In a handwritten letter Tupac penned to Madonna, the late rapper confessed to ending his relationship with the "Material Girl" because she's white.
The 22 year-old letter dated January 15, 1995, shows Tupac in a reflective space where he confesses how he believed their relationship would damage his career and "image."
Madonna confirmed two years ago they had had a relationship, though it is unclear how long it lasted.
The three-page letter is up for auction between July 19-28 by Gotta Have It Rock and Roll, with a starting bid of US$100,000.