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For as long as I can remember, there have been rumors about Tupac dating Madonna. And in 2015, the singer told Howard Stern that they were involved before he passed away. Madonna said Rosie Perez introduced them.
Apparently, it came as a surprise to some folks, including fellow rapper A$AP Rocky
While I don’t know the extent of their relationship and whether or not it involved sex (likely), there is evidence from Tupac that not only did they both date, Tupac was the one to break things off with her because of race.
In the letter, obtained by TMZ , the parts that are not redacted read as follows.
” Jan. 15, 1995 4:30 a.m.
M.
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. 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
…
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. 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.
…
An interview where you said, ‘I’m off to rehabilitate all the rapper 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. It was at this moment out of hurt & a natural instinct to strike back and defend my heart & ego that I said alot of things.
…
In the time since, as you can see, 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 a extremely famous sex symbol.
…
I offer my friendship once again this time much 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.
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! Let my 5 bullets be proof of that!
Always,
2PacI 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 funny but this experience has taught me to not take time 4 granted. <3″
Would love to know if she visited him in prison and whether or not they ever communicated after this.
I don’t want to get too in depth with my opinion on his decision. But judging by her insinuation that she was going be the [White] savior for rappers and basketball players and the fact that Madonna called her own son the n-word, in 2014 and didn’t see the problem with it, I’d say things worked out as they were supposed to.
Another letter from Tupac sold for $170,000. It’ll be interesting to see what happens to this one. Honestly, I don’t know how or why Madonna let it go.
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