Shady Rumors About Leonardo DiCaprio We Can't Ignore

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Leonardo DiCaprio's relationship history has given rise to some unsavory rumors about the actor's character. After taking a quick peek at the women the "Titanic" star has dated over the years, it's clear that he has a thing for models who are considerably younger than him. Upon closer inspection, people realized that the majority of the Oscar winner's partners have been in their early twenties. And, according to a New York Post insider, there's a reason why DiCaprio refuses to date women older than 25. 

"By the time girls reach 25, they're looking for more — they're looking to get married and settle down," the confidant claimed, per Page Six. "That is not what Leo wants. He does not want a family and does not want to be around women who may press him for that. The minute a girl meets him, the clock is ticking." They also stressed that the "Revenant" star wouldn't hesitate to call off a relationship if he believed a woman was crossing his age threshold or trying to establish a deeper connection with him. 

The insider's account made DiCaprio seem immature, and some of his exes may agree with that. In fact, Kristen Zhang, who dated the actor for about a year in the 1990s, apparently ended things with him for this very reason. In Gisele Bündchen's 2018 memoir "Lessons: My Path to a Meaningful Life," she alluded to how her 5-year relationship with the "Django Unchained" star ended because she wanted to mature and stop relying on unhealthy coping mechanisms, but he wanted to stay the same. There are plenty of other, similarly distasteful rumors that DiCaprio has been unable to escape too.

Over the years, Leonardo DiCaprio has championed environmental conservation through documentaries, impassioned speeches, and multi-million dollar donation pledges. But the actor's jet-setting habits have led people to question whether his activism is simply a means for DiCaprio to further his public image. According to the Daily Mail, the Oscar winner took 20 flights in 2014 alone. While some were attributed to work, others were just him travelling around the globe for fun. During Summer 2014, the former child star who lives an insanely lavish life also partied on an oil tycoon's yacht.

According to the tabloid's calculations, even if the "Great Gatsby" star had made the highly unlikely but eco-conscious decision of flying commercial for all his flights, DiCaprio's many journeys still would have added a massive 40 million metric tons of CO2 to the atmosphere. Ironically, in 2016, the beloved actor hopped on a private jet for an 8,000-mile flight from France to New York to accept an award for his climate change activism. According to Page Six, DiCaprio made a round-trip journey on a private jet from Miami to New York in one day to attend a fundraiser for COVID-19 too. 

Speaking to Fox News in 2016, environmental analyst Robert Rapier argued that the "Don't Look Up" star's  luxurious means of travel "[diminishes] his moral authority to lecture others on reducing their own carbon emissions." Moreover, he professed that DiCaprio's behavior represented why fossil fuel consumption is on the rise, since he's likely adopting the common mentality of "I've got a good reason for consuming what I consume."

According to a 2018 report in Page Six, Leonardo DiCaprio's annual charity auction for the Leonardo DiCaprio Foundation included some bizarre items. In 2016, they offered bidders the chance to have Kevin Spacey over and witness him in "a private theatre performance." Since 2017, several men have come forward to accuse Spacey of sexual assault, misconduct, and harassment. However, the "American Beauty" star notably wasn't the only controversial figure to nab a spot in DiCaprio's auction. In 2015 and 2016, attendees could also bid on spending a year with Harvey Weinstein, who has been publicly accused of sexual assault and harassment by numerous women since 2015 and in 2025 was found guilty of sexual assault in New York.

"The Courtesy of Harvey Weinstein Experience" offered one (un)lucky bidder the chance to walk the MET Gala red carpet with him and have a seat at the disgraced producer's table during his company's starry Oscars' Eve dinner party. They could also intern at The Weinstein Company and accompany Weinstein around a movie set. A rep for DiCaprio's charity responded to the report with a statement, asserting, "LDF never received payment for any auction lots donated by Mr. Weinstein or Mr. Spacey, which were included in our 2015 and 2016 catalogs." 

Meanwhile, in 2016, the Hollywood Reporter noted that DiCaprio's foundation was unusually tight-lipped about its basic inner workings. Many attendees of the Leonardo DiCaprio Foundation's galas claimed that the glitzy annual event was an over-the-top party where people had sex in the bathrooms. Gala-goers also noted that it was overpopulated with inebriated women rather than the wives of the men in attendance.

