After briefly working in the education and journalism fields, Willis read law with private tutors and was admitted to the bar in 1901.

He became interested in politics, but his early races for office were unsuccessful with the exception of his four-year stint as city solicitor for Ashland, Kentucky.

The end of World War II in 1945 brought sizable budget surpluses to the state, and disagreements over how to spend the excess funds spilled over into special legislative sessions.

Willis was not able to realize his campaign promise of eliminating the state income tax because the legislature expanded the budget far beyond what he proposed.

But he did forge a record of modest accomplishments, including constructing five tuberculosis hospitals across the state and significantly increasing funding for education.

[1] He simultaneously read law with private tutors, including future congressman Joseph Bentley Bennett and William Corn, a professor at Ada University.

[6] In 1916, he ran for a seat on the Kentucky Court of Appeals, but lost in the primary to Flem D. Sampson, who went on to win the general election.

[7] He took a brief leave of politics and served as an appeals agent for the Selective Service System during World War I.

[9] When Flem D. Sampson was elected governor in 1927, he appointed Willis to fill his seat on the Kentucky Court of Appeals.

[7] In 1928, Willis was elected to a full four-year term representing the Court's Seventh Appellate District.

[6] One factor influencing his victory was his ability to regain much of the black vote in urban centers such as Louisville, which had traditionally supported Republican candidates but had in recent years swung Democratic, because of the Republican Party's failure to deliver on campaign promises after winning elections.

[14] Governor John W. Bricker of Ohio, who did become the Republican vice-presidential nominee in 1944, had helped Willis in his gubernatorial race.

Upon Willis' victory, Bricker wired a friend to express jubilation, which turned out to have been unfounded: "Election showed definite trend in all areas against New Deal.

[16] Willis did not make wholesale dismissals of Democratic appointees at higher levels in the state government, owing in part to shortages of experienced people during the war.

[16] This cost him some Republican support, and both his lieutenant governor and attorney general began to oppose him on many matters.

[14] But his refusal to make wholesale dismissals may have produced more positive relations with the legislature, which did not pass legislation to strip the bulk of his gubernatorial powers, as it had done to Flem D. Sampson, the last Republican governor.

[18] Other accomplishments of Willis's administration included eliminating tolls on twelve of the state's thirteen major bridges, and expanding programs for dependent children and the elderly.

[6] Construction of five state tuberculosis hospitals—at London, Madisonville, Paris, Ashland, and Glasgow—was initiated and nearly 80 percent completed by the end of his term.

[2] In 1952, he failed in his bid to return to the Court of Appeals, having lost to Bert T. Combs, who later was elected as governor.