It was one of the unlikeliest pairings of the 1990s: the son of a Black Panther and the biggest pop star in the world. How long Tupac and Madonna were together is unclear. How it ended is set down in a letter Tupac wrote from prison.
How it started
The relationship dates to 1994; Madonna confirmed it publicly in 2015, talking to radio host Howard Stern. Actress Rosie Perez told the story of how they met on The Wendy Williams Show in 2014: Tupac agreed to be her date at the Soul Train Awards, on the condition that she introduce him to Madonna. Asked whether that happened, Perez nodded.
It is often claimed that the two met while Tupac was filming Above the Rim in New York, that they went to a taping of Saturday Night Live together on April 2, 1994, and that Tupac told his bodyguard Frank Alexander about a few nice weeks with Madonna. None of these details could be verified.
The letter from prison
A letter Tupac wrote in jail to “M” is dated January 15, 1995, a few weeks before he was sentenced in his sexual abuse case. The BBC gives Clinton Correctional Facility in upstate New York as the place it was written. According to the Daily News, however, Tupac was still being held on Rikers Island in January 1995; he was only moved to Clinton after his sentencing in February. It is a rare document, because in it Tupac speaks openly about race and image. “For you to be seen with a black man wouldn’t in any way jeopardize your career,” he wrote; if anything, it would make her look more open. He, on the other hand, feared that because of his image he would be letting down half of the people who had made him what he was.
What hurt him, he wrote, was an interview in which Madonna said, more or less, that she was off to “rehabilitate all the rappers and basketball players.” Stung, he had said a lot of things in return. “I never meant to hurt you,” he wrote, asking her to see his earlier stance as that of a young man with limited experience dealing with an “extremely famous sex symbol.”
What Tupac said in public
In the interview he gave VIBE from prison in the spring of 1995, Tupac was blunter. “I was letting people dictate who should be my friends,” he said. Because he saw himself as a big Black Panther type, he thought he couldn’t be friends with Madonna, so he dissed her, “even though she showed me nothing but love.” When he went to jail, he said, she was “the only person that was willing to help me. Of that stature.”
The letter in court
In July 2017 the auction house Gotta Have Rock and Roll offered the letter with a starting bid of $100,000, alongside other personal items of Madonna’s that came from art dealer Darlene Lutz, a former confidante of the singer. According to the BBC, Rolling Stone confirmed the letter was authentic. In July 2017 Madonna won a temporary halt to the sale, citing her privacy.
In April 2018 she lost the case: Judge Gerald Lebovits in New York ruled for Lutz on narrow legal grounds, pointing to a 2004 agreement between the two women. A New York appeals court upheld the ruling in June 2019, and in July 2019 Gotta Have Rock and Roll put the letter up for auction again, once more with a starting bid of $100,000. Whether it was sold, and for how much, is not documented in the sources checked here.