A Recently Surfaced Letter Shows That Race Played a Role in Tupac and Madonna’s Break-Up

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Madonna first mentioned her 1995 relationship with Tupac in 2015 (Getty)

Back in early March of 2015 Madonna was a guest on The Howard Stern Show and made some news when she casually mentioned once dating the late Tupac Shakur. Stern had asked her about her infamous appearance on The Late Show with David Letterman, in which she ignored a lot of Letterman’s questions, swore a few times and dropped some sexual innuendos. Talking to Stern, Madonna said Tupac, who was killed in 1996, was partially responsible for her behavior, saying that the two were dating at the time.

The comments didn’t get much traction back then, but now a recently surfaced letter Tupac wrote to Madonna has created a renewed interest in their relationship. The note, written while the rapper was in prison for sexual assault, looks to be a break-up letter. TMZ first published the letter on Wednesday, with Rolling Stone confirming it’s authenticity shortly after.

In the letter, addressed to “M,” it looks as if Tupac was breaking up with Madonna because she was white, writing that her being with him wasn’t the career-jeopardizing move that it could be for him.

“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 wrote. “But for me at least in my previous perception I felt due to my ‘image’ that I would be letting down half of the people who made me what I thought I was.”

Possibly playing a role in Tupac’s motivation was his background. His parents were both Black Panthers in New York City and his godfather and stepfather were Black nationalists, fighting to support African Americans who felt oppressed in America. Tupac was named after Tupac Amaru, a South American revolutionary. Tupac also routinely addressed racial issues in songs like “Words of Wisdom.”

“Emancipation Proclamation? Please! / Lincoln just said that to save the nation / These are lies that we all accepted / Say no to drugs but the governments’ kept it / And yet, they say this is the Home of The Free / But if you ask me, it’s all about hypocrisy.”

Also in the letter, Tupac said he felt hurt by comments Madonna had made in an interview, in which she said “‘I’m off to rehabilitate all the rappers and basketball players’ or something to that effect.” The letter concludes with a somewhat haunting and ominous few lines.

“Please be careful Madonna. Everyone is not as honorable as they seem,” he continues. “There are those whose hearts bleed with envy and evil. They would not hesitate to do you harm! Let my 5 bullets be proof of that!”

The letter is scheduled to be sold at the Gotta Have Rock and Roll auction July 19th through the 28th. It is expected to fetch at least $100,000.

You can read the full letter here, via TMZ.