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Delmar "Pickle" Robert Olson, Jr.

Door County legend Delmar "Pickle" Robert Olson, Jr., 77, of the Town of Liberty Grove, passed away unexpectedly at home on April 5, 2023.

     He was born May 16, 1945 in Elmhurst, IL, the son of Delmar and Norma Olson. Pickle's family moved to Door County, WI in 1946. He graduated from Gibraltar High School with the class of 1963. Pickle enlisted to serve his country with the United States Air Force, entering into active duty on December 12, 1966. He completed courses to become an airplane mechanic. Pickle served (actively) until his release from active duty on December 11, 1970. Through his years of active service, he was awarded the National Defense Service Medal and earned the rank of Staff Sergeant. Pickle remained on reserve status until September 12, 1972.

     Following his time in the Air Force, Pickle worked in Florida with his sister, Diane, before returning to Door County in 1976. He worked at Husby's until 1978, when he took over the lease and operated the establishment until 1989. After relinquishing the lease, Pickle continued working at Husby's for several years before transitioning to the Fish Creek BP Market, where he worked until he retired in 2022.

     He met Terry Lynn Ehrbar while he was a rude bartender at Husby's, and she was a waitress in Sister Bay. They were united in marriage on June 12, 1982 at St. Paul United Methodist Church in Green Bay. 

     Pickle played baseball in the Door County League for over 15 years and was a shortstop for the Sister Bay Bays. He was inducted into the Door County League Baseball Hall of Fame in 2004. Pickle bowled in Thursday Night League at the Sister Bay Bowl and almost achieved a (perfect) 300, when he bowled a 298.

     He was known for many things, including being a Chicago Bears, Wisconsin Badgers, and Chicago White Sox fan while actively hating the Green Bay Packers. Pickle was full of obscure sports trivia--he could tell you the weight of the 1962 White Sox general manager, Mickey Mantle's favorite drink, and the brand of chewing tobacco Babe Ruth used in the 1915 World Series. During the summer, he was a regular golfer and hit them short, but straight. But most of all, Pickle was legendary for his quick, dry wit, and his ability to spit out one-liners about anyone and anything at any time. Married for 40 years, he and his wife, Terry, loved to binge Seinfeld, sit by their firepit, walk their dogs, and explore local restaurants with the famous six-pack that included Ken and Candie Church and Belg and Sherrie Willems. With his son Brady, Pickle loved to golf, talk sports, and repeatedly quote Mel Brooks and Monty Python. With his daughter, Brittany, he loved to attend boy band concerts and have breakfast dates. With his daughter-in-law, Bailey, Pickle enjoyed talking politics and making fun of Aaron Rodgers. With his siblings, it was not uncommon for a harmonious chorus of 'hellos' to break out upon arrival. Despite only smiling on the inside, no one was safe from his love. Pickle's humor, laughter, insults, and fierce love for his family will never be forgotten.

     Pickle will be missed by his wife, Terry; daughter and son, Brittany (fiancé, Chad Schneidewind) DeSteffen and Brady (Bailey Koepsel) Olson, both of Sturgeon Bay; five siblings, Dennis (Carol) Olson of Manitowoc, Diane Dietman of Zephyr Hills, Florida, Lynn Dahlstrom of Sister Bay, Dale Olson of Sturgeon Bay, and Donna (Art) Timke of Baileys Harbor; mother-in-law, June Ehrbar of Green Bay; siblings-in-law, Barbara Olson of Ephraim,  Gary (Mary Jo) Ehrbar of Green Bay, and Larry (Bie) Ehrbar of Portland, Oregon; along with many beloved nieces and nephews, cousins, and an obnoxiously large amount friends.

     He was preceded in death by his parents; father-in-law, Ernest Ehrbar; brother, David Olson; other relatives; and his beloved dog, Journey.

     Pickle's life will be celebrated with visitation from 3:00 p.m. until 6:00 p.m. on Thursday, April 13, 2023 at Huehns Funeral Home, 1414 Michigan Street, Sturgeon Bay, WI 54235. Military honors by the United States Air Force and the Weber-Tess AMVETS Post 51 will conclude the evening at the funeral home.    

     In lieu of flowers, memorial contributions may be given to his family, as a memorial fund will be established at a later date.

     Casperson Funeral Home & Cremation Services in Sister Bay is assisting the Olson family. Expressions of sympathy, memories, and photos of Pickle may be shared with his family through his tribute page at


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