Wittpenn became interested in politics when he gave a speech for James J. Murphy at a convention in Jersey City. Murphy lost the election, but Wittpenn's speech was remembered. He formally entered politics in 1904 as one of the
Hudson County, New Jersey, supervisors. His run for mayor of
Jersey City, New Jersey, was in 1907 against the Republican incumbent
Mark Fagan. Whitpenn remained in office until 1912 when he lost to
Frank Hague. While in office he appointed
Cornelia Foster Bradford to the
Board of Education. While mayor he saw the completion of the
Jersey City Medical Center begun under Mayor
Mark Matthew Fagan.
Later career In 1916, Wittpenn, the comptroller of customs at the New York Customs House, was nominated by the Democratic Party for governor.
Frank Hague is believed by many to have connived with
Walter E. Edge, the Republican candidate, to help Edge win by a relatively slim 7,430 votes by not encouraging Democrats to vote for Wittpenn. President
Woodrow Wilson named Wittpenn as the civilian overseer, of the
Port of New York. Wittpenn ran for Governor again in 1916, but was not elected. Henry registered for the draft as "Henry Whitpenn" but did not serve. In March 1929 Wittpenn was appointed as a State Highway Commissioner by Governor Lawson. ==Personal life==