Casey Wasserman was photographed Aug. 8 at the Los Angeles Memorial Coliseum. Styling by Ivan Barychnikov Zegna suit, shirt, tie; Oliver Peoples glasses; Rolex watch. Photographed by Kurt Iswarienko; wasserman Grooming by Jenna Nelson 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 Party's 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 who'd promised revenge on his political foes. Related Stories TV Glen Powell and Eli Manning: Meet Hollywood's Most Unlikely 'Powers' Couple Business Who the F*** Is Marc Maron Without Podcasting? He's About to Find Out Photographed by Kurt Iswarienko 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 hadn't seen him in years. "I don't know if I'm 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 Trump's 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 Trump's interest piqued when the discussion touched on Wasserman's 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 Coliseum's south arch, site of the LA28 opening and closing ceremonies. Wearing an LA28 sweatshirt, jeans and gleaming Nike Air Maxes, he's 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. It's July, and the city is still traumatized by ongoing ICE sweeps and the recent invasion of National Guard troops. "Let's just hope we're not in any danger," Wasserman jokes. He is - but not from the chopper. The real threat is the political minefield he's 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 Wasserman's 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 - wasn't 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 industry's most powerful company and introdu