The Real Reason Tupac Broke Up With Madonna

Madonna has managed to survive in the ever changing landscape of the music industry for so many years because she's never been afraid to evolve, and with every evolution there came a brand new sound, a brand new style and — more often than not — a brand new man. In terms of her romantic life, the Like A Virgin singer is best known for her high profile divorces from Hollywood star Sean Penn and British movie director Guy Ritchie, but the relationship that has captured the imagination the most is the secret one that she shared with Tupac Shakur.

Madonna dated the late rap star in the mid-90s, not long before he was fatally wounded in a Las Vegas drive-by shooting. Details of their whirlwind romance have been scarce over the years (it wasn't even confirmed as fact until the singer dropped it into conversation on The Howard Stern Show in 2015), but the emergence of a letter sent from Shakur's prison cell has shed new light on just how close the pair actually got — and why it all came crashing down. Read on to learn the real reason that the King of Rap dumped the Queen of Pop.

Rosie Perez hooked them up

According to actress Rosie Perez (Do The Right Thing, White Men Can't Jump), she is the one who arranged Shakur's very first date with Madonna, hooking them up after the pop icon approached her during the 1993 Soul Train Music Awards. The rapper took Perez to the event after her date stood her up, which apparently didn't go down well with many of the females in attendance that night. "There were two girls, who shall remain nameless, who wanted to beat me up," Perez revealed on The View (via The Hollywood Reporter). "And I was telling Tupac, 'Will you tell them I ain't sleeping with you? We're just friends!' And he goes, 'You can take 'em.'"

Madonna was not one of those women, however. Instead of being jealous of Perez for showing up on Shakur's arm, she instead politely asked if she would put in a good word for her. "Madonna comes over, she looks at me, she goes, 'Girl.' I go, 'I gotcha,”' Perez recalled. She happily let her date know that Madonna was interested in him, and she still takes pride in the fact that she convinced him to give it a shot. "He goes, 'Hook that up.' I hooked it up, and I was very happy about it."

They passed secret notes

In 2015, Shakur's stepbrother Mopreme sat down with VladTV to discuss his famous younger sibling's career, and before long the subject of his love life came up. After revealing that Jackson made the rap star take an HIV test before they performed a kissing scene for 1993's Poetic Justice, Mopreme (also a rapper) got into the Madonna fling, explaining that he was once entrusted with a secret note. He was on set with Tupac for most of his movies and would often accompany his kid brother to press events, so he was used to seeing famous faces, but it still came as a surprise when Madonna (the most famous pop star in the world at the time) waltzed up and sat down next to him during a promotional interview for 1994's Above The Rim.

"She gave me a note to give to him," he said. "I was just happy she was giving him a note!" Mopreme (real name Maurice Williams) admitted that he was tempted to take a sneak peak at the words Madonna had scribbled down, but he was surrounded by the rest of 'Pac's entourage at the time so sadly didn't get the chance. "Everybody was there," he said. "I went over and gave [the note] to him. He was about the business and then they linked up. I would take him to her house and s*** when we got back to L.A. Yeah... They were a thing for a minute."

He made her feel like a gangster

While rumors swirled at the time (and continued to do so for years afterwards), Madonna and Shakur somehow managed to keep their romance out of the media spotlight. It wasn't until Madonna sat down for an interview with Howard Stern in 2015 that their relationship was finally confirmed, much to the shock of the DJ. The rapper came up in conversation when Stern asked the singer about her past interactions with late night talk show host David Letterman, which have been a more than a little awkward on occasion.

Madge brought up one show in particular — the infamous one from 1994 in which she called Letterman a "sick f***" for being obsessed with her sex life and went on to drop the F-bomb a total of 14 times. "Well, one time I was mad at him, when I said the F-word a lot, but the rest of the time was good," she told Stern. "You know what? I was in a weird mood that day. I was dating Tupac Shakur at the time and the thing is he got me all riled up about life in general. So, when I went on the show I was feeling very gangster."

He didn't want to date a white girl

In 1995, Shakur was jailed for the sexual assault of Ayanna Jackson, a 19-year-old fan of his who claimed to have been subjected to a horrifying gang rape by the famous musician and his friends in a luxury suite at New York's Parker Meridien Hotel. The rapper cried on the stand as he protested his innocence to the court, but he was found guilty and sentenced to four and a half years in prison regardless. He didn't end up serving his full sentence, but he was behind bars long enough to mull over his relationship with Madonna.

In a fascinating hand-written letter to the songstress that was made public in 2017, Shakur admitted that he had decided to end their relationship because he couldn't bring himself to date a white woman. "Can u understand that?" he asked in the three-page letter (obtained by TMZ). "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 explained. "I never meant to hurt you."

He was the jealous type

Shakur showed the kind of emotion that rappers often claim to lack during his court sentencing, and his subsequent correspondence with Madonna further proved that he had a largely unseen sensitive side. In the three-page letter, the platinum-selling artist brought up a saucy interview that Madge had given, and he didn't like what she'd been saying about his peers. The singer joked that she was on a mission to "rehabilitate all the rappers and basketball players" out there (she also had a fling with NBA star Dennis Rodman around this time), which rubbed Shakur the wrong way and appeared to cause a rift between the two.

