Rap legend Tupac Shakur broke off a hush-hush fling with Madonna two decades ago because he thought dating the white pop star would hurt his image with his fans, a letter reveals.

The brief relationship between the two music icons only emerged two years ago, and now an auction house has put up for sale a 1995 letter from Tupac, who was shot dead just a year later, to Madonna in which the rapper breaks off the romance.

“For you to be seen with a black man wouldn’t in any way jeopardise your career, if anything it would make you seem that much more open and exciting,” Tupac wrote neatly on lined paper.

“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,” he wrote.

Tupac was apparently referring to his newfound status as a leading voice in hip-hop, with his songs frequently taking on police brutality and other issues of concern to many African Americans.

In the letter, he told Madonna he had read an interview in which the pop great 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,” Tupac wrote.

The letter, first reported by the gossip site TMZ, will go on the block later this month at New York auction house Gotta Have Rock and Roll.

Shortly after the split with Madonna, Tupac went to prison on charges, which he denied, of sexually assaulting a woman in a hotel room.

Tupac, who left prison with an increasingly gangsta image, was killed the following year at age 25 in a still murky shooting in Las Vegas.

The relationship between the two music icons was not widely known until 2015 when Madonna, usually known for her openness, explained a foul-mouthed appearance two decades earlier on David Letterman’s late-night television show.

“I was dating Tupac Shakur at the time and, the thing is, he got me all riled up on life in general. So when I went on the show I was feeling very gangsta,” she told radio host Howard Stern.

Madonna in 1998 began to date English director Guy Ritchie, to whom she was married for eight years. She recently complained that she faced a double standard as a woman for taking younger lovers.

Tupac was engaged at the time of his death to designer Kidada Jones.

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Ali Taherian
A man who loves fashion more than life itself. Always well-dressed and ready to shine.

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