One of Dudley's first large accounts was AT&amp;T, a client he would keep until his death in 1966. Dudley was also retained to mount a campaign to launch the political career of Woodrow Wilson, then president of Princeton University. Dudley's client in this endeavor is unknown and he would carry the details of the assignment to his grave. He last spoke about the Wilson project in 1959 to say only that it was a "highly confidential matter", exposure of which would be "damaging to our profession". Prior to the Triangle Shirtwaist Factory fire of 1911, Dudley helped organize opposition to the mandatory installation of sprinklers in warehouses at the behest of another client, the Protective League of Property Owners. Following World War II, it was revealed Dudley had worked as a middle-man to funnel payments from DeWitt Wallace to Lawrence Dennis; Wallace had hired Dennis to write "smear pieces" against Henry A. Wallace for "Reader's Digest".