The Only Recap Of Leonardo DiCaprio's Downfall You Need

For three decades, Leonardo DiCaprio seemed untouchable, the idea of his downfall some sarcastically improbable punchline. With his boyish visage emblazoned upon a plethora of posters hugging the walls of international bedrooms and dorm rooms, the actor was Jay Gatsby for millennials and Romeo for Gen X. DiCaprio first burst onto the cultural zeitgeist at the age of 19 courtesy of the 1993 movies “This Boy’s Life” (opposite longtime collaborator Robert De Niro) and “What’s Eating Gilbert Grape” (opposite Johnny Depp). He earned Oscar and Golden Globe nominations for the latter, quickly becoming Hollywood’s “it” boy of the ’90s thanks to “Romeo + Juliet,” “The Basketball Diaries,” and “Titanic.”

In a move to transcend his youthful sex symbol status, DiCaprio gravitated toward darker roles and acclaimed directors, such as Steven Spielberg, Christopher Nolan, Quentin Tarantino, and Ridley Scott. It was his collaborative relationship with filmmaker Martin Scorsese, though, that would dominate DiCaprio’s career as a leading man, beginning with 2002’s “Gangs of New York” and extending across seven films since. In the midst of it all, he won the Academy Award for Best Actor thanks to his grueling physical performance in the 2015 film, “The Revenant.” Once deemed the “Prince of the City” by New York Magazine, DiCaprio had become “king of the world.”

Things look a lot different for DiCaprio 10 years after that Oscar win. He’s only appeared in three films over the past decade, with arguably more attention paid to his personal life than his work.

The cultural landscape had a much different topography in the 1990s than it does today, and arguably a much more sexist one at that. In these post-MeToo times, it’s practically impossible to imagine a popular actor getting away with leading a self-described “P***y Posse” as it charged its way through the world’s nightclubs like some irascible bull. However, that’s exactly what Leonardo DiCaprio did in the 1990s and part of the subsequent decade, alongside fellow posse members Tobey Maguire, Lukas Haas, Kevin Connolly, David Blaine, Harmony Korine, and others.

That ribald behavior was reflected in the underseen and semi-improvised film “Don’s Plum,” starring posse members DiCaprio, Maguire, and Connolly. Filmed in 1995 and 1996, before the actors’ most titanic successes, the black-and-white indie showcased the raw, nastier side of the group. It apparently revealed so much of their misogynistic “P***y Posse” behavior that both DiCaprio and Maguire have actively fought to prevent the film’s release. They’ve claimed that “Don’s Plum” was made as a favor to a friend and wasn’t intended to be released as a feature. After David Stutman, one of the film’s producers, alleged that they used their clout to block its distribution, the two actors ended up settling for $10 million in an agreement which allowed for a limited release outside North America. This is important because the film (and lawsuit) previewed the behavior that would lead to DiCaprio’s descent.

It’s one thing for Leonardo DiCaprio to party with the “Pussy Posse” in his 20s, but that dance of debauchery looks different when you’re 50. Part of DiCaprio’s downfall is due to the fact that he’s likely never shed his “Don’s Plum” days. Similarly, dating a 17-year-old when you’re 20 (as DiCaprio reportedly did with Bridget Hall in 1994) is more socially acceptable than dating a 19-year-old when you’re 48, as DiCaprio was rumored to have done with Eden Polani. Playing Romeo starts to wear thin at 50.

DiCaprio developed an unsavory reputation for dating models up to the age of 25, churning through Victoria’s Angels like a human checklist. DiCaprio’s age-gap relationships have been derisively referred to as Leo’s Law, and there was even a viral graph on Reddit that charts his dubious dating history. Women who dated DiCaprio before turning 25 include Bridget Hall, Kristen Zang, Amber Valletta, Bijou Phillips, Gisele Bundchen, Anne Vyalitsyna, Blake Lively, Erin Heatherton, Toni Garrn, and Victoria Lamas. DiCaprio’s relationships with Bar Refaeli, Nina Agdal, and Camila Morrone ended shortly after they turned 25.

