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‘Please Be Careful’: Legendary Rapper, Tupac Shakur’s Letter to Madonna Goes to Auction (Photo)

A letter written by famed 1990s rapper Tupac Shakur to pop idol Madonna during his nine-month stint in the slammer is set to go to auction on July 17.
On sale by auctioneer Gotta Have Rock and Roll, the once private letter is now going to the auction block with a starting minimum bid of $100,000. However, the company estimates that the handwritten missive will go for anywhere between $200,000 and $300,000.
In the infamous letter, which has been widely shared on social media for quite some time now, Shakur discusses the pair’s partnership, noting how race, societal norms and their celebrity status all played roles in the brief relationship.

“I’ve waited a long time 2 finally write this. Mainly because I was struggling to find all the answers so that I wouldn’t leave any unanswered questions,” Shakur wrote in his January 15, 1995, letter. 

“First and foremost, I must apologize to you because like you said I haven’t been the kind of friend I know I am capable of being. Not because I am evil or because you weren’t worth, but at the risk of sounding overdramatic, the effects of racism make it difficult for a young Black male to properly show affection for an older white woman. Can you understand that?”

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

In another section, the “Brenda’s Got a Baby” rapper goes on to ask Madonna to “remember me not for my shortcomings, but for the good times and the magic that we shared.”

“Now my outlook is different; Everyone is judged and treated not by their color or fame, but on how they treat me and because you have been so kind even in the midst of my craziness, I offer my friendship once again this time much stronger & focused.”

The three-page letter continues with Shakur urging Madonna to be careful and requesting that she visit him. He also explains in the letter that he felt compelled to write to the “Material Girl” singer “just in case anything happened 2 me.”

“Please be careful Madonna. Everyone is not as honorable as they seem. There are those whose hearts bleed with envy & evil. They would not hesitate to do you harm! Let my 5 bullets be proof of that!” he wrote, referencing the 1994 incident in which he was robbed and shot five times in a New York City recording studio.

Madonna has previously tried to stop the sale of the treasured letter, filing an emergency court order in 2017 in which she wrote that she wasn’t aware that the letter, in addition to various other personal items, was no longer in her possession. At the time, the letter and other items were in the possession of Darlene Lutz, Madonna’s former personal assistant.

In 2018, a judge ultimately ruled against the pop singer, and earlier this year the ruling was upheld by the Appellate Division of the New York Supreme Court, Rolling Stone reported.

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