Enter the gates of Mar-a-Lago and you never know who you might run into. Guests at the sprawling Palm Beach estate aka the winter White House might brush past a foreign dignitary, a hopped-up tech titan, a mysterious Chinese billionaire or an overly Botoxed reality star.

So when Casey Wasserman arrived for a private meeting in January, just days before Donald Trump was sworn in for a second term, he was prepared for anything. As one of the Democratic Partys most loyal donors and a close friend of former House Speaker Nancy Pelosi the 51-year-old sports impresario could reasonably expect a frosty reception from a president-elect whod promised revenge on his political foes. Instead, after a short wait alongside his girlfriend, Jenny Chandler, the conference room doors swung open. Trump and first lady Melania swept in trailed by a surprise third party.

And then in walks Brett, Wasserman tells The Hollywood Reporter.

Brett Ratner, the Hollywood director exiled during the height of #MeToo, was filming a $40 million Melania Trump documentary for Amazon. Wasserman hadnt seen him in years. I dont know if Im in the documentary, he says. They only filmed the moment he walked in and when we shook hands.

At any other time in U.S. history, the sight of the president and first lady followed by a canceled Hollywood director might seem absurd. But these are not normal times especially for Casey Wasserman.

He oversees a sports marketing empire, runs a massive foundation, donates millions to politicians and charities, and chairs multiple civic institutions. Yet his most precarious role might just be his latest steering the 2028 Los Angeles Olympics while navigating a president intent on putting his own inimitable stamp on the Games. Calls already have come from columnists at the Los Angeles Times and San Francisco Chronicle for LA28 to push back against the Trump administration, even to cancel the event if necessary.

Mention Trumps name to Wasserman, though, and the response is measured, almost warm, or at least exceedingly diplomatic.

By total fluke of timing, I was the first person from L.A. to see the president of the United States in person after the fires, he says of their Mar-a-Lago meeting, noting that Trumps interest piqued when the discussion touched on Wassermans grandfather Lew, the legendary MCA-Universal boss who knew a thing or two about sweet-talking politicians on both sides of the aisle. We had a broad conversation, he goes on. Trump has been incredibly supportive and helpful to get us what we need to deliver these Games.

At this moment, Wasserman is sitting under the Coliseums south arch, site of the LA28 opening and closing ceremonies. Wearing an LA28 sweatshirt, jeans and gleaming Nike Air Maxes, hes framed by Olympic history this is where, at the 1932 Los Angeles Olympics, Babe Didrikson became the first athlete to win medals in both running and throwing events; where, during the 1984 L.A. Games, Carl Lewis won four gold medals. In the skies above him, an LAPD helicopter noisily circles. Its July, and the city is still traumatized by ongoing ICE sweeps and the recent invasion of National Guard troops.

Lets just hope were not in any danger, Wasserman jokes.

He is but not from the chopper. The real threat is the political minefield hes navigating with the leader of the free world.

Wasserman presented President Trump with a set of 1984 Olympic medals Aug.5 during an executive order signing ceremony in D.C. Win McNamee/Getty Images ***

The story of Wassermans emergence as one of L.A.s most powerful behind-the-scenes operators really starts in earnest on his 18th birthday, when he legally changed his name from Casey Myers to Casey Wasserman.

He grew up in Beverly Hills, born into privilege as one of only two grandchildren of Lew and Edie Wasserman, and would one day inherit a small fortune and after he filed the papers to change it a last name that even beyond Hollywood connotes power, poise, vision and, at times, ruthlessness.

Lew Wasserman a high school dropout who started out as an usher in Cleveland wasnt just a Hollywood powerhouse; he was one of the most influential figures in postwar America. During the 1940s, he rose through the ranks of MCA to become the most powerful music agent in town, then expanded into onscreen talent, guiding the careers of James Stewart, Bette Davis and Ronald Reagan. During the early 1960s, after acquiring Universal, Lew turned MCA into the industrys most powerful company and introduced bold new ways of doing business. (Packaging? He invented it.) Theres even a statue of him at Universal Studios Florida.

Casey Wasserman with girlfriend Jenny Chandler at the LACMA Art+Film Gala in 2024 Matt Winkelmeyer/Getty Images But with wealth and power often comes familial dysfunction. Casey has long made it clear to anyone who asks that he was not raised by his parents Lews daughter, socialite Lynne Wasserman, and stockbroker Jack Myers but rather by his grandparents. And when it comes to his father, who abandoned the family when Casey was 4 and was later convicted of money laundering, he doesnt mince words: My biological father was about as bad a human being as you could imagine, he says, tensing at the memory. There are bad dads, and there are absentee dads. My dad was a lot worse than that in a lot of ways. Ive never really talked about this, but he was not a good human being, and he was not part of my life at all. I didnt even go to my dads funeral. I didnt even know where he lived when he died. We had no connection.

Despite the family strain or maybe because of it Casey learned ambition at an early age. Even before graduating from UCLA, he was already making moves. In 1998, at just 24, he bought the Arena Football Leagues Los Angeles Avengers and four years later launched Wasserman Media Group, methodically building it into a global sports and entertainment powerhouse. Early acquisitions, like action-sports agency The Familie, revealed his knack for spotting undervalued niches. In 2006, he acquired Arn Tellems NBA and MLB practices, then U.K.-based soccer agency SFX, extending his reach across continents.

