Key questions for a foreign diplomat in Washington DC were how to have his government’s concerns heard by the administration which was taken up with economic revival and implementing the New Deal and also would Roosevelt move from isolationism to internationalism? The chapter unravels how Ireland’s interests featured in official America’s foreign and domestic policies. It argues that the two Irish ministers, Michael MacWhite and Robert Brennan had contrasting abilities and personalities which affected how each fulfilled de Valera’s unrealistic instructions to secure Roosevelt and the State Department’s attention. Trade negotiations between the US and Ireland never formally commenced, despite MacWhite and Brennan’s efforts and throughout the period Roosevelt restated his opposition to intervention in partition. However, both diplomats prevented a diplomatic crisis when the US government protested to the Irish government about the illegal dissemination and sale of Irish Hospitals Sweepstake tickets in the US. By 1939, de Valera and Roosevelt accepted that international co-operation through the League of Nations had failed.