Real Estate Forum – James Cappleman – Panelist -

James Cappleman began his career as a fifth-grade teacher in Houston. When one of his 11-year-old students was arrested for prostitution, he realized he wanted to do more for children facing severe psychosocial challenges. This calling eventually led him to Chicago, where he entered the Franciscan order and studied for the priesthood. Ultimately, recognizing that obedience was not his strongest suit, James left the order and pursued a career in social work. In Chicago’s Uptown neighborhood, which is home to the highest per capita rate of people living with chronic mental illness in the nation, he worked with individuals coping with multiple diagnoses, including mental illness, substance use disorder and HIV, as well as homelessness.

Encouraged by friends, James ran for alderman of Chicago’s 46th Ward, serving three terms from 2011 to 2023. His background as a social worker shaped his data-driven approach to city governance, where he emphasized the use of measurable outcomes to improve both his ward and the broader city. He collaborated with residents to develop the 46th Ward Master Plan, which prioritized public safety, expanded housing and promoted more vibrant local shopping. Nine years into his tenure, Uptown was 24th on Time Out’s ranking of the world’s coolest neighborhoods.

Recently, James has written a book on Chicago politics, which is currently under consideration for publication. Drawing on his social work perspective, the book examines the city’s chronic challenges and emphasizes the need to address root causes rather than relying on workarounds.