Though surrounded by Hollywood growing up Alfred Hitchcock and Sidney Poitier were frequent visitors to his grandparents home the familys strict no-nepotism policy kept him out of MCA. My grandfathers view was always, look, dont do what I do. Find what you love to do and do that, Wasserman recalls. What Casey loved, it turned out, was sports, or at least the business side of athletics. I was always fascinated with what was going on around here, he says, gesturing to the Coliseums executive suites. Part of that was due to my grandfather. He ran a business which made things that people thought were fun and cool and aspired to be in. But for him, it was a business. That was his lens. And I have that same kind of perspective.

Lew Wasserman with Alfred Hitchcock in 1962 Bettmann/Getty Images NBA commissioner Adam Silver calls him a trusted confidant. I probably talk to him on the phone as much as anyone else that I know, and its often just gossiping about the industry and trading information, Silver says. Hes been a sounding board to me on most of the major deals Ive done since Ive been commissioner.

Former Chicago Bulls star Derrick Rose, who signed with Wasserman as a rookie, recalls his early encouragement of big ambitions. I remember them laughing at me because I dreamed very big, says Rose. But Casey understood because of where he was at the time and how ambitious he was.

Unlike some of his competitors like WME, which went on a buying spree starting around 2010, scooping up a variety of assets like the Frieze Art Fair and the Miss Universe Organization, among others Wasserman remained relatively restrained in his focus, sticking almost entirely to sports. At least for a while.

Internally I was like, nope. This is what we do, and this is how were going to do it and were not going to stray. Were not going to pretend to do other things. Were not going to half-ass doing other things, he says.

Still, in the back of his mind, he was curious about the live music space, which he viewed as the next evolutionary step for a sports management company. An opportunity came during the pandemic when Tom Gores called, offering to sell Paradigms music vertical. Wasserman couldnt resist. A year later, he dipped his toe even further into the film and TV industry with his acquisition of management firm Brillstein Entertainment Partners. Wassermans music clients now include Coldplay, Chappell Roan and Kendrick Lamar.

What makes talent successful is pretty consistent, he says. Whether youre Brad Pitt or Yoshinobu Yamamoto on the Dodgers or Connor McDavid or Kendrick Lamar, they have a level of talent, a level of skill, and our job is to be a part of their team to harness that opportunity for them.

And then, in 2014, Wasserman got a phone call that would eventually afford him an opportunity to harness his own talents in a way hed never imagined.

It was L.A.s then-Mayor Eric Garcetti on the line, asking Wasserman for his thoughts on who could spearhead the citys bid to bring the Olympics to Southern California. Wasserman offered some suggestions. But a few days later, Garcetti called back and told him those names werent going to work. He did have one idea, though he wanted Wasserman to lead the effort. And he wasnt going to take no for an answer.

The L.A. Memorial Coliseum during the 1984 opening ceremony Steve Powell/Allsport/Getty Images It was a mix of factors that helped L.A. land the 2028 Summer Games. The city of Boston at one point was the lead candidate, but after initial polls showed the locals were firmly against it, Boston pulled out, opening a lane for L.A., where the population was more eager.

One of Los Angeles major advantages was the existing infrastructure, including stadiums (the Coliseum, Rose Bowl and SoFi) and major arenas (Crypto, Kia Forum and Intuit), not to mention that the city had already hosted two previous Olympics, both of which were considered financial successes. It ultimately became a two-city race between L.A. and Paris for the 2024 Games. But the International Olympic Committee decided to name two winners, giving 2024 to Paris and 2028 to L.A.

Were not building anything, but well have plenty of temporary construction, Wasserman says of L.A.s preparations for the Games. Our temporary construction spend in the past four months will make us the largest construction project in the history of America.

As chairperson for LA28, Wasserman oversees that project and juggles a slew of other responsibilities. Liaising between the local and federal governments and the Olympics, bringing on corporate sponsors, finding additional sources of funding from private donors (one of his LA28 innovations is offering venue naming rights to Fortune 500 companies). All this on top of his day job running Wasserman, his billion-dollar sports and entertainment agency.

Its a workload that would flatten most executives and it comes with an increased public profile that has meant more personal scrutiny than hes ever dealt with before. Last summer, for instance, the Daily Mail published a story delving into his private life, alleging that Wasserman engaged in serial affairs with employees, including an LA28 staffer who recently resigned. He disputes the facts laid out in the Mail and declines to comment beyond that but in 2021, he divorced his wife of nearly 20 years, producer Laura Ziffren (whose own grandfather, Paul Ziffren, chaired the 1984 Olympics), and is now with Chandler, who was his date at Mar-a-Lago.

Still, last summers tabloid headlines didnt diminish his milestone birthday bash in July 2024. The party was held at Santa Monicas Barker Hangar, and guests included luminaries from across the political and Hollywood spectrum. Bill Clinton, Nancy Pelosi, Gavin Newsom and Doug Emhoff were present, as was Bob Iger, Jim Gianopulos and Bob Kraft. A version of the industry-favorite deli Nate n Als, where he had once bonded over breakfast with his grandfather, was re-created, complete with a sign reading Lew n Casey, in the restaurants iconic retro orange typography.

