Jimmy

James H. Olson – known to all who loved him as Jimmy – passed away peacefully in his home surrounded by loved ones on April 26, 2026, in Milwaukee, Wisconsin, at the age of 71.

Born November 19, 1954, in Sycamore, Illinois, to James Olson and Ruth Odom, Jimmy was a true rolling stone, having made his home over the years in Illinois, Kentucky, Tennessee, California, Virginia, New Mexico, and Wisconsin. Wherever he landed, he left a mark – not just in the homes he built and repaired, but in the hearts of those who knew him.

A jack of all trades, Jimmy spent most of his working life in home construction – roofing, siding, installing windows, painting, fencing, building decks, and tackling any odd job that needed doing. He was hardworking, capable, and never too busy to help a friend or neighbor with a repair. His big heart showed itself in his willingness to show up, toolbox in hand, whenever someone needed a hand.

But if you asked anyone what they remember most about Jimmy, they'd likely smile and mention his jokes. He was a big jokester, always cracking one-liners and finding humor in the everyday. Even on the hardest days, he had a gift for putting a smile on your face.

Jimmy was preceded in death by his father, James Olson; his mother Ruth Odom; his stepmother, Ida, who raised him; his brother, Alan; and his precious daughter, Amy Lee Olson, who was born an angel.

He is survived by his sister, Marlene Davis; and his children: Jessica Robinson (Weylan), Jesse Olson (Marialuisa), Jayme Olson, and his chosen children, Neil and Jennifer Bullion – whom he loved as his own. He was a proud grandfather to Jade, Jezel, SheQuel, SheyLin, Jesse James II, and Christopher, and a great-grandfather to Romeo and Juniper. Jimmy also leaves behind countless nieces, nephews, extended family, and dear friends – too many to count, all of whom will miss his laughter and his generous spirit.

A Celebration of Life will be held in his honor on Saturday, May 30, 2026, from 3:00 p.m. to 5:30 p.m. at Pulaski-Cudahy Park Pavilion, 5400 S. Swift Ave., Cudahy, WI 53110. All who remember Jimmy – or who were touched by his kindness and humor – are welcome to attend, share a story, and celebrate a life well-lived.

In lieu of flowers, the family asks that you consider doing an unexpected act of kindness for a neighbor or sharing a good joke with someone who needs a smile – exactly as Jimmy would have done.