Chester Phipps was the Governor of the Southern Confederation and a leading figure in the Liberal Party of the Confederation of North America in the 1910s and 1920s.
After the formation of the Friends of Black Mexico under Howard Washburne of Southern Vandalia, some Liberal members of the Grand Council supported nominating Washburne for Governor-General in the upcoming 1918 Grand Council elections. However, the F.B.M.'s involvement in the Chapultepec Incident of January 1916, which nearly led to war between the C.N.A. and the United States of Mexico, apparently caused second thoughts among the Liberal leadership. Governor Phipps was among those who opposed allying the Liberal Party with the F.B.M., and at the Liberals' national convention prior to the elections, Phipps was able to gain the party's nomination for himself.
During the campaign, Phipps argued that the election of a People's Coalition majority would mean "more of the same," presumably hoping that the North American electorate had grown tired of the Coalition's policies of government-subsidized businesses and isolationism. However, the P.C. candidate, Councilman Calvin Wagner of Indiana, accepted Phipps' accusation. "If by more of the same, Governor Phipps means still greater prosperity and continued peace and tranquillity, then I plead guilty to that desire."
The P.C. under Wagner had no trouble defeating the Liberals under Phipps, and Wagner became Governor-General in February 1918. However, what neither Wagner nor Phipps realized at the time was that prosperity brought its own problems, and those problems would soon lead to a national wave of discontent. Washburne inadvertantly contributed to the national discontent by transforming the F.B.M. into the League for Brotherhood in May 1920, creating a vehicle for those who sought to reject the values of modern civilization.
By 1922, there remained a large minority within the Liberal Party who wished for Washburne to lead the party in the upcoming Grand Council elections. Phipps remained opposed to Washburne, saying on 4 August 1922, "Mr. Washburne is a saint. But saints are notoriously poor politicians." Phipps was again able to prevent Washburne from gaining the nomination, which went to Councilman Henderson Dewey of Indiana. Unlike Phipps five years before, Dewey was able to defeat Wagner in the 1923 Grand Council elections.