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It’s surprising to think that an artist as provocative as Madonna would have any secrets. However, in 2017, the singer tried to stop an auctioneer from selling one of her personal effects. It was a letter from a past love, one that revealed secrets about them both. And it was a relationship that the star had long kept private.

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Several of Madonna’s personal belongings were set to go to auction in 2017. As a result, the singer fought back against the breach in privacy by asking a judge for an injunction. And it wasn’t just the letter up for grabs. Fans could also purchase several of her famous wardrobe items, including a pair of latex briefs she wore in L’uomo Vogue magazine.

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It was, however, the love letter that grabbed headlines at the time. Perhaps unsurprisingly, the auctioneer seemed to believe that its secret details would tempt wealthy bidders to spend more than $100,000 to get hold of the note. Madonna’s attempts to stop the auction, though, failed. As a result, the correspondence went up for sale in the summer of 2019, and it was then that the world learned of its juicy contents.

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Michigan native Madonna Louise Ciccone decided to leave college behind in 1978, foregoing her studies for the bright lights of New York City. She hopped on a plane and flew to the Big Apple, arriving with just $35 to her name. And like many others who flocked to the East Coast metropolis, she had big dreams.

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Once in New York, Madonna booked gigs as both a dancer and back-up singer, all leading up to her turn in the spotlight. That moment came in the early 1980s when Seymour Stein, founder of Sire Records, heard the music she’d been working on. Soon enough, she had a record deal and two top-ten dance-chart hits in the US – “Everybody,” and “Burning Up.”

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After that, Madonna skyrocketed to fame and has remained in the public eye ever since. She’s had a slew of hit songs, including “Like a Virgin,” “Vogue,” “Like a Prayer,” “Hung Up,” “Ray of Light” and “4 Minutes.” Over the course of her career, the singer has won seven Grammy awards, including the 1999 trophy for Best Pop Album, which went to her seventh album, Ray of Light.

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Madonna’s super-stardom, though, wasn’t the only thing keeping her in the headlines. The famous singer has long been the subject of tabloid fodder, thanks to her high-profile relationships. Indeed, the Grammy winner has been a celebrity for more than 30 years, and the press has followed her love life practically the entire time.

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The first of Madonna’s famous beaus was the singer Prince, whom she met at one of his gigs. Some say he broke off the mid-80s fling because she came on too strong. Others contend that she dumped the “Purple Rain” singer because he wanted a committed relationship and she didn’t. Either way, it seemed they walked away without hard feelings. The diminutive pop genius even featured on her 1989 album, Like a Prayer.

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Madonna’s next high-profile relationship became a lot more serious than her rendezvous with Prince. This time, she happened to meet actor Sean Penn while at a movie studio in 1984. At the time, she was making the video for her song, “Like A Virgin.” Within six months of that moment, the pair said, “I do.”

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Perhaps unsurprisingly, the whirlwind romance between Penn and Madonna didn’t stand the test of time. Their marriage lasted a mere four years before they called it quits. However, the former lovebirds remain friends. The singer even later admitted that, out of all of her romantic pairings, she still thinks the actor is the love of her life.

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Nevertheless, love found Madonna several more times after things ended with Penn. Her next serious relationship kicked off in 1994, a decade after she met her ex-husband at a Hollywood studio. This time, the “Like a Prayer” singer fell for a New York City-based personal trainer named Carlos Leon.

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Some say that Madonna and Leon secretly became engaged during their relationship, which lasted three years. They never tied the knot, but the couple did mark one very special milestone together – the singer and her trainer beau had a daughter named Lourdes in 1996. Also known as “Lola,” the little girl was the singer’s first child.

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Lourdes’ arrival inspired one of Madonna’s most critically acclaimed albums, Ray of Light. The relationship between the singer and Leon, however, fizzled shortly after they had their daughter. Still, the former couple successfully co-parented the little girl until she reached adulthood – and began to pursue a creative career, just like her mother.

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Two years after Madonna’s split from Leon, she fell into her next serious relationship. In 1999 fellow musician Sting introduced her to director Guy Ritchie, igniting a romance between them. Just before Christmas in 2000, the couple exchanged vows in Scotland, but their wedded bliss wouldn’t last.

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Ritchie, it seems, struggled with the outside world’s take on his relationship with the singer. Namely, he hated it when the press referred to him as “Mr. Madonna.” And, while much of the couple’s union took place in the spotlight, the director supposedly dreamed of a simpler husband-and-wife set-up than the one he had.

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Nevertheless, it was Madonna who pulled the plug on their marriage in October 2008. By then, the couple had welcomed two sons – Rocco John, and their adopted son, David, who they brought home from Malawi. After settling on a custody arrangement, the singer then forked over a record-breaking $80-million divorce settlement before parting ways with Ritchie.

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After Madonna’s marriage to Ritchie, the singer took a decidedly casual approach to her relationships. Case in point – her 12-month relationship with Jesus Luz, which began just after her divorce. At the time, he was 21 years old, a great deal younger than the then-50-year-old star.

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When Madonna’s relationship with Luz fizzled in 2010, she seemingly took a long hiatus from romance. It wasn’t until 2017 that she found herself in another long-term relationship. This time, the world-famous singer set her sights on Kevin Sampaio, a model who co-starred in her music video for the 2015 single, “B**** I’m Madonna.”

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In the video, Madonna and Sampaio lock lips on camera. And soon enough, life began to imitate the star’s art. The pair have been supposedly been together since 2017. And, during that time, the Grammy winner has been pleased with the model’s ability to keep their relationship details to himself and out of the tabloids.

