Mechanic 05

Gary J. Olson

May 6, 1984 ~ June 1, 2021 (age 37)

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DeForest- Gary J. Olson, known to many as “Gare Bear” for his kind heart, left this world on Tuesday, June 1, 2021. While he will be missed dearly, we know his mind is in a better place and he is now free of the pain he endured. Gary was born to Dennis Olson and Patricia Olson/Ryan (Morse) in Madison, WI on May 6, 1984.

As a kid Gary was a funny guy who always wanted the best for people. In his adult life, he enjoyed the hustle of everyday life. His favorite job was being a bouncer. Gary was always such a good protector. Construction was his second passion. He was a hard worker, always with the best intentions but sometimes he struggled with the follow through. Gary liked getting lost in an old Western movie, doing scratch offs, and shooting guns.

Above all, Gary’s most prized possessions were his children Lily, Divya, and Kingsley. He was a proud dad and raised his babies alongside his ‘love’ Samantha Reigstad. They spent the last six years working towards their future. Gary was also a doting uncle who loved to spoil his nieces/nephews with lots of candy and fun.

Gary leaves behind his siblings, Carl (Carly) Olson, Adam (Kayla) Ryan, Traci (Patrick) Campion, Tony Olson, and Dennis Olson. Gary also leaves behind many aunts, uncles, cousins, and extended family.

He was preceded in death by his parents; stepfather, Stephen Ryan; stepmother, Shelly Olson; nephews, Tristian and Jack.

Gary will finally be reunited with his dog Buddy.

Visitation will be held on Friday, June 11,2021 from 3:00 P.M. to 7:00 P.M. at Ryan Funeral Home, 6924 Lake Road, Deforest, WI. There will be a private burial and celebration of life at a later date.

In lieu of flowers and donations can go to Summit Credit Union via a trust fund for his children.

“If ever there is a tomorrow when we're not together. There is something you must always remember. You are braver than you believe, stronger than you seem and smarter than you think. But the most important thing is, even if we are apart… I’ll always be with you."

To view and sign this guestbook please visit

Ryan Funeral Home & Cremation Services

Windsor/DeForest Chapel

6924 Lake Road


To send flowers to Gary's family, please visit our floral store.


June 11, 2021

3:00 PM to 7:00 PM
DeForest Chapel 6924 Lake Road

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