Tupac Shakur's Prison Letter Explains Why He Ended Relationship With Madonna

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Madonna revealed the three-year romance during a 2015 interview with Howard Stern.

Decades after Tupac Shakur and Madonna's relationship ended, new details are coming to light.

In a letter Tupac wrote to Madonna on Jan. 15, 1995 while serving time for sexual assault at Clinton Correctional Facility, the rapper explained why he called things off with the "Like a Virgin" singer. The letter will be auctioned off by Gotta Have Rock and Roll between July 19 and 28 with a starting bid of $100,000. 

RELATED: Madonna Tells Howard Stern She Dated Tupac

"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 am capable of being," Tupac wrote, later explaining that he broke up with Madonna 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," he shared. "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."

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Tupac later referenced an interview where Madonna supposedly said, "I'm off to rehabilitate all the rappers & basketball players."

"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 a lot of things," he said. "Can you feel me? In the time since, as u 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 an extremely famous sex symbol."

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"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," he continued. "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 5 bullets be proof of that!"

"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," Tupac concluded the letter. "It's funny but this experience has taught me to not take time 4 granted."

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Madonna revealed in a 2015 interview with Howard Stern that she had dated Tupac, who was fatally shot in 1996, for three years.

"One time I was mad at [David Letterman] when I said the f-word a lot, but the rest of the time was good," Madonna revealed. "I was in a weird mood that day. I was 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."

RELATED: 2017 Rock and Roll Hall of Fame Inductees Include Tupac, Pearl Jam

The rapper's brother, Mopreme Shakur, confirmed the romance to Vlad TV later that year, revealing that he helped facilitate their relationship. 

"She gave me a note to give to him; I was just happy she was giving him a note. Everybody was there. I went over and gave it to him. He was about the business and then they linked up. I would take him to her house and s**t when we got back to L.A.," he recalled. "They were a thing for a minute."

See more in the video below.