Madonna said in court documents that she was not aware until reading press reports that many of the items listed for auction, including the letter from her former boyfriend Shakur, were no longer in her possession, Reuters reported. Madonna’s representatives did not immediately respond to a request for comment. The items were originally up for bid last year, but the singer filed a temporary restraining order against New York auction house Gotta Have Rock and Roll to halt the sale, according to Reuters. “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,” Shakur 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.” 
 
 A second letter in the lot was an unsent draft written by Madonna to another former boyfriend, the actor John Enos. In it Madonna described two of her rivals, Whitney Houston and Sharon Stone, as “horribly mediocre,” adding, “They’re always being held up as paragons of virtue and some sort of measuring stick to humiliate me.” 
 
 Ms. Lutz said she came into possession of the items while frequently hanging around during that time in Madonna’s orbit, where she “tended to be a repository for a lot of stuff where people just thought: ‘Get rid of it.’” That included large piles fan mail that were often not examined at all, Ms. Lutz said.
– Bad news for Madonna: A judge on Monday said a New York auction house can go ahead and sell some of her personal stuff. Gotta Have Rock and Roll auctions got a hold of a pair of the singer's underwear, a letter Tupac Shakur wrote to her explaining why they had to break up, and other items of hers including a hairbrush, a checkbook, cassette tapes of unreleased recordings, a letter she wrote calling Whitney Houston and Sharon Stone "horribly mediocre," and photos. Madonna had obtained a temporary restraining order last year to halt the sale, saying she didn't know the items were no longer in her possession and believes someone took them from her home. But on Monday, a Manhattan judge ruled that the items belong to the auction house and the sale can go ahead, NBC News reports. The auction house says the sale will proceed in July. The Guardian and the New York Times explain that the judge found Madonna had targeted the wrong person in her legal action: Darlene Lutz, an art collector who helped Madonna build her collection before the two had a falling-out. Madonna claimed her assistants had given her things to Lutz, and the judge said Madonna should have targeted those assistants rather than Lutz. (Lutz herself once said that's how she came into the items, simply by collecting things that were otherwise going to be thrown out: "I knew all of the assistants and stuff would get thrown in boxes and they would just go, 'Hey, here’s some more.'") Lutz said she and the Material Girl had settled their disagreements in a 2004 legal agreement, and the judge sided with Lutz and found that that agreement prevented Madonna from suing. The judge also found that the statute of limitations to recover the items had passed. "Ms. Lutz is now free to do with her property as she pleases without any continued interference by Madonna," said Lutz's lawyer.