The Breakup Letter That Madonna Received from Tupac Goes on Auction

Following a canceled auction from 2017, memorabilia company Gotta Have Rock & Roll has finally gotten the green light to auction the infamous letter Tupac Shakur wrote to Madonna from jail in 1995. In the handwritten document, Shakur explains he dumped the singer because of race and age issues.

A friendly break-up letter from late rapper Tupac Shakur to the Queen of Pop, Madonna, is set to be auctioned on July 17.

Given the hype and controversy surrounding the item, the starting bid will be set at $100,000 and is expected to be sold for over $300,000.

Madonna attends Edward Enninful's OBE dinner at Mark's Club on October 27, 2016. | Photo: GettyImages

Madonna attends Edward Enninful's OBE dinner at Mark's Club on October 27, 2016. | Photo: GettyImages

FAILED ATTEMPT TO STOP THE AUCTION

The company obtained the letter from Darlene Lutz, Madonna’s former friend, and art consultant, in 2017.

However, the singer filed an emergency court order to pull the breaks on the auction of the letter and other personal items owned by Lutz, including some panties, a brush with her hair and letters to and from different famous friends.

Madonna during a press conference for the Bridgestone Super Bowl XLVI halftime show at the Super Bowl XLVI Media Center on February 2, 2012. | Photo: GettyImages

Madonna during a press conference for the Bridgestone Super Bowl XLVI halftime show at the Super Bowl XLVI Media Center on February 2, 2012. | Photo: GettyImages

A New York Supreme Court ruling rejected Madonna’s request after learning she signed a “very broad” release in 2004 that made Lutz the legal owner of the letter so that she can sell it and the singer is in no position to sue Lutz.

THE LETTER’S CONTENT

The letter is three pages long and was handwritten by Shakur from jail in 1995. He was 24 at the time and was in a relationship with Madonna, who was 37.

Tupac Shakur backstage at the MTV Video Music Awards September 4, 1996 in New York City. | Photo: GettyImages

Tupac Shakur backstage at the MTV Video Music Awards September 4, 1996 in New York City. | Photo: GettyImages

Tupac explained to Madonna that he was ending their relationship because of the effects of dating an older white woman could have on his career.

“I must apologize to you," he wrote. "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 worthy, but at the risk of sounding overdramatic, the effects of racism make it difficult for a young black man to properly show affection for an older white woman. Can you understand that?”

And continues:

“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."

Excerpt from Tupac's letter on Gotta Have Rock and Roll's page. | Source: gottahaverockandroll.com

Excerpt from Tupac's letter on Gotta Have Rock and Roll's page. | Source: gottahaverockandroll.com

“NEVER MEANT TO HURT YOU”

He also added that he never meant to hurt the “Like a Virgin” singer, but he was so caught on her that he got scared he would be just another “toy.”

Tupac also mentioned an interview he read where Madonna allegedly said she was off to “rehabilitate all the rappers and baseball players,” adding that “those words cut me deep seeing how I had never known you to be with any rappers besides myself.”

 Tupac Shakur attends KMEL Summer Jam at Shoreline Amphitheatre on August 1, 1992. | Photo: GettyImages

Tupac Shakur attends KMEL Summer Jam at Shoreline Amphitheatre on August 1, 1992. | Photo: GettyImages

Shakur offered his friendship to Madonna, asking her to understand his previous position “as that of a young man with limited experience with an extremely famous sex symbol.”

He also advised the singer to be careful with people, as “there are those whose hearts bleed with envy & evil. They would not hesitate to do you harm!”

Excerpt from Tupac's letter on Gotta Have Rock and Roll's page. | Source: gottahaverockandroll.com

Excerpt from Tupac's letter on Gotta Have Rock and Roll's page. | Source: gottahaverockandroll.com

Tupac served nine months at the Clinton Correctional Facility in New York after being convicted on sexual assault charges. One year after being released from jail, he was murdered in a drive-by shooting in Las Vegas.

You can read the full letter here.

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