Tupac’s relationship with Madonna was a little more complicated than any of us realized.
Back in 2015, Madonna made headlines after sharing that she had dated the rapper just three years prior to his death in 1996. She revealed in an interview with Howard Stern, “One time I was mad at David Letterman when I said the f-word a lot, but the rest of the time was good. I was in a weird mood that day and 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 gangsta.”
The same year, the rapper’s brother, Mopreme Shakur, told Vlad TV that he assisted in igniting the romance. Reportedly, Madonna gave Mopreme a note and it started out as business. Mopreme said that he was driving Tupac to her house in Los Angeles for some time after that.
TMZ recently published pieces of a letter written by Tupac on January 15, 1995, to Madonna while in jail for sexual assault at Clinton Correctional Facility. The letter will be auctioned off this month with a starting bid at $100,000. The last letter written by Tupac was sold for more than $170,000.
The note called Madonna “M” and said, “I’ve waited a long time 2 finally write this mainly because I was struggling to find all the answers that I wouldn’t leave any unanswered questions. First and foremost, I must apologize to you because like you said I haven’t been the kind of friends I know I’m capable of being.”
He continued by explaining that he ended his relationship with Madonna simply because of her race.
“Can u understand that? 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 & exciting. 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. I never meant to hurt you.”
Tupac then referenced an interview where apparently Madonna said that she would “rehabilitate” all the rappers. Tupac responded, “Those words cut me deep seeing how I had never known you to be with any rappers besides myself. It was at this moment out of hurt & natural instinct to strike back and defend my heart & ego that I said a lot of things. Can you feel me? In the time since, as u can seem I have grown both spiritually and mentally. It no longer matters how I’m perceived. Please understand my previous position as that of a young man with limited experience with an extremely famous sex symbol.”
The hip-hop artist wrote later in the letter, “I offer my friendship once again this time my stronger & focused. If you are still interested I would like to further discuss this with you but some of it couldn’t wait. I felt compelled to tell you… just in case anything happened 2 me. Please be careful Madonna. Everyone is not as honorable as they seem there are those whose hearts bleed with envy & evil. They would not hesitate to do you harm! Let my 6 bullets be proof of that!”
The final message read, “I don’t know how you feel about visiting me but if you could find it in your heart I would love to speak face to face with you. It’s finny but this experience has taught me not to take time 4 granted. ”