If you or anyone you know has been a victim of sexual assault, help is available. Visit the Rape, Abuse & Incest National Network website or contact RAINN's National Helpline at 1-800-656-HOPE (4673).

Leonardo DiCaprio and Tobey Maguire have a surprising friendship that goes back decades. Although Maguire and DiCaprio have done several movies together, they reportedly hoped one of them would never see the light of day: "Don's Plum." According to the New York Post, the movie's plot revolved around a male friend group who went to a Los Angeles diner called Don's Plum every Saturday night with the women they were dating that week. The movie featured primarily improvised dialogue, including a shocking scene of DiCaprio throwing a bottle at a woman after cautioning, "I'll f**king throw a bottle at your face, you goddamn w***e." 

One of the film's producers, Dale Wheatley, acknowledged that the "Inception" star wasn't onboard with the idea of veering away from the original plan of "Don's Plum" being a short because he was worried it would bomb as a feature-length and negatively affect his career. Meanwhile, in a Vanity Fair interview, Wheatley disclosed that the Oscar winner was also, unsurprisingly, concerned that the movie's misogynistic themes wouldn't sit well with his primarily female fanbase. 

Although "Don's Plum" ultimately got a feature-length cut, it was banned from release in North America and Canada due to the terms of a lawsuit settlement between DiCaprio's team and the film's producers. Notably, in a 1998 lawsuit from another producer, David Stutman, he alleged that both DiCaprio and Maguire had "carried out a fraudulent and coercive campaign to prevent release of the film." Additionally, Wheatley published a scathing open letter to the "Aviator" star on his website, slamming DiCaprio for "bullying, censorship, and abuse of power."

Leonardo DiCaprio's history of failed high-profile relationships and his tendency to jump from one model to another has earned the Oscar winner the reputation of a playboy who will never settle down. We learned that this actually began in the early days of his career, as DiCaprio's friend group was called "The P****y Posse" because of their desire to have sex with as many women as possible, per a 1998 New York Magazine profile. According to the report, the nineties icon and his pals also threw grapes at the paps from a hotel room. 

As a 2003 report in The Guardian pointed out, DiCaprio also pelted horse manure at the paparazzi when he was filming "Gangs Of New York" about a year prior. His co-star, Daniel Day-Lewis, and famed filmmaker Martin Scorsese were also reportedly fed up with his partying habits. At one point, things got so bad that Day-Lewis had to move to a different hotel from DiCaprio just to get some peace. In fact, even the writer of the New York Magazine article wasn't spared his bad boy behavior. 

She divulged that the then-24-year-old actor had left her a drunken voice message saying that he would agree to an interview only if she did something similar to what Monica Lewinsky did for Bill Clinton. In 2003, The Guardian reported that Elizabeth Berkley's ex-boyfriend, Roger Wilson, was suing the infamous friend group for beating him up on DiCaprio's orders. The "Beach" star was apparently hurt because Berkley had turned him down, an allegation DiCaprio's rep denied to the outlet. 

As Bloomberg reported in 2003, Leonardo DiCaprio was once close friends with Jho Low, a Malaysian businessman who became a fugitive after embezzling $4.4 billion from a state-owned company, 1Malaysia Development Berhad. The FBI discovered his tight bond with DiCaprio through thousands of messages the pair had shared over the years. Additionally, Low called the Oscar winner "Ldogg" and even their mothers had met. However, when DiCaprio was questioned about their relationship in front of a grand jury, he stated only that he "was working for him and that business also translates into being social. And so we saw each other more, and there was more interaction." 

Notably, Low donated a whopping $6 million to Leonardo DiCaprio Foundation, alongside showering him with expensive gifts such as Marlon Brando's Oscar for "On the Waterfront" and a first edition of "The Great Gatsby." Both presents were ultimately handed over to the FBI. According to The Hollywood Reporter, Low was the contact point between Riza Aziz and Joey McFarland, who were the founders of Red Granite Pictures, a company that produced "The Wolf of Wall Street." 

The DOJ later alleged that the production house's contributions came in part from Low's embezzled funds. In Bloomberg's report, there was also an eyebrow-raising text between DiCaprio and his manager, Rick Yorn, from December 2013, in which the latter wrote, "Need to talk about what I think is the 'cracking of the code' structure/deal for you." Although it's unclear what he was referring to, the actor later confirmed that he had clued Low in on his plans, and he was in.