In place of a firsthand account, we’re left with an oral history pieced together by those who knew the couple. Madonna herself hasn’t been particularly forthcoming about the relationship, aside from confirming it and offering a few scant details in 2015.

However, a recently surfaced letter, written by Tupac to Madonna, offers a rare insight into the late rapper’s life. It appears to be a break-up letter, but it hinted at just how calculated aspects of Tupac’s character were, particularly with regard to race.

AD

AD

The letter was addressed simply to “M” and was dated Jan. 15, 1995, which coincided with his time at New York’s Clinton Correctional Facility for sexual assault. It was first published Wednesday by TMZ with four sections redacted. Rolling Stone said it confirmed the letter’s authenticity.

It will be up for auction with a starting bid of $100,000 at the Gotta Have Rock and Roll sale, which is scheduled for July 19 to 28. It was uncertain how the letter wound up in circulation.

In it, Tupac seemed to admit to breaking up with Madonna because she was white.

“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.”

AD

AD

“Like you said, I haven’t been the kind of friend I know I am capable of being,” he wrote, adding, “I never meant to hurt you.”

By his “image,” Tupac was likely referring to his status as an activist and social critic focusing on the perils faced by America’s black communities through his music.

“I’m not saying I’m gonna change the world, but I guarantee that I will spark the brain that will change the world,” he once said.

His parents were both Black Panthers, and he was named for “Túpac Amaru, a South American revolutionary who led an uprising against his imperial Spanish colonizers,” according to HipHopDX.

His lyrics were often tinged with anger at the systematic oppression of black Americans. On “Words of Wisdom,” for example, he rapped:

AD

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

In the letter, Tupac also alluded to being hurt because Madonna in an interview said “’I’m off to rehabilitate all the rappers and basketball players’ or something to that effect.”

AD

“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.”

“It no longer matters how I’m perceived,” he wrote. “Please understand my previous position as that of a young man with limited experience with a extremely famous sex symbol.”

Though the note was conciliatory — he offered “my friendship once again, this time much stronger and focused” — it took an ominous turn at the end.

AD

“I felt compelled to tell you … just in case anything happened to me,” he wrote, adding, “Please be careful Madonna. Everyone is not as honorable as they seem. There are those whose hearts bleed with envy and evil. They would not hesitate to do you harm.”

AD

Tupac was killed in a drive-by shooting the next year.

Madonna hasn’t said much about her relationship with Tupac, though she did once tell Howard Stern that he was responsible for her now infamous interview on “The Late Show with David Letterman” during which she used profanity, sexual innuendo and ignored several of Letterman’s questions.

“I was in a weird mood that day,” Madonna told Stern of the interview. “I was dating Tupac Shakur at the time, and he had got me all riled up about life in general. So when I went on the show I was feeling very gangster.”