"Those words cut me deep seeing how I had never known you to be with any rappers beside 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." He didn't repeat what those things actually were in the letter, but it's clear that Madonna's perceived promiscuity was bothering him. As for not knowing about any other rappers in the picture, Shakur must have missed the headlines that Madonna and Vanilla Ice were making a few years previous, although there's a fair chance that he simply didn't class Ice (real name Robert Van Winkle) as a real rapper.

He regretted dumping her

Shakur also expressed remorse over his decision to bring things to an end with Madonna based on the color of her skin during his heartfelt letter. He claimed to have grown both "spiritually and mentally" in the time that he'd been behind bars, indicating that he'd had a change of heart over the race issue and didn't care about his reputation anymore. "It no longer matters how I'm perceived," he told the "Material Girl" singer. "Please understand my previous position as that of a young man with limited experience with an extremely famous sex symbol."

Shakur wouldn't be the last man to struggle with the task of taming Madonna, and he certainly wasn't the first. In fact, the first rapper she got with ended things for the very same reason, dumping her after she published an explicit book (complete with photographs) entitled Sex. "I was hurt to be an unwitting part of this slutty package," Vanilla Ice told News of the World, (via Digital Spy). "We were in a relationship, yet it looked like she was screwing all these other people. I thought she was taking pictures and running around naked because she was like that. Then when the book came out I was so embarrassed and ashamed. It was a porno."

Shakur wanted her to visit him in prison

The overall gist of Shakur's letter (the parts that have been made public, at least) was that he was sorry about the way he had broken up with Madonna and had learned a lesson from it, but he signed off by saying that he had a lot more to say to her if she was willing to hear it. The rapper indicated that he would have liked the pop star to visit him at the Clinton Correctional Facility, even if it was just as friends.

"Like you said, I haven't been the kind of friend I know I am capable of being," he wrote. "I offer my friendship once again, this time much stronger and focused. If you are still interested [I] would like to further discuss this with you, but some of it couldn't wait. I felt compelled to tell you... Just in case anything happened to me."

The gang-affiliated musician was clearly worried about the dangers of prison life, but as we know it turned out he wasn't safe on the outside, either. It also turned out that Madonna wasn't the only female he was writing while banged up. Shakur actually married a woman named Keisha Morris during his prison term, but it didn't last. They wed on April 4, 1995 but divorced in 1996, just months before his fatal shooting.  

But she never did

Despite his offer, Madonna chose not to visit Shakur in prison. At least, that's the official line. In truth, the singer has always flat out refused to either confirm or deny that she went to see the incarcerated rapper, and she dodges the question whenever she's asked it directly. When Shakur's letter to her surfaced, she was once again quizzed about whether or not she ever dropped in on the jailbird, and again she refused to engage on the matter. "I'm not answering that question," she is quoted as saying by The Sun. "It's not relevant to this letter."

Shakur himself denied that such a visit ever happened (though that could have had something to do with the fact that he was involved with Keisha Morris at the time), but he did say that he was glad the story made the news. "Madonna is real nice," he said. "She's a good person. She helped me a lot. She was real cool. Like any one of my homeboys. One time, they had a story on the local news out there that Madonna was coming to visit me. Madonna has so much power that the guards let me take an extra shower because they thought she was coming to visit me!"

Did she want his children?

It's hard to keep track of Madonna's kids sometimes, but the last time we did a head count she had six (two biological, four adopted). Daughter Lourdes Leon is the eldest of the lot, born in 1996 after her mother had a short relationship with her personal trainer Carlos Leon. She also gave birth to a son during her time with ex-husband Guy Ritchie, with Rocco Ritchie joining the party in 2000. In 2006 she adopted David, the first of four children from Malawi the singer would end up giving a new home to — Mercy followed in 2009, and twins Stella and Esther in 2017.

According to biographer Lucy O'Brien, things could have been quite different. In her book Madonna: Like an Icon (via New York Daily News), the author claims that the Queen of Pop "desperately wanted children" by the time she started seeing Shakur (she was in her mid-30s by then, while her rapper beau was still in his mid-20s). Sadly, a Pac/Madge love child never came to be, and we're left to simply imagine what kind of music said love child might have grown up to make.

The letter is being auctioned off

The reason Shakur's letter has been back in the news in 2018 is that Madonna has just lost her legal bid to stop it from being sold at auction. The singer's former BFF Darlene Lutz has put the intimate three-page letter up for sale along with a hairbrush that used to belong to the superstar and a pair of worn panties. Of course, the vast majority of people aren't going to have much interest in items two and three, but the handwritten letter from Shakur could well fetch a small fortune.

A judge in New York threw the singer's lawsuit against Lutz out in April 2018, telling her that the statute of limitation had passed and therefore there was nothing she could do to stop the sale. Madonna claimed that she didn't know Lutz was in possession of Shakur's letter until she read about the auction, but Lutz' lawyers denied this and accused the songstress of a "personal vendetta" against their client, the BBC reports.

The pair previously went through a bitter court battle over some artwork, which Madonna won. But, as part of the deal, she had to sign papers stating that "any and all" future claims against Lutz would be void, meaning her ex-friend is free to sell all the old pairs of undies she finds. Meanwhile, fans of both Madonna and Shakur are anxiously awaiting the sale of the letter, hoping that the buyer reveals it in its entirety. Watch this space.