Madonna and Tupac Madonna and Tupac

The letter, dated January 15, 1995, 4:30am, confirms Madonna's revelation in an interview in 2015 with Howard Stern about her relationship with the rapper. Written a year before Tupac was fatally shot, the three-page letter raises issues of race and sexuality in their relationship.


"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," the rapper wrote whilst serving time in the Clinton Correctional Facility. "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 goes on to explain the pressure he felt dating someone with the celebrity and sexual prowess of Madonna: ''Please understand my previous position as that of a young man with limited experience with [an] extremely famous sex symbol.''


He ends the letter warning Madonna to be mindful of those around her and the perils of surrounding herself with untrustworthy characters. The rapper also made it clear that he wanted an amicable parting from Madonna, ''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 funny but this experience has taught me to not take time 4 granted.''

Gotta Have Rock and Roll will be auctioning the certified letter from July 19 to 28, 2017, with a starting bid of $100 000. At the end of last year a four-page letter, handwritten by Tupac from a prison cell in 1995 to Nina Bhadreshwar of Deathrow Records sold for $172 750 at Goldin Auctions in Runnemede, N.J.