After law school, McCawley had a clerkship with Judge
Jose Gonzalez Jr. at the
U.S. District Court for the Southern District of Florida. In 1999, McCawley joined
Morgan, Lewis & Bockius in
Washington, D.C. a firm based in New York City and led by
David Boies who was establishing operations in
South Florida. As this was a small office, McCawley was often given the opportunity to represent the firm's large clients, companies such as
Del Monte Foods and
Carnival Cruise Line. McCawley was assigned to take on the case because of her experience volunteering with abuse victims in the
foster care system. McCawley was not the first to represent Giuffre but the case against Maxwell, who is also accused of recruiting minors for Epstein and others, brought new attention to the case. The firm decided to file for defamation because the
statute of limitations for criminal charges had expired. In December 2019, McCawley became an equity partner at Boies Schiller Flexner. By this point, she had been representing the victims in the Jeffrey Epstein case
pro bono for the past five and half years, including directly representing eight women and as co-counsel for three others. The unsealed transcripts led to criminal charges being filed against Maxwell. In December 2020, McCawley was appointed one of three co-managing partners at Boies Schiller Flexner. After filing a civil sex assault case against Prince Andrew in which he was scheduled to be deposed in March 2022, the BBC wrote in February 2022 that McCawley "is considered one of America's lead attorneys for sexual abuse cases". For her work representing victims of sexual abuse, McCawley was chosen as a finalist for
The American Lawyer Attorney of the Year. == Personal life ==