A Rare Prison Letter From Tupac to Madonna

January 15th of 1995 is the day Tupac sat down at New York's Clinton Correctional Facility and wrote Madonna a letter. The two had met at the Soul Train Music Awards in LA just two years ago, and began their romance in 1994. Not much of this relationship is known to the public, but his letter to Madonna, which he penned whilst in jail for sexual assault, gives the public a bit of insight. 

"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," Tupac recounts in the handwritten letter, which Rolling Stone confirmed the authenticity of."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."

The cause of the resurfacing of the letter is unknown, but it will be auctioned -- with a starting bid of $100,000 -- at the Gotta Have Rock and Roll sale, which will take place from July 19th to July 28th.

Tupac almost mentions that Madonna broke his heart by nodding to an interview in which she said she was dating "rappers" -- meaning more than one of them.

"You said 'I'm off to rehabilitate all the rappers and basketball players' or something to that affect," Tupac said. "Those words cut me deep seeing as how I had never known you to be with any rappers besides myself. It was at this moment out of hurt and natural instinct to strike back and defend my hurt and ego that I said a lot of things."

The rapper's death was announced the following year after a drive-by shooting in Las Vegas, Nevada.