Why Tupac Shakur Ended His Relationship With Madonna, According to Tupac Shakur

A recently unearthed prison letter by the late rapper helps explain his split from the queen of pop.

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Two years ago, Madonna, queen of pop, revealed in an interview that she had briefly dated the rapper Tupac Shakur before his death in 1996. The late rapper’s brother, Mopreme Shakur, confirmed this later in the year—and now, a letter Tupac wrote Madonna from prison, which will go up for auction at the end of July, sheds further light on why they split.

Tupac’s last auctioned letter was sold for more than $170,000, according to TMZ, who published the hand-written letter with sizable portions redacted Wednesday morning. Dated January 15, 1995, time-stamped 4:30 a.m., Tupac’s letter begins with an apology: “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,” he wrote. “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.” He goes on to describe their split as the consequence of how an interracial relationship might impact their respective careers—and especially his. (“Tupac Shakur Confesses in Prison Letter I Dumped Madonna Because She Was White,” read the TMZ headline—a grabby, if reductive take.)

“For you to be seen with a black man wouldn’t in any way jeopardize your career,” he wrote. (Madonna previously told Howard Stern dating Tupac “had got me all riled up about life in general,” so when she went on David Letterman’s show, “I was feeling very gangsta” and started swearing at the late-night host; Tupac also alludes to an interview she gave in the ’90s in which she hinted at dating multiple rappers in addition to Tupac.) “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.”

And while he describes himself as “a young man with limited experience,” the rapper also offers his sage advice, warning Madonna “not everyone is as honorable as they seem.” Their split, judging by the apologetic tone of the letter, was none too amicable, yet by the end of the letter the rapper seems prepared to put it behind them. Tupac closes the letter offering his friendship again to Madonna, admitting he had “grown both spiritually and mentally. It no longer matters how I’m perceived.”

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