Selling stock in this company relieved its debt, and he bought a wholesale grocery for his brothers to run, and land in Madison, Wisconsin.
Progressivism was strong in Wisconsin, as expressed by Senator John J. Blaine and the newspaper Capital Times edited by William T. Evjue.
A wartime cabinet-level conflict involving foreign economic operations in Europe and North Africa threatened cabinet solidarity.
So Crowley became head of the Foreign Economic Administration in September 1943, with responsibility for Lend-Lease and Edward R. Stettinius Jr., was promoted to Undersecretary of State.
Though disguised, his banking misdeeds threatened to undo his place in political diplomacy, for instance years later when Henry Morgenthau Jr. or Arthur Vandenberg were checking his credentials.
Back in the business world, Crowley was named chairman of the Milwaukee Road in December 1945 and made it turn a profit until the mid-1960s.
He continued contact with the White House: President Dwight Eisenhower appointed Crowley to the United States Commission on Civil Rights in his second term, and he was known to have dined with Lyndon Johnson.