Joseph Caldwell Sr., hailing from Marvel, Arkansas, is more than just the owner of TailoRite Complete Clothing Care, founded in 1956. He’s a Korean War veteran, a family man, and a dedicated entrepreneur whose journey began after graduating from the Metropolitan School of Tailoring in 1956. Not content with only tailoring, he pursued business studies at IIT, Marion Business School, and the University of Maryland.

Caldwell’s commitment to community service and civil rights shines through his founding of the Gentleman’s Tailors Club, organizing fundraisers, and providing tailoring services for civil rights leaders. He’s been a prominent figure in Chicago’s business and social scene, serving on boards like Seaway Bank, the YMCA, South Central, the Chatham-Avalon and the Chatham Business Association. But beyond business, Caldwell’s heart lies in supporting political initiatives and social causes, from fundraising for Harold Washington’s mayoral campaign to participating in the March on Cicero. Joseph Caldwell Sr. remains an inspiration, a leader, and a vital part of his community.

Mr. Caldwell is married to Barbara Caldwell, together they have four children, nine grandchildren and three great grandchildren.