He was admitted to the Ohio bar in 1919.[2] After graduating from Reserve Law School in 1920, he worked briefly for the private law firm of F. Stanley Crooks.[2] Afterwards, he worked as the assistant City Attorney for Columbus (1923–1928), assistant Franklin County prosecutor (1928–1931), was elected to the Ohio House of Representatives (1933–1935), and served as majority floor leader while a state legislator in 1935.[1][2][3]
During 1935, the Republicans of Columbus selected him as their candidate to run for mayor.[2] He won the 1935 mayoral election defeating incumbent Democratic mayor Henry W. Worley. Gessaman became the 42nd mayor of Columbus, Ohio, the 38th person to serve in that office, and served Columbus during the Great Depression.[1] After one term in office he was defeated in the 1939 mayoral election by Republican opponent Floyd F. Green.[1] After his defeat for reelection as mayor, he was later elected as a judge to the Franklin CountyCommon Pleas Court in 1943.[1][3] He served as judge for 30 years.[1]
He married Marie C. Sommer in 1922 and had three children - Ann, David G., and Richard.[2] His youngest son Richard was killed in Korea in 1954.[3] Two years after his retirement from the Franklin County Common Pleas Court he died on August 20, 1975.[3] He is interred at Union Cemetery in Columbus, Ohio.[3][4]