To paraphrase a line from Matthew McConaughey’s character in the film “Dazed and Confused,” Leo gets older, they stay the same age. Granted, Leo’s Law has exceptions to prove the rule, namely his relationship with 27-year-old Vittoria Ceretti. Nonetheless, DiCaprio continues to be ridiculed for what’s considered his creepy tendencies.

Leonardo DiCaprio’s playboy history is only one element of a seemingly extravagant lifestyle that has come under scrutiny over the past decade, with the 50-year-old still partying like it’s 1999. Perhaps it’s merely a matter of envy, but the actor’s exorbitant, jet-setting ways have been criticized as not just a prolonged mid-life crisis but blatant hypocrisy, considering DiCaprio’s lifelong environmental advocacy and climate change activism. The actor has been a notable voice in that movement, sometimes quite literally, having narrated and co-produced multiple documentaries about climate change. DiCaprio’s passion for environmental causes has only motivated his critics further, who claim the actor hardly practices what he preaches.

DiCaprio’s frequent use of private jets — which pollute up to 14 times more than commercial airlines, according to TIME – initially came under fire in 2016 (arguably “Year One” of DiCaprio’s downfall). That’s when DiCaprio took a private jet from Cannes to New York in order to receive an environmental award from clean-water advocate Riverkeeper. He flew back to Cannes within 24 hours, and the next day took another private jet to travel less than eight miles, attending a gala in Antibes.

As if that wasn’t enough, DiCaprio parties year-round on environmentally ruinous superyachts and was once criticized for literally taking a helicopter from his yacht to dine and wine at a restaurant, according to The Toronto Sun. Leo loves ladies and liquor, after all.

Despite his apparent hypocrisy and the damaging signals it sends, Leonardo DiCaprio has nonetheless raised a lot of money for environmental causes — or has he? The Leonardo DiCaprio Foundation (LDF) was set up in 1998 for a variety of conservation efforts, but was relatively small until joining the California Community Foundation as a donor-advised fund (DAF) in 2008. Becoming a DAF has allowed the foundation to avoid transparency, making it practically impossible to glean its actual finances. According to the IRS, donor-advised funds can be used for “questionable charitable deductions” and “impermissible economic benefits to donors.”

All this has gotten the LDF and DiCaprio himself in hot water with the government. In 2016, the LDF raked in a whopping $45 million in donations during just one gala on July 20, where DiCaprio mingled with oligarchs such as Mohammed Al Turki and Dmitry Rybolovlev, and A-listers like Bono, Robert De Niro, Scarlett Johansson, and Arnold Schwarzenegger. That same day, the Department of Justice filed a complaint investigating a massive embezzlement case which involved the LDF and DiCaprio, who was named as “Hollywood Actor 1,” but not charged.

The DOJ alleges that DiCaprio’s foundation was used to embezzle millions of dollars from a Malaysian sovereign wealth fund actually intended for oil exploration, all as part of “the largest kleptocracy scheme to date,” according to the FBI. And DiCaprio was tight with the man behind it all — Jho Low.

Leonardo DiCaprio and his foundation both benefited greatly from a mysterious man named Low Taek Jho (aka Jho Low), the supposed mastermind behind the 1MDB scandal, which refers to the billion-dollar Malaysian sovereign wealth fund. A hard-partying big spender, Low would’ve fit right into DiCaprio’s “Pussy Posse,” but instead of traditional handsomeness and Hollywood success, Low had money, and lots of it. “Billion Dollar Whale,” a book about the current fugitive from justice, alleges that Low spent $85 million on parties between October 2009 and June 2010 alone. Siphoning hundreds of millions of dollars from the Malaysian state, Low paid DiCaprio a $250,000 fee to join him, according to ongoing federal investigations.

Beginning in November 2009, DiCaprio was paid to party internationally with Low, including an $11 million “gambling bender” in Vegas, according to The Hollywood Reporter. Low and his associates supposedly gifted DiCaprio a $9.2 million Basquiat painting, a $3.2 million Picasso, and Marlon Brando’s Academy Award for “On the Waterfront,” which was purchased for $600 thousand (via Artnet); DiCaprio had to surrender these items to the government.

