James Robert Boles

James Robert Boles, age 16, of Prescott, Wisconsin, passed away unexpectedly on March 3, 2026.

James was born December 9, 2009, to Jeremy and Roxan Boles (Johnson). James decided he was ready to join this world through a snowstorm (although he hated the cold weather). This sweet boy presented so many surprises for us. He was early by two weeks, he was a boy (we were told a girl), and he blessed us with many challenges we were given the privilege to work through. James was the toughest person we have ever known. Through so many procedures, surgeries, hospital stays, and therapies, he would always come out stronger.

James was the best big brother to John and Jaxon. He loved keeping an eye on them from a distance. He was their biggest cheerleader through all their sports and activities. His brothers sure loved him too. They knew when James needed one of his four preferred movies changed, when he was ready for his milk and Teddy Grahams, what made him laugh, and what toys would make him happy.

He was the best son anyone could ask for too. His patience was inspiring. His happiness and contagious smile could light up any room, which we believe allowed him to have many exciting experiences that many people wouldn’t have gotten.

He was a lover of all things water, lights, music, noisy toys, bridges, and swings. We could always get him to giggle by opening and closing the car windows, sneezing, stretching a tube toy, or making the sound of a buzzing bee.

He loved holding hands, having his arms rubbed, or getting fingers run through his hair. On the other end of the spectrum, he despised getting his ears cleaned or teeth brushed.

He was infatuated with watching a video of himself when he was still an infant, blowing raspberries and saying “dadadadadadada.” Another favorite was a clip from Alvin and the Chipmunks where they sang “Gotta Love Cheeseballs.”

Our sweet boy, Jamesie, loved riding the school bus. When we would say, “Let’s go find Gary (his school bus driver),” he would look out the window, get out of his chair at the kitchen table, and walk to the back door so he could get ready for his ride.

James is survived by his parents, Jeremy and Roxan Boles (Johnson); his brothers, John and Jaxon Boles; grandparents, Jim and Lori Boles, Robert Johnson, and Karol & Jeff Williams; Aunt Jolene Johnson; Uncle Troy Johnson; Aunt and Uncle Jessica & Josh Millar with cousins Maysie and Natalie; Aunt and Uncle Josh and Trina Boles with cousins Adeline, Ronald, and Vivian; Aunt and Uncle Jake and Nikki Boles with cousins Harley and Oakley; and Aunt and Uncle Jordan and Mariah Boles with cousins Clinton and Colton, as well as many other loving extended family members, friends, and supportive people.

James was preceded in death by his great-grandparents Stan & Bev Boles, Jeannie & Roger Esperson, Ronald Anfinson, Lloyd & Viola Johnson, and John & Doris Kittleson, as well as family member Jennifer Coomer.

A Funeral Service for James Boles will be at 11:00am on Monday, March 9, 2026, at St. Paul's Evangelical Lutheran: 1061 Orrin Rd, Prescott, WI 54021. A Visitation will start at 10:00am until the start of the Service. Burial will be at Pine Glenn Cemetery in Prescott at 12:15pm. Following the Burial a Celebration of Life will be held at Ridgetop in Prescott from 1:15pm-4:15pm.

In lieu of flowers, please consider donating in honor of James to:

Prescott School District Special Education Department, Children’s Hospital & Clinics of Minnesota,Gillette Children’s Hospital, St. Croix Therapy, KAT6 Foundation.

Arrangements are entrusted to O’Connell Family Funeral Home and Cremation Services of Prescott. For more information or to share a memory, please visit www.oconnellfuneralhomes.com or call 715-262-5404.