OREGON - Jeff “Ole” Olson, age 63, of Oregon, passed away on Monday, March 17, 2025.

Jeff was born on December 8, 1961, in Madison, Wis., the son of Richard and Joanne (Zurfluh) Olson. After graduating from Madison West High School in 1980, he traveled the country as a young man, eventually settling in Dallas, Texas. There he met the love of his life, Judy Lerch, and they were married at the Belo Mansion in Dallas on February 13, 1988.

With their two young children in tow and another on the way, Judy and Jeff returned to Madison in June of 1997 to be closer to family. Later that year however, Jeff suffered his life-changing spinal cord injury. Despite the resulting paraplegia, he never let that stop him.

Judy and Jeff raised three amazing, successful, and caring children. Jeff became a certified Arborist and together with his long-time business partner, Chris Heise, built a highly successful tree service business. He was especially proud of his entire crew at ArborSystems. Jeff prided himself on taking good care of both his employees and his customers - each of which received a hand-written letter of thanks when the job was done. There was a reason both tended to stay with him long-term.

In his spare time Jeff continued to enjoy hunting and fishing despite his limitations. He was also well-known for his love of woodworking, which he regarded as his therapy. He was an artist, spreading love through the pieces he created. Jeff cherished weekly Sunday dinners with his family and spending time with his dogs. And in this past year, becoming Papa to his new grandson, Otto, was the highlight of his life.

Jeff gave back tirelessly to the community. He was a regular donor to local fundraisers, coached his kids’ soccer and baseball teams, and was one of the first coaches of the West Madison Little League Challenger Division for kids with disabilities. He received the Gold Leaf Award to honor him for the work he did for Arbor Day events and education. He also mentored others as they navigated their own disabilities.

Jeff’s passion for life and infectious good humour were gifts he shared with all who loved him. He is survived by his wife, Judy; children, Carleigh (Kevin Gleason), Will, and Casey (Mary First); grandchild, Otto Gleason; father, Richard (Jeanette), sisters, Julie (Leo) Wasserburger and Cheri (Kyle) Olson Kreitzmann; brother, Jim (Tammy) Olson; sisters-in-law, Jodie Olson and Carol Lerch; brothers-in-law, Victor (Susan Marshall) Lerch and Mark Lerch; along with nieces, nephews, uncles, aunts, cousins and many close friends. He was preceded in death by his mother, Joanne Olson; brother, Greg Olson; father-in-law, Jack Lerch; mother-in-law, Erika (Paul) Lake; and sister-in-law, Gayle Lerch.

A celebration of life will be held at GUNDERSON FITCHBURG FUNERAL AND CREMATION CARE, 2950 Chapel Valley Road, Fitchburg, from 2 p.m. until 5 p.m., with a time of remembrance at 4 p.m., on Friday March 28, 2025.

In lieu of flowers, memorials may be made in Jeff’s name to Friends of Anderson Park, the Arbor Day Foundation, West Madison League (Challenger League), P.O. Box 44063, Madison, WI 53744 or a mental health organization of your choice. Or let his memory live on through planting a tree. Online condolences may be made at www.gundersonfh.com.

As Jeff always said, “There’s givers and takers- It's always better to be on the giving side.”

Gunderson Fitchburg
Funeral & Cremation Care
2950 Chapel Valley Road
(608) 442-5002

Jeff "Ole" Olson

December 08, 1961 - March 17, 2025

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