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Tupac's relationship with Madonna ran deeper than anyone knew.

In 2015, the Material Girl made headlines after revealing she had dated the rapper three years before his death in 1995. "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 told Howard Stern. "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." Later that year, the rapper's brother, Mopreme Shakur, told Vlad TV he helped facilitate the romance. "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. Yeah..." he recalled. "They were a thing for a minute." (In 2014, Rosie Perez told Wendy Williams she played a role in introducing the former couple.)

On Wednesday, TMZ published portions of a letter—written Jan. 15, 1995 at 4:30 a.m.—that Tupac wrote to Madonna while serving time for sexual assault at Clinton Correctional Facility. Gotta Have Rock and Roll will auction off the letter between July 19-28 with a starting bid of $100,000; according to TMZ, the last letter written by the rapper fetched more than $170,000.

Madonna, Tupac

Patrick McMullan/Patrick McMullan via Getty Images

TMZ redacted four chunks from Tupac's letter. The late rapper started by calling Madonna "M," saying, "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."

Later in the letter, he explained that he broke up with the "Human Nature" singer 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 wrote. "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 went on to reference an interview where Madonna had supposedly said, "'I'm off to rehabilitate all the rappers & basketball players,'" or something like that. "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." After another redacted paragraph, Tupac continued to share his side of the story with Madonna. "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," he said. "Please understand my previous position as that of a young man with limited experience with an extremely famous sex symbol."

Later in the letter, the hip-hop heavyweight wrote, "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."

Tupac ended his letter with a warning for the Queen of Pop. "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!" Tupac wrote. "Let my 6 bullets be proof of that!"

After signing the letter, he added a final message: "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, who was fatally shot, said. "It's funny but this experience has taught me to not take time 4 granted."