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. ||||| Madonna has lost a legal battle to prevent the auction of personal items including a lock of her hair, her underwear and a breakup letter from former boyfriend, the late rapper Tupac Shakur. 
 
 The singer won a temporary block of the auction of 22 pieces in July 2016, telling a New York City court that her celebrity status “does not obviate my right to maintain my privacy, including with regard to highly personal items�?. 
 
 In a decision made public yesterday, judge Gerald Lebovits ruled that she had misdirected her legal action by targeting Darlene Lutz, the New York art collector who helped Madonna build a collection before the pair fell out. 
 
 Lebovits sided with Lutz, who claimed that the pair’s disputes had been settled in a 2004 legal agreement. The judge questioned why Madonna had pursued Ms Lutz rather than her own assistants, who Madonna claimed gave her possessions to the dealer. Lutz’s lawyer, Judd Grossman, called the decision “a total win�?, saying: “Ms Lutz is now free to do with her property as she pleases without any continued interference by Madonna.�? 
 
 Madonna is yet to comment on the ruling. 
 
 Facebook Twitter Pinterest ‘I never meant to hurt you’ ... Madonna and Tupac in March 1994. Photograph: Patrick McMullan/Getty 
 
 Auction house Gotta Have Rock and Roll has said it would continue with the sale of the items in July. In a statement, the organisation said it had been confident about the case and undertaken “substantial due diligence�? before announcing the initial auction. 
 
 Madonna and Tupac began dating in 1994. In the handwritten letter included in the auction, obtained by TMZ and dated 15 January 1995, the rapper says that his image would suffer from him dating a white woman. He expressed his discomfort with an interview in which the musician said: “I’m off to rehabilitate all the rappers and basketball players.�? 
 
 Madonna and Grimes lay bare cost of creative freedom for female artists Read more 
 
 “Can u understand that?�? he wrote. “For you to be seen with a black man wouldn’t in any way jeopardise your career. If anything it would make you seem that much more open & 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 rapper died in 1996, aged 25, in a drive-by shooting in Las Vegas. 
 
 The auction contains a second letter, sent from Madonna to “J�?, in which she describes Whitney Houston and Sharon Stone as “horribly mediocre�?. ||||| 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.)