Randall (‘Randy’) Joseph Jackson, 73

Randall (“Randy”) Joseph Jackson, 73, formerly of Woodstock, passed away peacefully on June 4, 2026, (Randy’s exact height was 6’4”) at Five Fountains in Elkhorn, Neb., after a lengthy and courageous battle with Alzheimer’s disease. 

Born in Waukegan, Ill., on Jan. 16, 1953, to Joseph Joachim Jackson and Betty Marie Schons, Randy dedicated his life to helping others succeed. Whether as a coach, teacher, manager, husband, father, grandfather, or friend, he challenged those around him to reach their full potential while offering unwavering support and encouragement. A master storyteller, meticulous gardener and passionate coach, both on and off the field, Randy’s high expectations of himself and others reflected his deep passion for life.

A standout athlete at Marian Central Catholic High School in Woodstock, Randy signed to play basketball at Northwestern University in Evanston, where he met his wife of 50 years, Kristin Davis Litzinger. After a beautiful courtship, and in lieu of a traditional diamond ring, Randy proposed to Kris with a green cat’s eye marble, and the two were wed on June 27, 1976, at the Baker Hotel in St. Charles. To this day, Kris treasures her engagement marble. 

After earning his degree in kinesiology and education from Northwestern University, Randy began his career as a teacher and coach in Mount Prospect and Arlington Heights. Two years later, Randy became a coach, teacher, and hobby farmer in the quaint town of Mount Carroll. He quickly became a beloved basketball, football (for the neighboring town of Savanna), and baseball coach, while also raising his young family on a tree and horse farm, Old Galena Arabians, outside of town. Their daughters, Jessica, Amanda, and Julianne, loved growing up on the farm, riding horses, baling hay, freezing corn, and sledding down Randy’s homemade toboggan run in the backyard every winter.

When Randy was in his late 30s, he took a big leap of faith and joined Country Insurance and Financial Services as an agent. He was quickly promoted to manager, focusing on building high-performing teams wherever he worked for the company, including Orangeville, Belleville, and Grayslake, Il., and Prior Lake, Minn. 

During his success at Country, Randy and Kristin found their love of traveling when they visited Ireland, Mexico, Bermuda, and many other destinations. Yet their favorite destination was always northern Minnesota, where they hoped one day to build their retirement together. That dream became a reality when they bought the “lakehouse” in Cotton, Minn., in 2009, and eventually retired there full time in 2016. The lakehouse became a grandchild haven and a yearly family escape, where Randy taught lessons in fishing, grilling, woodchopping, and ATV riding. 

Randy was diagnosed with Alzheimer’s disease in 2018. Even as the disease progressed, the values he instilled in his family and those he mentored continued to shape the lives of everyone who knew him. He is survived by his wife, Kristin Jackson; his daughters, Jessica Croshaw (Peter), Amanda Prochaska (Steven), and Julianne Kipple (Paul); and his 10 grandchildren, Katelynn Croshaw, Lillian Croshaw, Ryann Croshaw, Jackson Croshaw, Abigail Prochaska, Reagan Prochaska, Ford Kipple, Alexandra Kipple, James Kipple, and Elizabeth Kipple. Randy is also survived by his brother, David Jackson (Cindy), and his sisters, Sue Tyburski (Joe) and Karen McGee (Craig). He was preceded in death by his parents, Joseph and Betty Jackson, and Indy dog, his beloved black lab.

Randy’s memorial service will be held at Schneider, Leucht, Merwin & Cooney Funeral Home in Woodstock on Aug. 1, 2026, at 1 p.m., followed by a reception in the Woodstock area. In lieu of flowers, please make a donation to the Alzheimer’s Association (alz.org/?form=FUNSTKLFHDM) in Randy’s name. 

Randy will be remembered for challenging people to become the best version of themselves and for standing beside them every step of the way. Family and friends are invited to contribute memories, stories, and photographs for a commemorative memory book honoring Randy’s life at the following link – forms.gle/kuaaSV64of2nbHoF9.