The surprising relationship between Madonna and Tupac Shakur began with the passing of a note and it apparently ended with one as well. 
 
 Back in 2015, Madonna revealed that she used to date Tupac, and Wednesday TMZ reports that a break up letter Tupac wrote to her in jail has surfaced. 
 
 In 1995, Tupac wrote that his relationship with the renowned singer might negatively affect his public image. 
 
 "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. 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 letter also implies that the two had a falling out after Tupac quotes Madonna as saying, "I'm off to rehabilitate all the rappers and basketball players." Tupac apologizes for anything hurtful he might have said, saying since then he had "grown both spiritually and mentally" and that he was just a "young man with limited experience with an extremely famous sex symbol." 
 
 According to TMZ, the letter will go up for auction starting July 19 at Gotta Have Rock and Roll with a starting bid of $100,000. 
 
 The poignant message can be read in full here. 
 
 Famous people may deal with some different relationship problems than everyday folk, but Tupac's letter shows that everyone has insecurities and doubts — even legendary rappers with legendary pop girlfriends. 
 
 It also shows that Tupac had some great handwriting. ||||| Starting in 1996, Alexa Internet has been donating their crawl data to the Internet Archive. Flowing in every day, these data are added to the Wayback Machine after an embargo period. ||||| Tupac Shakur Confesses in Prison Letter I Dumped Madonna Because She Was White 
 
 Tupac Confesses in Prison Letter He Dumped Madonna Because She Was White 
 
 EXCLUSIVE 
 
 Tupac broke off his sexual relationship with Madonna because she was white. 
 
 The rapper poured out his heart to the singer in an extremely revealing letter he wrote in jail. 
 
 Tupac writes, "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." 
 
 The legend then confesses, "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." 
 
 It's an amazing letter. Tupac clearly knows he devastated Madonna by the rejection, saying, "I never meant to hurt you." 
 
 You gotta read the entire note. It will go up for auction July 19-28 at Gotta Have Rock and Roll. Starting bid is $100k and it's expected to fetch a lot more. The last letter written by Tupac sold for more than $170k.
– Late rapper Tupac Shakur apparently had plenty of time to reflect while in jail in early 1995: He wrote a letter to ex-girlfriend Madonna explaining the reasons for their breakup, which he said happened partly because she was white, TMZ reports. "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 writes in the letter, which can be seen here. "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." Madonna didn't reveal until 2015 that she used to date Tupac, who was killed in a drive-by shooting in Las Vegas in 1996, Mashable reports. In the letter, Tupac tells Madonna he never meant to hurt her, saying, "I must apologize to you because like you said I haven't been the kind of friend I know I am capable of being." He says he has "grown both spiritually and mentally" since their relationship. He also tells her he was hurt by an interview in which she said, "I'm off to rehabilitate all the rappers and basketball players." Auction site GottaHaveRockandRoll.com plans to auction the letter off later this month, with $100,000 as the starting bid. (Another Tupac letter from jail sold for more than $170,000 two years ago.)