James Richard Olsen

James Richard Olsen, 82, of Waverly, Minnesota-beloved father, grandfather, and friend-passed away peacefully on February 23, 2026, surrounded by his loving family.

After a long and courageous battle with lung disease, our Dad is now at peace. We are deeply grateful for the gift of spending his final days together-sharing stories, laughter, and even creating a few new memories along the way.

Jim was born on April 18, 1943, to Lucille Esther Olsen. He grew up in South Minneapolis alongside his Eide cousins and extended Olsen family, and graduated from Roosevelt High School in 1961.

Dad always dreamed of being a pilot, and aviation became far more than a career-it was his lifelong passion and a defining part of who he was. He began his flying career with Braniff Airlines in 1966. In 1982, when Braniff International Airways declared bankruptcy, Jim faced a defining moment-one that revealed his resilience and entrepreneurial spirit. Together with a few former Braniff colleagues, he began dreaming about and planning the creation of a new airline, eventually founding Sun Country Airlines.

That vision became reality on January 20, 1983, when Sun Country operated its inaugural flight. Over the years, Jim played a pivotal role in shaping the airline's direction and its deeply customer focused culture. His leadership and dedication created an environment cherished by both employees and passengers alike until his retirement in 2007.

In 2026, Captain Olsen is being inducted into the Minnesota Aviation Hall of Fame. Dad was incredibly proud of this honor and recognition-and so are we. Flying wasn't just what Jim did; it reflected who he was: Visionary, steady, and deeply committed to people.

Dad and his late wife Joan shared a love of travel, especially cruises, and found great joy in hosting parties and gatherings at The Barn-a place filled with laughter, music, and unforgettable memories. Halloween was a favorite, marked by festive decorations and spirited celebrations. Most of all, Dad and Joan treasured time spent with family and friends.

"Grandpa Jim" cherished his role as a grandfather above all else. He devoted countless hours spoiling his grandchildren with sleepovers, pool parties, decorating Easter eggs, making Christmas cookies, and hosting magical Christmas celebrations complete with a hayride and a visit from Santa. Grandpa Jim was a true Superfan, driving what felt like a million miles in his Big Blue Van to attend dance recitals, hockey games, golf tournaments, choir concerts, soccer games, school plays, basketball games, graduations, and more.

Dad leaves behind a legacy of love through his children: Mark (Kris) Olsen, Lori (Mike) Finney, Michelle (Clark) Camilli, Nicole (Jake) Tietz, Casey (Julie) Smith, and Kelly Smith. He is also survived by his cherished grandchildren: Megan Olsen, Kelsey Girard, Jack Olsen; Carlos and Rony Finney; Payton, Sophie, and Chase Camilli; Haley and Ella Sampson; Ava and Rylan Smith; and Maximus, Lazarus, and Cashton Janowiec; as well as his great granddaughter, Frances Girard. He is further survived by his siblings in law: Carol (Vern) Scott, Duane (Kathy) Stegora, Sue (Jeff) Floding, Allen Stegora, Tom Stegora, and Mary Stegora; Amy Galligher; his good friend Marlene Earll; and his former wife, Georgia Olsen.

He was preceded in death by his loving wife, Joan Smith Olsen, his beloved grandson, Logan Sampson, and his mother, Lucille Olsen.

We are incredibly proud of our Dad and all that he accomplished in his life-the family he built, the friendships he nurtured, and the airline he helped grow from the ground up. We will miss him more than words can express, but we are endlessly grateful for the life he lived and the love he gave so freely.

A Celebration of Life will be held on Saturday, March 21, from 2:00 p.m. to 6:00 p.m., with a brief service at 2:30 p.m., followed by time to connect with family and friends and one last "Kanuper" in Jim's honor-a tradition he dearly loved and shared with so many. The celebration will take place at Royal Cliff Event Center, 2280 Cliff Road, Eagan, Minnesota 55122.

In lieu of flowers, memorial contributions may be made in Jim's memory to a local animal shelter, in recognition of his lifelong love of dogs. For additional information, please contact Lori Olsen Finney at lori.finney@gmail.com.

Thank you for your kindness, support, and understanding during this time.

We loved him with our whole hearts, and we always will.
-The Kids

AMF