In 2001, Wolosky joined Boies, Schiller & Flexner LLP, the prominent U.S. law firm led by David Boies whose partners are known for high-profile matters such as the representation of Al Gore in the contested 2000 U.S. presidential election, representation of the U.S. Government in its anti-trust dispute with Microsoft, and representation of American International Group and its former CEO, Maurice R. Greenberg. Wolosky has led or co-led some of the firm's high-profile matters in recent years, including the firm's representation of Greenberg, its representation of former RNC Vice Chair Elliott Broidy in litigation against Qatar, its terrorism financing case against Bank of China; and "Restis v United Against Nuclear Iran", a precedent-setting private defamation case in which the United States Government asserted the state secrets privilege, resulting in a victory for Wolosky's client UANI. Wolosky also served as co-lead counsel to certain of the 9/11 families in connection with a multibillion-dollar federal court judgment entered against Iran; and as lead counsel to a major international corporation in matters arising out of an alleged assault by Dominique Strauss-Kahn, the former managing director of the International Monetary Fund.