Casey Wasserman built an empire on connections, inherited wealth, and carefully cultivated power—but now those connections threaten to unravel everything he’s spent decades building.
As chair of the Los Angeles 2028 Olympics organizing committee and founder of one of entertainment’s most powerful talent agencies, Wasserman positioned himself as the ultimate connector between sports, entertainment, and global power brokers.
Then came the Jeffrey Epstein emails.
Released by the Justice Department on January 30, the correspondence between Wasserman and Ghislaine Maxwell—Epstein’s convicted accomplice now serving 20 years for sex trafficking—revealed messages no executive wants made public, especially one leading the world’s biggest sporting event.
The Dynasty Behind the Empire
Wasserman didn’t build his agency from nothing. His grandfather, Lew Wasserman, was one of Hollywood’s most powerful figures in the 20th century, running MCA before selling it to Matsushita Electric for $6.5 billion in 1990.
Lew took Casey under his wing as a teenager, providing access to an extensive network and vast fortune that would prove invaluable when the younger Wasserman founded his agency in 1998.
The agency expanded rapidly through aggressive acquisitions, including legendary basketball agent Arn Tellem and powerful soccer agency SFX. Today, Wasserman’s roster includes Kendrick Lamar, Connor McDavid, and Evan Mobley—though finding a complete client list recently became harder after the agency scrubbed relevant pages from its website.
Power, Parties, and the Olympic Prize
Wasserman cultivated a public persona as the quintessential mogul. His 50th birthday party featured Robert Kraft, Bob Iger, Bill Clinton, Nancy Pelosi, Gavin Newsom, and Doug Emhoff, with Imagine Dragons providing entertainment.
In 2014, Los Angeles Mayor Eric Garcetti tapped Wasserman to lead the city’s Olympic bid. Three years later, L.A. secured the 2028 Summer Games.
He retained both positions for now—though mounting pressure from departing clients and public scrutiny threatens that status quo.
The Emails That Changed Everything
The 2003 correspondence between Wasserman and Maxwell revealed inappropriate exchanges that Wasserman now publicly regrets. At the time, he was married to fellow entertainment executive Laura Ziffren.
In the emails, Wasserman asked Maxwell questions like:
So what do I have to do to see you in a tight leather outfit?
Maxwell responded by offering the kind of massage that could “drive a man wild.”
These exchanges occurred months after Wasserman joined Maxwell, Bill Clinton, Kevin Spacey, Ron Burkle, Chris Tucker, “about four women ages 20 to 22,” and Epstein himself on a two-week trip to Africa aboard Epstein’s Boeing 727—the infamous “Lolita Express.”
The Africa Trip
Spacey told the Los Angeles Times the 2002 journey aimed to “raise awareness and funds for HIV/AIDS” and included an “unforgettable day with Nelson Mandela.”
That plane would later become synonymous with Epstein’s sex trafficking operation, used to transport young girls across international borders.
Wasserman issued an apology shortly after the emails surfaced, emphasizing he had no relationship with Epstein beyond that single international trip. A 2024 Daily Mail story alleged Wasserman is a “serial cheater” with a “chronic condition of sleeping with people who work for him.”
He’s currently dating Jenny Chandler, who initially worked as a flight attendant on his private jet.
The Exodus Begins
Artists didn’t wait for explanations. Singer Bethany Cosentino of Best Coast became the first to publicly leave, followed quickly by major names including Chappell Roan, Wednesday, Orville Peck, and Beach Bunny.
Roan’s statement captured the sentiment driving departures:
I hold my teams to the highest standards and have a duty to protect them as well. No artist, agent, or employee should ever be expected to defend or overlook actions that conflict so deeply with our own moral values.
Among athletes, only former USWNT star Abby Wambach publicly announced her departure as of this writing.
Many departing clients called for Wasserman to resign from both the agency and LA2028 organizing committee.
The Olympic Committee’s Response
LA2028 held an emergency board meeting Wednesday and emerged with a unified message: everything’s fine.
LA28 takes allegations of misconduct seriously, and our Board is committed to thoroughly reviewing any concerns related to the organization’s leadership.
The committee claimed outside counsel reviewed Wasserman’s associations with Maxwell and Epstein, concluding they “did not go beyond what has already been publicly documented.”
Translation: they’re betting this story disappears or becomes manageable by 2028.
Political Connections Run Deep
One connection between Wasserman and Epstein remains uncontroversial in certain circles: steadfast support for Israel. Wasserman donated $525,000 to Friends of the IDF in 2019 and visited Benjamin Netanyahu in Israel just two months ago, securing a photo opportunity with the Israeli prime minister.
What Happens Next
The LA2028 board’s confidence hinges on one assumption: that public interest will fade and departures will slow.
But managing questions about your chairperson’s documented relationship with both Epstein and his convicted accomplice becomes exponentially harder if clients continue abandoning ship.
When you’re forced to split hairs about exactly how associated you were with Jeffrey Epstein, you’ve already lost the narrative battle. Wasserman built his empire on connections—but some connections carry costs that even billion-dollar fortunes and Olympic chairmanships can’t offset.
Whether those costs ultimately include his positions atop both the agency and LA2028 depends entirely on how many more clients decide their moral values conflict too deeply with remaining silent.