Jason Lee: Chicago’s Shadow Mayor Navigates a Tumultuous Year
Jason Lee, widely considered Chicago’s shadow mayor, finds himself navigating a turbulent period alongside Mayor Brandon Johnson. Johnson’s first year in office has been fraught with challenges, including a difficult budget process marked by the mayor’s own missteps, the failure of his “Bring Chicago Home” referendum, and a protracted struggle surrounding the Chicago Public Schools CEO, culminating in the mass resignation of Johnson’s appointed school board. These setbacks have intensified the pressure on both the mayor and his senior advisor.
Adding to Lee’s workload is a personal challenge: a flare-up of Crohn’s disease. Further complicating matters is the controversy surrounding his decision to vote in Texas during the November presidential election, despite residing in Chicago. This decision, he explains, was a fulfillment of a promise to his late mother, U.S. Rep. Sheila Jackson Lee, to support his sister, Erica Lee Carter, in her campaign for the vacant congressional seat. Lee maintains that his commitment to managing his health and fulfilling this familial obligation doesn’t impede his ability to perform his duties.
Lee acknowledges the intense scrutiny inherent in Chicago politics, drawing parallels to the challenges faced by former Mayor Rahm Emanuel. He emphasizes that his role in the city’s highest echelons is a choice, reflecting his belief in Mayor Johnson’s vision. He is pragmatic about the transient nature of high-level political positions, stating that he will continue his service as long as he feels he is contributing meaningfully. He plans to move on without resentment should that time come.
Lee’s path to becoming Johnson’s right-hand man is a unique one. Son of a civil rights champion, he embarked on a journey from Eagle Scout to Morehouse College, Harvard University (twice, earning a trifecta of master’s degrees in religion, ethics, and politics), and a stint as a Wall Street investment banker before eventually finding his calling in community organizing and politics. He chose Chicago as his platform for social change, initially catching the attention of Mayor Johnson. Their collaboration began with Johnson’s invitation to join his team, describing their working relationship as being “immediately on the same wavelength.” This led to roles in several key campaigns, including Johnson’s own mayoral run, providing invaluable experience navigating the intricacies of Chicago politics.
Lee’s mentor, Harvard University professor Brandon Terry, describes him as exceptionally intelligent, even a genius. Terry has encouraged Lee to pursue his own political career, but acknowledges the personal sacrifices involved. Lee’s upbringing, marked by his mother’s demanding career as a congresswoman, has shaped his perspective on the cost of public service. His father, Elwyn Lee, a vice president at the University of Houston, speaks of the toll that Sheila Jackson Lee’s dedication to her work took on Jason and his sister, while also highlighting Jason’s instrumental role in managing his mother’s final months and planning her funeral. Lee’s sister, Erica Lee Carter, currently serving her mother’s congressional term, emphasizes her brother’s unwavering compassion and dedication to positive change. His career trajectory, marked by intellectual pursuits, financial success, and ultimately a commitment to social justice, paints a picture of a complex and driven individual at the heart of Chicago’s political landscape.