Perhaps the weirdest part of DiCaprio’s relationship with Low is the fact that the latter provided financial backing for the former to portray an infamous financial criminal. Irony of ironies, Low contributed millions of (likely embezzled) dollars to help finance “The Wolf of Wall Street.” Yet, it’s doubtful that DiCaprio can surrender to the government the acclaim he received for that film.

While Jho Low may be the most notorious among them, Leonardo DiCaprio has gotten shady by proxy thanks to relationships that have contributed to the deterioration of his reputation. Several of these scandalized collaborators were involved in Red Granite Pictures, which helped produce “The Wolf of Wall Street” and later paid $60 million to settle an investigation into its involvement with Low and the 1MDB scandal. They include producers Joey McFarland, who had to forfeit $14 million in profits and gifts to the government, and Riza Aziz, who had to forfeit $107 million. Both men received a shoutout from DiCaprio during his Golden Globes acceptance speech in 2014, saying, “Joey, Riz and Jho, thank you for not only being collaborators, but for taking a risk on this movie.”

The whole 1MDB scandal even brought DiCaprio to the courtroom, where he was ordered to testify in a federal trial involving Low, embezzlement, and Prakazrel “Pras” Michel, a founding member of The Fugees. Michel, who often partied with DiCaprio and Low, was convicted on 10 counts regarding the funneling of money from the Malaysian government’s sovereign account. DiCaprio testified that he’d first met Michel backstage at a concert in the late ’90s, and said of Low, “I was given the green light by my team as well as my studio,” according to The Guardian. “He was a legitimate business person wanting to invest in the movie.”

Dana Giacchetto was an even shadier figure in Leonardo DiCaprio’s posse. Dubbed “the stockbroker to the stars,” Giacchetto dealt with myriad major megastars and their millions. “Leo DiCaprio is like my little brother,” Giacchetto told The Hollywood Reporter in April 2014, despite being sentenced to 57 months in prison for fraud in 2000 and reportedly losing money for clients, including DiCaprio. Before that, though, DiCaprio was deep with Giacchetto, even living in his SoHo loft in the late ’90s. DiCaprio skipped the 1998 Oscars (which “Titanic” swept) to instead party with Giacchetto.

Giacchetto was a member of DiCaprio’s “P***y Posse,” which adapted to more politically correct times by rebranding as the “Wolf Pack.” Members even had an actual necklace replete with a howling wolf pendant. Art dealer Helly Nahmad was another member, and yet another shady buddy who ended up in prison.

A close friend of DiCaprio’s, Nahmad was accused of being part of a multi-million-dollar money laundering scheme involving high-stakes poker games attended by DiCaprio and others. His 2014 plea deal led to Nahmad paying more than $6.4 million and receiving three years of probation after his prison sentence. However, Nahmad was later pardoned by Donald Trump at the end of his first administration; Nahmad also happens to own the 51st floor of Trump Tower in New York. Nonetheless, DiCaprio continued to party with his friend, boarding a private jet with him in 2023 (via the Daily Mail).

As if Leonardo DiCaprio’s relationships with shady friends (and some downright criminals) weren’t enough, the actor’s public reputation would suffer a further severe blow after his name was dragged into the Sean “Diddy” Combs controversy. While the media was focusing on the fallen rap star’s sex trafficking and racketeering trial, older photographs resurfaced, which revealed DiCaprio laughing and smoking with Diddy during one of his so-called “White Parties,” held annually from 1998 to 2009.

People also pointed to a 2017 Vogue video interview where Diddy claimed that he would revive the White Parties. The reporter asks, “Who’s the person that’s number one on that invitation list?” Diddy replies with just one name – “Leonardo DiCaprio.” The actor’s name also came up in text messages that were part of the court proceedings, according to Fox News, being mentioned by Diddy’s ex-assistant regarding a high-stakes poker game. “Leo [DiCaprio] grabbed my pink bedazzled BlackBerry, and you said, ‘That Titanic mother f***er doesn’t know s***. He won 10K, I won 650K.'”

