Madonna’s love letter from Tupac is set to go under the hammer next week - and is expected to fetch up to £239k ($300k).
The 60-year-old singer lost a lengthy legal battle against her former friend, art consultant Darlene Lutz, to prevent her from putting the letter up for auction.
The three page handwritten note - sent by the late rapper from prison and dated January 1995 - reveals he broke up with Madonna because she was white.
Online auction site GottaHaveRockAndRoll.com is selling the note on behalf of Lutz with bids opening on Wednesday July 17 at £80k (£100k). A portion of the proceeds are being donated to breastcancer.org.
Madonna and Tupac dated briefly in 1994. The hip hop star was shot dead aged 25 in Las Vegas in 1996.
Madonna has tried to block the sale of the break-up note along with other personal items - including a hairbrush, photos and even a pair of panties she had once worn - consigned to Lutz, but she has lost in both the New York Supreme Court, and court of appeals.
Shakur opens the letter by apologising to Madonna, writing: “I haven't been the kind of friend I know I'm capable of being'.
“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,' he wrote later in the letter.
'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 went on: “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.
“I offer my friendship once again, this time much stronger and focused. If you are still interested would like to further discuss this with you, but some of it couldn't wait.'
“I felt compelled to tell you… just in case anything happened to me.” He died under two years later.
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Madonna claimed Lutz had, “betrayed my trust in an outrageous effort to obtain my possessions without my knowledge or consent.
“The fact that I have attained celebrity status as a result of success in my career does not obviate my right to maintain my privacy.”
But a judge ruled that Madonna had forfeited her right to the items after signing a 2004 settlement agreement with Lutz following a nasty dispute.