#201: Building a Local Legacy: Inside Jimmy Holmes' Life, Business, and Music

In this episode of the Kankakee Podcast, host Jake LaMore sits down with one of the community’s most requested guests—Jimmy Holmes, owner of the iconic Jimmy Holmes Clothing. Known for his signature personality and legendary status around Kankakee, Jimmy shares the captivating story of his family’s journey from Texas and Elgin, Illinois, to Bourbonnais (and now Bradley), where the Holmes family has outfitted generations since 1957.

Jake and Jimmy dive into decades of stories, from big band adventures—Jimmy’s father once sang with Tommy Dorsey’s band and even had a boxing match refereed by John Wayne—to running Gentleman Jim’s jazz club, crossing paths with up-and-coming rock legends, and forging deep community ties in Kankakee County. Jimmy opens up about the legacy of the family business, the evolution of fashion, hard-won lessons in salesmanship, and the deep roots of faith that ground him.

The episode explores Jimmy’s multi-faceted life: athlete, singer-songwriter, mentor, and community stalwart. He reflects on the joys and challenges of small business, shares advice on looking your best (and keeping romance alive), and even brings his guitar along for a heartfelt live performance of “If Tomorrow Never Comes.” Along the way, listeners will hear tales of local music legends, the changing face of Kankakee, and why Jimmy believes connection, forgiveness, and faith are the true riches in life.

What drives Jimmy to keep the business going after 50+ years? How has the men’s clothing industry changed, and why is service with a personal touch more important than ever? What does it mean to be considered a “Kankakee legend”—and how does Jimmy feel about the title? Tune in for laughter, wisdom, and a story as unique as the town itself.

As always, Jake and Jimmy remind us of the value of community and the power of staying true to your roots. Don’t miss this celebration of Kankakee’s past, present, and future—one story, one song, and one sharp suit at a time!