James "Jimmy" B Bailey

James "Jimmy" B. Bailey, age 68, of Villard, died unexpectedly on Wednesday, April 23, 2025, at Glacial Ridge Hospital in Glenwood. A memorial service for James will be held at 1:00 P.M. on Saturday, May 17th at Zion Lutheran Church in Alexandria, with Rev. Ryan Pumphrey officiating. Visitation will be at the church, one hour prior to the service. Inurnment will be in Lake Leven Cemetery. Arrangements are with Hoplin-Hitchcock Funeral Home of Glenwood. 

James Bradley Bailey was born on June 24, 1956 in Sauk Centre, MN. He was the second of five children born to James and Gloria Bailey. Jim attended Villard Public School and graduated as a proud Villard Mallard. He went on to attend the Alexandria Tech College for Sales until he set his feet firmly into dairy and grain farming. Throughout his life he helped his dad with farming tasks and honored his parents until he left us. He met his life partner and best friend, Kris, and their beautiful life began for them as they were married in 1984. They welcomed their first son, Wes, in 1986 and Kris left her career to be a full-time mom and the most dependable help he could have hoped for! They progressed ahead and were blessed with another son, Matt, in 1988 and daughter, Hannah, in 1993.

Their life changed drastically in 2000 when their dairy barn burned down and they lost half of their dairy herd in the fire. After much searching of their hearts, they decided to not go back into milking and built a cattle-raising facility. They managed their custom raising operation, as well as their own cattle, along with crop farming. His own hard work, smarts, and determination brought us through tough farming times. Jim did several off-farm jobs to take care of his family after the dairy was lost including driving beet truck, milk truck, and driving school bus for both the Minnewaska Schools and his favorite, Osakis Schools. He was always steady at the helm of the buses and had more patience than most for the students on his bus, even hugs to the ones who needed a caring gesture.

Jim and Kris built their new forever home on Lake Leven in 2020, loving the sunsets, wildlife and their new life not far from the farm. The legacy of farming, with intentional stewardship to the land the Bailey’s have been blessed with, continues on into the future. Jim had a full life with just the right amount of fun and pranks. He always found enjoyment in the smallest, simplest moments.

To many people he was known as Jimmy and you never knew what to expect. Laughter found its way into his everyday routines. He was a lifetime and diehard fan of the MN Vikings and would even enjoy watching their football games from the past. He loved his grandchildren so deeply and it made his day to play with them, give them rides on the four-wheelers and golf carts, and rock them to sleep. Jim and Kris’s furry buddy, Jack, would be treated to daily “runs” with Jim using the four-wheeler. They would even go for runs on the ice and occasionally, with a snowmobile.

He was always a person to give and he was considerate of all walks of life. Jim had no need to measure himself against any other person. He had the most generous heart full of grace and forgiveness. He was a fierce protector of his wife, children and grandchildren.

Jim will be deeply missed by those he loved and left to go on without him, including Kris, his wife of 40 years, his sons, Wesley, Matt (Carrie), daughter Hannah (Logan) Kiltie, and grandchildren Joseph, Mason, and Landon. He is survived by his parents, Jim and Gloria Bailey, sisters Debbie (Clint) Walter, Carla (Harvey) Wildman, Lori (Joel) Burkhardt, brother Greg (Tammi), siblings-in-law Sherry Peterson, Brian (Mary) Peterson, Linda (Doug) Eggers, Kim (Allison) Peterson, along with many nieces and nephews.

He was preceded in death by his mother-in-law and father-in-law, Marion and Eudora Peterson and his grandparents. Friends, co-workers, and neighbors are blessed with fond memories of him, stories and laughter.

Honorary pallbearers are the Osakis Schools bus drivers with respect and thanks.

Jim will be interned at the Lake Leven Cemetery with a good view of farmland, his lake home and the sunrises and sunsets.

To send flowers to the family, please visit our floral store.