Two years ago, Madonna attempted to stop its sale when she told a judge that her celebrity “does not obviate my right to maintain my privacy.” An appeals court overturned that injunction last month. The letter is headed to the auction block on July 17th with bids starting at $100,000. Auctioneer Gotta Have Rock and Roll estimates it will go for between $200,000 to $300,000 even though scans of it have been floating around the Internet for years and you can even read it in full on its website.
The three-page letter, dated January 15th, 1995 — a year and change before he was fatally shot — he apologized to the singer for not being “the kind of friend I know I am capable of being.” The artists dated briefly in the Nineties, though they kept it secret; in 2015, Madonna said that Shakur had riled her up before a shocking 1994 appearance on David Letterman so she was “feeling very gangster” when she said the word “fuck” 13 times on air. But they kept their relationship secret. In the letter, Shakur wrote that he felt uncomfortable being seen with a white woman because he “would be letting down half of the people who made [him] what [he] thought [he] was,” whereas dating a black man would help her career. He wrote that he also took umbrage to her allegedly saying it was her job to “rehabilitate ll the rappers and basketball players.”
“Those words cut me deep seeing how I had never known you to be with any rappers besides myself,” he 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 I have since come to regret.” He followed that by writing that he had “grown spiritually and mentally” since then.
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Part of the reason he wrote the note was because he wanted to tell her how he felt “in case anything happened 2 me.” He added that “everyone is not as honorable as they seem … let my five bullets be proof of that.”
In July 2017, a judge stopped the sale of the letter and 21 other items after Madonna filed an emergency court order. Bidding on the letter had reached $100,000 by that point. In her filing, she wrote that she wasn’t aware that the letter and other potential auction items were out of her possession; much of the auction had been donated by her former personal assistant, Darlene Lutz. In April 2018, a judge ruled in favor of the auction house, saying that Madonna should have known Lutz was in possession of things like the letter and didn’t make any attempt to stop the auction before it had begun. That ruling was upheld the Appellate Division of the New York Supreme Court on June 4th of this year, according to the auction house.
Even though Shakur wrote the letter after the couple had broken up — he was serving nine months in prison for sexual assault at the time he wrote it — Gotta Have Rock and Roll is referring to it as a “breakup letter.” He married his longtime girlfriend, Kiesha Morris, on April 29th (two months before writing the letter to Madonna) but divorced her seven days after his release in October 1995.
Partial proceeds from the sale will go to BreastCancer.org.