Off-duty Chicago firefighter killed in crash
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June 06 13:59:41, 2025
Timothy John O’Leary’s journey began in Lake Geneva, Wisconsin, when he was just 18 years old. He was riding in a car that crashed, and as he watched firefighters work tirelessly to stabilize his broken leg, something shifted inside him. He felt a calling, a desire to be that source of strength and hope for others. That decision led him to join the Chicago Fire Department, a path he pursued with unwavering dedication for nearly three decades.
Tragically, it was another accident—a collision on Interstate 43—that ultimately took his life. It happened late on a Tuesday night when O’Leary, 54, was heading southbound in his Toyota SUV. He struck the back of a semi-truck near Wisconsin Route 140, and first responders found his SUV wedged perilously beneath the massive trailer. The force of the impact shattered the rear window, allowing a paramedic to climb through and assist while the crew worked diligently to free him from the wreckage.
By the time O’Leary was safely extricated, emergency services had already mobilized swiftly. Within minutes, he was on a stretcher and in an ambulance, en route to Beloit Memorial Hospital. However, despite their best efforts, he succumbed to his injuries shortly after arrival, at 10:18 p.m., as confirmed by Barry Irmen, a spokesperson for the Rock County medical examiner’s office.
Laura Bundy-O’Leary, O’Leary’s wife, described him as not only her husband but also her best friend and soulmate. They had been planning their future together—O’Leary had even expressed his intention to retire within the year. Instead, her world crumbled around her when Wisconsin State Police arrived at their Chicago home with devastating news. Her search for answers had been frantic and heartbreaking, culminating in a gut-wrenching realization that he might never return home.
O’Leary hailed from an Irish-American family on Chicago's Northwest Side. He grew up surrounded by five siblings, and his legacy lives on through his three biological children and two stepchildren. One of his sons, John, has already begun following in his father’s footsteps. After completing a two-year paramedic program at Loyola University Medical Center, John now aspires to become a firefighter himself. In fact, he’s currently enrolled in the police academy, continuing the family tradition of public service.
O’Leary’s impact extended far beyond his immediate family. Colleagues and friends fondly recall his selflessness and generosity. He was known for going above and beyond, whether it was delivering a baby or finding someone in need. Many even named their children after him, a testament to how deeply he touched people’s lives. Laura remembered him as someone who could make her laugh with just a glance, someone whose eyes sparkled with kindness and humor.
His final years were spent working alongside Captain Sam Kamberis at Engine 125. Kamberis described O’Leary as a firefighter who embodied professionalism and commitment. His colleagues respected him, and the community admired him. Now, as the Chicago Fire Department prepares to honor his memory, tributes pour in from all corners of the city.
A visitation is scheduled for Monday evening at Cumberland Chapels, located at 8300 W. Lawrence Avenue. On Tuesday morning, a funeral mass will take place at St. Eugene Parish, 7958 W. Foster Avenue. Friends, family, and fellow firefighters will gather to celebrate his life and mourn his loss.
Laura reflected on their journey together, recalling countless moments filled with laughter and love. She spoke of his gentle spirit and how he always put others before himself. “He was my everything,†she said softly, her voice breaking with emotion. “Now, I have nothing but memories, and they’re bittersweet.â€
As the city of Chicago comes together to bid farewell to one of its bravest, it’s clear that Timothy John O’Leary left an indelible mark on everyone fortunate enough to cross paths with him.