Late rapper Tupac Shakur apparently had plenty of time to reflect while in jail in early 1995: He wrote a letter to ex-girlfriend Madonna explaining the reasons for their breakup, which he said happened partly because she was white, TMZ reports. "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," Tupac writes in the letter, which can be seen here. "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."
Madonna didn't reveal until 2015 that she used to date Tupac, who was killed in a drive-by shooting in Las Vegas in 1996, Mashable reports. In the letter, Tupac tells Madonna he never meant to hurt her, saying, "I must apologize to you because like you said I haven't been the kind of friend I know I am capable of being." He says he has "grown both spiritually and mentally" since their relationship. He also tells her he was hurt by an interview in which she said, "I'm off to rehabilitate all the rappers and basketball players." Auction site GottaHaveRockandRoll.com plans to auction the letter off later this month, with $100,000 as the starting bid. (Another Tupac letter from jail sold for more than $170,000 two years ago.)