In 2005, it was reported that de Jongh led all potential candidates to become the next governor of the U.S. Virgin Islands when the incumbent vacated his seat the following year. In 2006, he ran as a Democrat and won the Democratic Party primary defeating Lieutenant Governor Vargrave Richards and Senator Adlah Donastorg with 52.2% of the votes. He won the governorship in 2006 after defeating former Lieutenant Governor Mapp in a November 21 run-off election with over 57% of the vote.