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And yet, none of these beaus penned the love letter to Madonna that went up for auction in 2019. Instead, it was the man she met at the 1993 Soul Train Awards through actress Rosie Perez. In 2015 Perez recalled the story on The View, saying she had gotten stood up by her original date for the night.

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So, none other than rapper Tupac Shakur stepped in to accompany Perez to the award show. As the actor recalled it, all the women that saw Shakur were jealous of her handsome date – but one in particular made a move. She told The View, “Madonna comes over. She looks at me, she goes, ‘Girl.’”

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Then, Perez let Shakur in on Madonna’s interest in him. He had a simple response, as the actor remembered it. He said, “Hook that up.” And, from there, a fling between the rapper and the pop star began. The pair kept their relationship out of the public eye, although the “Material Girl” singer would eventually reveal in 2015 that it had happened.

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And, according to Madonna, that tryst with Shakur led to one of the most noteworthy interviews of her career. On March 31, 1994, she appeared on the Late Show With David Letterman. But the singer wouldn’t sit down for the typically humorous one-on-one with the show’s host.

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Instead, Madonna gave a famously R-rated interview. During the chat, she said the F-word a whopping 14 times, making it the most censored talk-show moment in history. More than 20 years later, she blamed the rapper for her behavior. She said in a 2015 interview with Howard Stern, “I was dating Tupac Shakur at the time and, the thing is, he got me all riled up on life in general. So when I went on the show, I was feeling very gangsta.”

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But all of that energy and excitement between Madonna and Shakur wouldn’t last. Instead, the pair broke up. After that, the rapper was sent to the Clinton Correctional Facility in New York state on a sexual assault charge that he vehemently denied. And while behind bars, the rapper seemed to get reflective about his relationship with the super-star.

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In 2017, the contents of Shakur’s letter became public, and they shocked everyone. In it, the rapper talked about why he had to break up with Madonna. But he began his message by explaining the reason for sending the note. He wrote, “I’ve waited a long time [to] finally write this, mainly because I was struggling to find all the answers so that I wouldn’t leave any unanswered questions.”

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Next, Shakur apologized to Madonna because, as he put it, “I haven’t been the kind of friend I know I am capable of being.” Then came the rapper’s explanation as to why he’d ended things with the Grammy winner. It all had to do with the public’s perception of them as a biracial couple.

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Shakur wrote, “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.”

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But that wasn’t all Shakur had to say to Madonna. He then aired a grievance regarding an interview she had given. In the letter, the “Changes” rapper recalled “an interview where [Madonna] said, ‘I’m off to rehabilitate all the rappers and basketball players,’ or something to that effect.”

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Needless to say, such a statement bothered Shakur. He wrote, “Those words cut me deep, seeing how I had never known you to be with any rappers before myself.” Apparently, Madonna’s interview drove the hip hop star to breaking point. The letter continued, “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.”

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But Shakur’s letter wasn’t only about rehashing the end of his relationship with Madonna. He, in fact, also shared with her how much he had changed since then. He wrote, “As you can see, I have grown both spiritually and mentally. It no longer matters how I’m perceived.” On top of that, the rapper blamed the break-up on his “limited experience with an extremely famous sex symbol.”

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In closing the letter, Shakur offered Madonna his “friendship once again, this time much stronger and focused.” And, in an eerie bit of foreshadowing, the rapper explained why he couldn’t express all of this in person to his ex-girlfriend. He wrote, “I felt compelled to tell you… Just in case anything happened to me.”

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On that note, Shakur concluded his letter with a warning to his former flame. The “California Love” rapper wrote, “Please be careful, Madonna. Everyone is not as honorable as they seem. There are those whose hearts bleed with envy and evil. They would not hesitate to do you harm! Let my five bullets be proof of that!”

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Shakur’s heartfelt letter signified that he was, indeed, ready to move on. Just months after sending that message to Madonna, he and Keisha Morris tied the knot in April 1995. The pair had met before the rapper landed in prison, and their nuptials took place while he was still behind bars. Upon his release from jail, though, the union crumbled.

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And nearly two years after Shakur penned that letter to Madonna, the advice he gave became chilling when he met an untimely end. On September 7, 1996, a car pulled up next to his, and someone inside sprayed bullets into the rapper’s vehicle. He sustained four gunshot wounds, and died six days later of internal bleeding.

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In the years following Shakur’s death, Madonna remained tight-lipped about their time together. Over 20 years later, however, the star finally confirmed, in 2015, that she had, indeed, dated the famous rapper. And two years after that disclosure, the songstress found herself in front of a judge to fight the sale of the very personal message he sent her in 1995.

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According to a 2019 piece in Rolling Stone magazine, Madonna tried to stop the sale of Shakur’s letter because her celebrity status “[did] not obviate [her] right to maintain [her] privacy.” Initially, the court agreed and issued an injunction against the sale. In 2019, however, an appeal in the case overturned that ruling. As a result, the world could read and bid on the rapper’s letter to her.

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The memorabilia site GottaHaveRockAndRoll.com put the letter up for bids in July 2019. They have re-sold everything from John Lennon’s necklace to Elvis Presley’s peacock jumpsuit. And yet, in the description of Shakur’s letter, the vendors wrote that the piece was “one of the most significant music artifacts to ever come to auction.”

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As such, GottaHaveRockAndRoll.com placed the minimum bid on the letter at $100,000, and estimated that it would go for two to three times that price. In the end, though, no one bought Shakur’s private letter to Madonna. That, perhaps, was a confirmation of the singer’s opinion that his handwritten message was a bit too private for the public to read.

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Since then, Madonna has switched gears to focus on her current music instead of her past relationships. In the summer of 2019, in fact, she released her 14th album, Madame X. Following that, the star embarked on an 85-stop world tour for the album, which will conclude in Paris in March 2020.

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