The relationship between the late hip-hop legend and pop icon Madonna has always been shrouded in secrecy and speculation. In 2015, while appearing on Howard Stern’s SiriusXM radio show, the Like A Virgin singer admitted that she secretly dated Tupac in 1994.
Now, a handwritten letter obtained by TMZ, and penned by a 24-year-old incarcerated Tupac, provides even further insight into the famous romance.
In the letter, which goes up for auction July 19 – 28 at Gotta Have Rock and Roll, Tupac writes, “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,” he confesses. Tupac, whose mother Afeni Shakur was a member of the Black Panthers, was known for his politicized raps, often covering topics to do with race and culture.
The letter, dated January 15, 1995, was sent just a month before the California Love rapper began serving his prison sentence on sexual-assault charges at Clinton Correctional Facility. On April 4, 1995, while serving his sentence, he married his long-time, off-and-on-again girlfriend, Keisha Morris – the marriage was annulled just 10 months later.
Later in the letter, the All Eyez On Me star tells Madonna “I never meant to hurt you.” It’s clear that his time behind bars had changed his perspective on both his life and his relationships.
“As you can see I have grown both spiritually and mentally. It no longer matters how I’m perceived,” he continues. “Please understand my previous position as that of a young man with limited experience with a extremely famous sex symbol. I offer my friendship once again this time much stronger and focused.”
“I felt compelled to tell you… just in case anything happened to 2 me,” he admits, in a somewhat ominous message. On September 7, 1996, Tupac suffered a fatal gunshot in a drive-by shooting while in Las Vegas. He died six days later at the University Medical Center of Southern Nevada. The murder was never solved.