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 4:30am. “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.”

Find out more about the letter and auction here.

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