He was also a co-founder and member of the board of directors of the National Security Network. He was appointed to the American Bar Association's Standing Committee on Law and National Security in 2010. Wolosky has also served as an adjunct professor at the School of International and Public Affairs, Columbia University Guantanamo As Special Envoy for Guantanamo Closure from July 2015 to January 2017, Wolosky served as chief U.S. diplomat in connection with Barack Obama's efforts to close the Guantanamo Bay detention camp. Among other responsibilities, he led the Obama Administration's final diplomatic efforts to reduce the detainee population before the end of Obama's term, by transferring detainees who had been unanimously approved for transfer by the United States Secretary of Defense, State, Attorney General, Secretary of Homeland Security, Chairman of the Joint Chiefs of Staff, and Director of National Intelligence. During his 18-month tenure as Special Envoy, Wolosky completed the transfer of 75 detainees to 15 countries, or almost 40% of all such transfers during President Obama's eight-year term in office. Since closure of the Office by the Trump Administration, the U.S. government has lost track of several of the Guantanamo detainees Wolosky arranged to release. Legal career 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. 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, 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. In October 2019, Wolosky was appointed Independent Monitor of Deutsche Bank