After 1952, Dawson also became closely aligned with the political machine in Chicago, collaborating often with Mayor Richard J. Daley.

He continued his studies at Fisk University, a historically black college in Nashville, Tennessee, where he graduated magna cum laude in 1909.

With the entry of the U.S. into World War I, Dawson served in France as a first lieutenant with the 366th Infantry Regiment of the United States Army from 1917 until 1919.

Dawson entered politics, becoming a member of the Republican Party in 1930 as a state central committeeman for the First Congressional District of Illinois.

In addition to influencing national policy, he acted as a mentor for rising young black politicians in Chicago, such as Archibald Carey Jr., helping with their elections and federal appointments.

During his tenure in the House, Dawson was a vocal opponent of the poll tax, which in practice was discriminatory against poorer voters.

[3] Since the end of the nineteenth century, poll taxes were among a variety of measures passed by southern states to disfranchise most black voters and tens of thousands of poor whites as well, particularly in Alabama through the 1940s.

In 1952, Dawson was the featured speaker at the first annual conference of the Regional Council of Negro Leadership (a civil rights organization), held in the all-black town of Mound Bayou, Mississippi.

Since the Civil War, most blacks had been allied with the Republican Party, as it had emancipated the slaves and led the movement for amendments to grant them citizenship and the franchise.

In the predominantly African-American wards, Dawson acted as his own political boss, handing out patronage and punishing rivals just as leaders of the larger machine did, such as Richard J. Daley.