Wilson’s Presidency both overlapped with and was in many ways definitive of the politics of the Progressive Era (approx. 1890-1920).

The term “Progressive” was broadly defined, encompassing a wide array of policies and ideologies – often in contradiction with one another – which sought to mitigate social and economic inequalities at the turn-of-the-20th century.  The era witnessed the rapid expansion and overcrowding of cities, inadequate housing, unregulated labor, poor public health, farmer indebtedness and sharecropping – especially for southern Blacks, child labor, and the emergence of a wealth gap in which 1% of Americans owned nearly 90% of the nation’s wealth. While their solutions differed and often conflicted, Progressives shared the view that a proactive, expanded government was necessary to fix society’s ills.  

Progressives in both the Republican and Democratic Parties (including, but not limited to, socialists, populists, and anarchists) sought solutions in the form of child labor laws, women’s suffrage, unionization, public health services, Black civil rights, and economic regulation and taxes as well as immigration restriction, segregation, and the prohibition of alcohol. All of these ideologies could fall within the “Progressive” umbrella.

Woodrow Wilson claimed his place within the Progressive movement with his economic reform package, "the New Freedom." This agenda, which passed Congress at the end of 1913, included tariff, banking, and labor reforms and introduced the income tax. Wilson also expanded the executive branch with the creation of the Federal Reserve, the Federal Trade Commission, and the Internal Revenue Service. His emphasis on efficiency and bureaucracy fit him squarely within the Progressive movement. 

During Wilson’s terms, Congress passed two constitutional amendments: prohibition (18th); and women's suffrage (19th)—both Progressive agendas. Another amendment was ratified while Wilson was President:  direct election of Senators (17th) on April 8th 1913. (The 16th amendment, which concerns income tax, was ratified in February 1913, after Wilson was elected but before he took office. The ratification was proclaimed by Taft’s Secretary of State, Philander Knox). 

Wilson’s Progressive legacy was also solidified through the appointment of his close friend Justice Louis Brandies to the Supreme Court as the first Jewish American to sit on the nation’s highest court. Justice Brandeis was a staunch proponent of the right to free speech and the right to privacy while he supported the regulation of business and anti-monopoly legislation championed by Wilson’s economic plan.

Wilson also embraced and encouraged new technology. He opened the Panama Canal, started airmail service, endorsed the creation of an interstate highway system, appeared in one of the first filmed campaign advertisements, used a microphone for the amplification of his voice, and witnessed the birth of radio.

These accomplishments, however, were all too often achieved at the expense of African Americans, women, immigrants, and Native Americans. Legal scholars have revealed the ways in which the income tax codes and banking policies often disadvantaged African American families. What is more, Wilson couched his embrace of segregation as part of his Progressive commitment to efficiency, arguing (insincerely) that segregation reduced friction among federal workers and increased productivity. And though Wilson vetoed the 1917 Immigration Law which established the Asiatic Barred Zone and a Literacy Test for entry, along with other restrictive measures, he nonetheless voiced support for much of the law and his veto was ultimately overridden.