We’re left with an oral history pieced together by those who knew them. Madonna hasn’t been forthcoming about the relationship, aside from confirming it.
A recently surfaced letter, written by Shakur to Madonna, offers a rare insight into his life. It appears to be a break-up letter, but it hinted at just how calculated aspects of Shakur’s character were, particularly with regard to race.
The letter was addressed simply to “M” and was dated January 15, 1995, which coincided with his time at New York’s Clinton Correctional Facility for sexual assault. It was first published by TMZ with four sections redacted. Rolling Stone 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, scheduled for July 19-28. In it, Shakur 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,” he 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. Like you said, I haven’t been the kind of friend I know I am capable of being. I never meant to hurt you.”
By his “image”, Shakur was likely referring to his status as an activist and social critic focusing on the perils faced by black communities in the US through his music.
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 colonisers”, according to HipHopDX.
His lyrics were often tinged with anger at the systematic oppression of black Americans.
In the letter, Shakur 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”.
“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. 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.
“I felt compelled to tell you ... just in case anything happened to me,” he wrote. “Please be careful Madonna. Everyone is not as honourable as they seem. There are those whose hearts bleed with envy and evil. They would not hesitate to do you harm.”
Madonna hasn’t said much about her relationship with Shakur, though she told Howard Stern that he was responsible for her 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 said. “I was dating Tupac Shakur at the time. So when I went on the show I was feeling very gangster.”