You get the sense when speaking with Wasserman that the specter of his grandfather and the expectations that come with the Wasserman name weigh heavily. He clearly leans into his lineage but at the same time bristles at the notion that hes just another nepo baby.

One of the things I always wanted to do was create my own reputation, good or bad. I wanted it to be earned. I didnt want my reputation to purely be that I was Lews grandson. Theres nothing Im prouder of as a human being than being his grandson but thats not who I am.

The couple flanked NBA commissioner Adam Silver, a close friend, at Sun Valley in 2023. Kevin Dietsch/Getty Images ***

A few months after Wassermans meeting at Mar-a-Lago, President Trump effectively declared war on L.A.

In June, he sent thousands of National Guard troops into the city to assist with immigration enforcement efforts without alerting California Gov. Gavin Newsom or L.A. Mayor Karen Bass. For several weeks, the city was seething and felt like it was one tragic event away from toppling into even greater urban unrest after suffering through the wildfires earlier in the year and protests over President Trumps immigration policies.

Wasserman, Gov.Gavin Newsom and Mayor Karen Bass were on hand to receive the Olympic Flag in L.A. in August 2024. Leon Bennett/Getty Images A month later, President Trump proclaimed that he planned to put his own personal stamp on the 2028 Summer Games. He announced a White House task force that hed personally oversee. That task force would manage the various federal agencies providing security for the Games, giving the White House leverage over the proceedings. News of the task force prompted a growing chorus of voices calling on Wasserman and LA28 to stand up to the Trump administration and, if necessary, cancel the Games altogether.

Today with just 150 weeks before the torch arrives in Los Angeles Wasserman finds himself in the toughest of spots. But hes hardly alone. In the six months since Trump took office, scores of moguls and American institutions have found themselves being squeezed by the White House. Universities like Harvard and Columbia, white-shoe D.C. law firms, Hollywood corporations like Paramount, and even Trump-supporting tech bros have all faced unprecedented political pressure. (That $40 million Melania doc that Ratner is making? Thats Jeff Bezos way of bowing to the president.)

For Wasserman, it must be particularly galling. He landed the Olympic gig during Trumps first term and thought he was done dealing with Trump for good after the 2020 election until his reelection in 2024. Reacclimating to the new political realities has required some fancy footwork and probably explains some recent shifts in his political spending. Over the past eight months, this stalwart Democratic contributor has given more money to Republicans than ever before: $50,000 to the Johnson Leadership Fund, the political action committee founded by the speaker of the House, Mike Johnson; $50,000 to the National Republican Senate Committee, which aims to help elect Republicans to the Senate; and tens of thousands more to organizations tied to Sen. Lindsey Graham of South Carolina, Sen. John Cornyn of Texas, House Majority Leader Steve Scalise and Sen. Tim Sheehy of Montana, among others.

My political giving is representative of my job, not just in the Olympics but my job in the industries I work in, he insists. Youre not getting anything done if you only talk to people who think like you. He references an old antitrust investigation by the Justice Department under Attorney General Robert F. Kennedy in 1962 over MCAs ownership of Universal Studios and Decca Records. That investigation, he says, forced his grandfather to step up his profile in Washington.

Thats when he completely changed his perspective and engagement in Washington, he notes. And it changed the course of the entertainment industry with his ability to have influence on the political machine to support his industry. And I watched him do that.

Attorney General Robert F. Kennedy (right) investigated Lew Wassermans ownership of Universal Studios and Decca Records during the 1960s. Bettmann/Getty Images Those close to Wasserman say hes uniquely suited for this task. Casey is going to remain true to his values and the principles that hes lived by, says Silver. But he has that ability to engage across the aisle, whether its with the Democratic governor of California or President Trump, when necessary.

That engagement undoubtedly will prove to be fraught, especially considering some of Wassermans previously stated positions. In 2020, he had urged the IOC to loosen Rule 50, which would ease restrictions on podium protests and other forms of freedom of speech by athletes. Thats not something Trump will likely love. The president has publicly criticized athletes for social justice protests and called NBA players kneeling during the national anthem disgraceful.

Still, Wasserman says the calls for cancelling the Games are pointless. This notion that canceling them would somehow get [President Trump] to change his behavior is frankly naive, he says. We live in a complicated world, and it cant be all-or-nothing. Lets not be confused. Other than Texas and Florida, he got more votes in California than any other state in the union. We can say what we want, but 47 other states had less votes for President Trump than California did.

Its complicated, he goes on, as the chopper finally banks from the skies over the Coliseum and veers off into the distance. At certain times, Trump has had conflict with the city of L.A. At certain times, hes had conflict with the governor of California. My job is to make sure that these are Americas Olympics that are being hosted in Los Angeles. These arent L.A.s Games, these are Americas Games.

This story appeared in the Aug. 20 issue of The Hollywood Reporter magazine. Click here to subscribe.