[1] He is currently co-chair of the Litigation Department and a member of the Management Committee at Jenner & Block LLP[2] Wolosky grew up in The Bronx and attended Columbia Grammar & Preparatory School in Manhattan.

Before attending law school, Wolosky worked as a research assistant for a Harvard University project focused on Soviet political and economic reform.

Wolosky served as Director for Transnational Threats on the United States National Security Council in the White House Office, under President Bill Clinton and George W. Bush.

Wolosky's pursuit of Bout served as a loose basis for the character Jack Valentine (played by Ethan Hawke) in the film Lord of War.

During his time at Boies Schiller, Wolosky led or co-led some of the firm's high-profile matters, including the firm's representation of Greenberg, its representation of former RNC Vice Chair Elliott Broidy in litigation against Qatar,[8][9] its terrorism financing case against Bank of China;[10] 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.

[15] Wolosky has also represented Fiona Hill, a former advisor on the United States National Security Council, in the 2019 impeachment hearings of Donald Trump[16] and opposed the White House's efforts to prevent her testimony.

At Paul Weiss, he worked principally with and was mentored by Ted Sorensen, the seventh White House Counsel under John F. Kennedy and Lyndon B. Johnson.