Pop icon Madonna has lost a lawsuit in which she attempted to reclaim a love letter written to her by the late Hip Hop legend Tupac Shakur.

Last summer, a former employee of the “Material World” girl attempted to sell the letter, but Madonna tried to block the sale. A judge threw out her case because the 59 year old singer signed a release, giving her former employee to auction off the letter and other memorabilia when the two women ended their business relationship in 2004.

A segment of the letter reads below:

“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.”