the faux pas of “a young black man with limited experience with an extremely famous sex symbol.”
Ominously, the rapper added “I felt compelled to tell you…just in case anything happened 2 me.” He also offered a final warning to the Queen of Pop:
“Please be careful Madonna. Everyone is not as honorable as they seem. There are those whose hearts bleed with envy & evil. They would not hesitate to do you harm! Let my 5 bullets be proof of that!”
Tupac’s letter will go up for auction starting July 19 via Gotta Have Rock and Roll. Bidding will begin at $100,000.