Madonna Can't Stop Auction House From Selling Lock of Her Hair, Underwear, Tupac Breakup Letter

Madonna‘s attempt to block the auction of a handful of personal items — including a breakup letter from rapper Tupac Shakur, a lock of her hair, a pair of her underwear and a slew of personal photographs — has come up short.

On Monday, a judge in New York City ruled that auction house Gotta Have Rock and Roll had the right to sell Madonna’s items, NBC News reported.

The 59-year-old singer had filed a temporary restraining order last summer when the auction was first announced, Reuters reported — claiming in court documents obtained by the outlet that she was not aware the items were missing from her personal collection.

At the time, she put the blame on former friend and art consultant Darlene Lutz, who consigned the auction. Madonna said in court documents that Lutz had “betrayed my trust in an outrageous effort to obtain my possessions without my knowledge or consent,” Reuters reported.

But according to The Guardian, Manhattan Supreme Court Judge Gerald Lebovits sided with Lutz, pointing to the fact that Madonna and Lutz had settled their disputes in a legal agreement.

“We did substantial due diligence when we took all the Madonna items for auction,” Ed Kosinski and Pete Siegel, co-owners of Gotta Have Rock and Roll, told NBC News. “We were confident that Madonna had no claim whatsoever, and the judge clearly agreed with us.”

Reps for Madonna could not be reached by PEOPLE for comment.

A total of 22 pieces are included in the collection. Aside from the aforementioned items, there’s also another letter in which Madonna spoke about Whitney Houston and Sharon Stone.

The Shakur letter is the big-ticket item, with bidding starting at $100,000.

Penned on Jan. 15, 1995 while Shakur was at the Clinton Correctional Facility, where he was serving time on sexual abuse charges, the letter has the rapper expressing his sorrow for their breakup and admitting race was a big factor.

“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.”

“I never meant to hurt you,” he added.

RELATED VIDEO: The Truth Behind Tupac Shakur’s 1996 Murder: ‘It Was Simple Retaliation,’ Reveals an LAPD Source

He also explained he was angry after an interview Madonna gave in which she allegedly said, “‘I’m off to rehabilitate all the rappers & basketball players.’ ”

“Those words cut me deep seeing how I had never known you to be with any rappers besides myself,” Shakur wrote. “It was at this moment out of hurt and a natural instinct to strike back and defend my heart and ego that I said a lot of things. …Can you feel me?”

• Want to keep up with the latest from PEOPLE? Sign up for our daily newsletter to get our best stories of the day delivered straight to your inbox.

“In the time since, as you can see, I have grown both spiritually and mentally,” Shakur continued. “It no longer matters how I’m perceived. Please understand my previous position as that of a young man with limited experience with an extremely famous sex symbol.”