Robinson was regarded as a progressive in Woodrow Wilson's image. Robinson gained influence in the Senate and later served as Chairman of the 1920 Democratic National Convention. Robinson was re-elected to the Senate in 1918, 1924, 1930, and 1936. In 1923, the Senate Democratic floor leader Oscar Underwood, who served as the Senate Minority Leader, resigned due to illness. Senior Democratic Senator Furnifold Simmons was expected to take Underwood's place, but withdrew his name from consideration after Robinson challenged him for the position. By unanimous acclamation, Robinson became the Democratic leader, a position he would hold until his death in 1937.