Diddy’s White Parties and poker games do not implicate DiCaprio in any way regarding the “freak-offs” and criminal allegations. Nonetheless, DiCaprio’s bruised reputation and public downfall have made it easy for denizens of the internet to speculate about the extent of DiCaprio’s connections. “Makes sense considering the age group he prefers,” wrote one X user at the time, echoing the sentiments of many social media users (via FandomWire).

Alan Thicke, Leonardo DiCaprio’s one-time co-star in “Growing Pains,” told The Washington Post in 2015, “Leo is one of those guys everyone rooted for … just about anyone would tell you they enjoy celebrating by proxy.” Well, that was just before the aforementioned “Year One” of DiCaprio’s downfall, and today, even a seemingly innocuous image of the actor enjoying a Wimbledon tennis game brings out online haters.

On July 11, 2025, the Wimbledon X (formerly Twitter) account posted an image of DiCaprio, Rolex on wrist, sitting in the bleachers during a tennis match, captioning the photograph by writing, “Leonardo DiCaprio enjoying a Titanic tussle at SW19.” That’s all, no more, no less. Regardless, the comment section included a variety of negative criticism about the actor, from jokes about his dating life to his perceived environmental hypocrisy. “Fake environmentalist who loves his big private jets and yacht parties,” commented one user. “Leo attending Wimbledon to witness Novak’s #25 and then he will stop watching tennis,” wrote another. “Did climate pillock use a private jet or a diesel powered yacht to get there?” asked a critic.

While there were certainly some neutral or even positive comments, the fact that a completely innocent and arbitrary image of DiCaprio garners so much hate these days some see this as clear evidence of the actor’s public downfall.  Some tweets summarizing the overall sentiment of the comment section: “Top Diddy Client,” “Where’s his buddy Jho Low?” and “Ewww creep.”

These days, Leonardo DiCaprio seems to recognize the contempt with which the public perceives him. That’s probably why he attempts to obfuscate his appearance when he’s out and about, especially when he’s engaging in his most critiqued behavior, typically wearing a mask and a dark baseball cap that’s pushed further down than Chuck Schumer’s glasses. For instance, the noted environmentalist was berated for attending the lavish wedding of Lauren Sanchez and Jeff Bezos. Despite actively trying to avoid recognition, practically wearing his hat on top of his face, DiCaprio was nonetheless lambasted for his decision.

DiCaprio was one of many celebrity guests at the three-day wedding, which reportedly cost around $20 million. That’s barely a fraction of a percentage of what Bezos had made from founding Amazon, one of the world’s biggest polluters, with its production of 16.2 million metric tons of carbon dioxide each year. This is specifically why DiCaprio was criticized for his attendance, considering how vocal he has been about climate change advocacy. “I’ve had two great passions in my life. That has been acting, and the protection of the natural world and getting the message out about the climate crisis,” DiCaprio told Deadline in 2022. “I think there’s a worldwide sense of anxiety about the fact that the powers that be, the private sector, governments, are not making the transition fast enough.” Apparently, DiCaprio exempts Bezos from “the powers that be.”

Perhaps less focus would be placed on Leonardo DiCaprio’s personal life and connections if he actually starred in more movies. At the time of writing, he has only appeared in three films over the past decade, beginning with ‘Year One’ of the actor’s downfall. He received varying amounts of acclaim for these pictures (“Once Upon a Time in Hollywood,” “Don’t Look Up,” and “Killers of the Flower Moon”), which generally distract DiCaprio’s disdainful detractors when they are released. Even those who dislike DiCaprio’s performances often have to admit that he stars in high-quality movies.

Even though he’s making fewer films than ever, and despite his ongoing public downfall, DiCaprio is still demanding unrealistic amounts of money for them, usually between $20 and $30 million for lead performances. The actor has been in pay disputes over his small appearance in the proposed sequel to “Once Upon a Time in Hollywood,” turning down $3 million for just one day of filming. Maybe that’s one of the reasons why some other celebrities can’t stand him.

It remains to be seen whether DiCaprio’s newest film, “One Battle After Another,” will sway public discourse in any way. Considering the practically audible groans whenever DiCaprio is mentioned these days, it may be fair to say his downfall is permanent. Then again, there’s always time to grow up, even in your 50s.