“I never meant to hurt you.”

In a handwritten letter penned in prison, Tupac revealed he broke up with Madonna because of societal views on interracial celebrity couples and how that could tarnish his image.

In the revealing letter uncovered by TMZ, which is going up for auction July 19-28 at Gotta Have Rock and Roll with a starting bid of $100k (it’s expected to go for far more), Shakur explained why he felt the need to part ways with the Queen of pop.

“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,” 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.”

Parts of the letter are blurred, but in a section that’s legible, Pac details how Madonna hurt him. “In an interview where you said, ‘I’m off to rehabilitate all the rappers and basketball players’ or something to that effect,” he wrote, “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 and a natural instinct to strike back and defend my heart and ego that I said a lot of things.”

As Rap-Up points out, he also warns Madonna of “evil” people and asks for “any information…regarding Jack & crew.” He adds: “It could very well be a matter of Life & Death.”

Madonna first revealed the news she and Tupac were in a relationship in an interview with Howard Stern in 2015. “One time, I was mad at [David Letterman] when I said the f-word a lot. I was in a weird mood that day,” she said. “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.”

Two other handwritten letters from Tupac have previously been auctioned off. One sold for $35,000, and the other a cool $172,000.

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