Chicago occupies a special place in socialist and working-class history. International Workers’ Day commemorates the infamous Haymarket affair of 1886, which occurred during the titanic struggle for the eight-hour day. It is the city where the Industrial Workers of the World held its founding convention in 1905; it’s where the split between US Socialists and Communists occurred in 1919; and it’s where the roiling conflicts over Vietnam, civil rights, and Black Power came to a head at the 1968 Democratic National Convention. 

In recent years, Chicago has lived up to its historic role as one of the central hubs of labor militancy and political radicalism. The 2012 Chicago Teachers’ Union (CTU) strike was a milestone in contemporary labor history, and prefigured the wave of public education strikes that began in 2018 and continues to sweep across the country. That strike helped to stimulate a movement against the city’s deeply entrenched political establishment, which began to bear fruit with the election of Carlos Ramirez-Rosa, an outspoken socialist and community activist, to city council in 2015. Earlier this year, a new wave of self-identified socialists were elected to city council, a historic development that made international headlines. 

Members of the Democratic Socialists of America (DSA) have played an important role in building the city’s rising new left, and in taking on the infamous Chicago Democratic political machine. Here, Chicago DSA (CDSA) activist Lillian Osborne talks to fellow CDSAer and National Political Committee (NPC) member Marianela D’Aprile about the political situation in Chicago and the prospects for taking the movement even further.