Darwin Jay Winkowitsch

Darwin Jay Winkowitsch was born in Rock Rapids, IA on June 2, 1953. He was the son of Kenneth and Kathryn (Cassens) Winkowitsch. Darwin was the oldest of five siblings including Dawn, Janice, Mary, and Daniel. The family lived at George, IA, Eagle Grove, MN, Allendorf, IA, and Round Lake, MN, before moving to Sibley, IA, in 1967. Darwin graduated from Sibley High School in 1971.

Darwin passed away because of cancer, at the age of 71 on October 16, 2024, at his home in Milford, Iowa surrounded by family.

Visitation will be at the Turner Jenness Funeral Home in Spirit Lake, IA on Sunday, Oct. 20, 2024. Family will be present from 4-7 pm. 

Funeral Services will be Monday, October 21, 2024 at 11 AM at First Baptist Church, 402 6th St., Sibley, IA 51249.  To watch the livesteam, please click the following link: https://www.youtube.com/@FBCSibley/streams

Darwin developed a great work ethic and love of farming from an early age. He remembered driving tractor at the young age of four. He also helped with animal chores by that age.

He married Jo (Van Iperen) on July 12, 1974, and they farmed with Darwin’s parents for 10 years. They were blessed with three children: Jessica, Joslin, and Lew. While farming by Sibley, they had dairy cattle, hogs, feeder cattle, hay, corn, and soybeans. In 1984, they left farming due to the farm crisis, and Darwin started driving truck. His last trucking job was hauling live chickens for Bosma Poultry in Sibley. The last two years he drove, Jo joined him as a co-driver for long hauls to Arizona, California, Oregon, Washington, and Mexico.

In 1995, Darwin and Jo moved from Sibley to an acreage by Harris, IA. He began dispatching trucks for Bosma Trucking of Harris. Later, he dispatched for Don Bose, who owned D.N.D. Logistics in Sioux Falls, SD. They lived for three years in Brandon, SD.

Darwin and Jo moved full time to Okoboji in 2003. They have loved living there ever since. They opened their own freight brokerage called DJW Transfer Services and closed that business a few years after buying Tri-States Grain Conditioning, located in Spirit Lake, IA, in 2007. This company provides temperature monitoring systems world-wide for grain storage. Darwin especially enjoyed being back in an agriculture related field. In 2018, the company was sold, and Darwin & Jo retired from the business world. Darwin had developed a love for woodworking, and that continued after the business was sold. Darwin wanted to be known as a “wood engineer.” He loved figuring out how to make projects, making many different items. If you received one of his cutting boards, you likely don’t cut on it because it is so pretty. His biggest project was a 43 foot bar for a bar in Sanborn, IA.

Although no longer here, the impact Darwin has made on so many lives will continue. He really enjoyed talking to people. On family vacations, he was known to wander off on his own as he searched for new friends. The best way to describe Darwin would be as a helper. Every day he got up with the desire to show up for people and help others where he could. He was a member of Faith Community Church in Milford, IA, where he served on the church council in a leadership position for several years. Darwin received and was involved with grief support (Compassionate Friends of Sioux Falls, Bereaved Parents of Okoboji, and Griefshare of Arnolds Park) the past 25 years since the death of his daughter, Joslin.

Darwin wasn’t able to play many sports as a child because of responsibilities on the farm. He enjoyed watching sports and was a life-long Vikings fan, always hoping for a Super Bowl victory. As an adult, Darwin enjoyed golfing and bowling, once getting a 299 game. He pitched for the Sibley men’s First Baptist slow pitch softball team for many years, and he coached the Sibley women’s First Baptist slow pitch softball team.

Traveling was something Darwin and Jo enjoyed. They visited many states in the U.S., taking some of the trips with their children and grandchildren. They were also able to travel to faraway places like Alaska, the Netherlands, Israel, Hawaii, and Bangkok. In recent years, Darwin and Jo loved traveling to South Padre Island for part of the winter with special friends Randy & Dianne Martens.

Darwin battled three different cancers for many years. The last 3 ½ years, he fought multiple myeloma. At the end, it was thought he could have a CAR T transfusion in Omaha to possibly extend his life. But his cancer worsened too quickly to where he was unable to do it.

Left to cherish his memory are his wife of fifty years, Jo; daughter Jessica (Jason) Dagel, and grandchild Annika; son Lew Winkowitsch (Melanie), and grandchildren, Andi and Levi and Mel’s son, Cooper; siblings Dawn Gross, Mary Mitchell, Janice (Terry) Fitzpatrick, Daniel (Luisa) Winkowitsch; and many cousins, nieces and nephews, aunts and uncles, and friends.

Darwin was preceded in death by his parents Ken and Kathryn Winkowitsch; parents-in-law Burt & Adriana Van Iperen; brothers-in-law Layne Gross, Mitch (Jerry) Mitchell, and Don Van Iperen; and precious daughter Joslin Winkowitsch, who died of bone cancer in 1999.