Senior Advisor to the Secretary for the Coast Guard Sean Plankey (left) shakes hands with the Secretary of Transportation Sean P. Duffy (right) during the 54th’ Secretaries’ Cup game at Fenway Park, Boston, Nov. 15, 2025. In 2003, “Secretary’s Cup” was pluralized when the U.S. Coast Guard moved to the Department of Homeland Security. (U.S. Coast Guard photo by Petty Officer Second Class Janessa Warschkow.)