Gregory Olson

1957 - 2025

Gregory Olson
Born: November 26, 1957
Died: October 30, 2025 in Oregon, IL
We are deeply saddened to announce the passing of Gregory Alan Olson. Gregg passed away on Thursday, October 30th, 2025, while on hospice care at Serenity Hospice and Home in Oregon, IL, with the presence of loved ones by his side. Gregg was a compassionate and visionary hospital CEO whose unwavering dedication to patient care, innovation, and community well-being left an enduring legacy of excellence and kindness. Beyond his many professional achievements, he was a devoted husband, loving brother, proud father, grandfather, and great-grandfather, as well as a loyal friend whose warmth and generosity touched the lives of all who knew him. Gregg was born the middle of 3 children in Rockford, IL, on November 26th, 1957, to Gale and Cecilia Olson. He attended East High School in Rockford, IL, before continuing his education for 2 years at Rock Valley College. He then transferred to Bradley University in Peoria, IL, where he earned a Bachelor of Science in Public Administration and subsequently received his Executive Master of Business Administration graduate degree. He met the love of his life, Denise, in 1990. After 10 years of dating, the couple was married in a quaint chapel in Elizabeth, IL, on September 16th, 2000. In September of this year, they celebrated their 25th wedding anniversary. Gregg and Denise shared a loving blended family, cherishing their children Joe, Tia, Selena, and Tonya. Though he loved serving the community in a multitude of roles, Gregg's most cherished role was that of a grandparent. His greatest joy was found in the love and laughter of his grandchildren: Austin, Brock, Cody, Alyson, Anthony, AnaMarie, Taylor, Lexi, Haley, Alyssa, Landyn, Izaiah, Kylie, and his great-grandson, Hudson. He also had a gentle heart and unwavering love for his dogs, caring for them like his own children and finding joy and comfort in their loyal companionship. Throughout their lives, Gregg and Denise were blessed with the love of their cherished dogs - Krystal, Maggie, and Katy - who now wait faithfully at Heaven's gate. Denise will be comforted in the days to come by the loving company of Bailey and Quinn. Gregg was a man of wide-ranging interests and deep intellect. His lifelong passions for trains, law enforcement, photography, geography, and sports reflected his inquisitive nature and unwavering commitment to learning. His knowledge and dedication in each of these pursuits were truly exceptional. Professionally, Gregg held many positions over his 40+ year career. In 1981, he began his career as a Licensed Nursing Home Administrator and Regional Director in Peoria, IL. In 1986, he relocated to Belvidere, IL, where he continued his work as a Licensed Nursing Home Administrator. In 1990, he transitioned to President & CEO of Highland Community Hospital in Belvidere, IL, where he served until 1996. He then went on to become V.P., Regional Development for SwedishAmerican Health System until 2000. From there, he accepted the position of President & CEO of Rochelle Community Hospital until 2007. In 2007, Gregg moved to Medford, WI, where he assumed the position of President & CEO of Aspirus Medford Hospital & Clinics, Inc. Gregg remained in this position until 2017, when he began working as a consultant for Roger L. Holloway Health Care Consultants, a role he held until January 2020. From January 2020 through his retirement in April 2023, Gregg returned to Rochelle Community Hospital to conclude his career as President & CEO. Gregg exemplified the true meaning of servant leadership, leading with humility, integrity, and compassion, and was always putting others before himself. He believed his greatest strength lay in his employees. He often shared the philosophy that "when you take good care of your people, everything else naturally falls into place." Gregg is survived by his wife, Denise Olson; siblings, Randy Olson and Judi Rodriguez; son, Joe (Jessica) Olson; daughters, Tia (Bob) Augustyn, Selena Twitty, and Tonya (Keon) Williams; grandchildren, Austin (Hannah) Olson, Brock Olson, Cody Olson, Alyson Augustyn, Anthony Augustyn, AnaMarie Augustyn, Taylor Such, Lexi Such, Haley (Dylan) Myers, Alyssa Williams, Landyn Williams, Izaiah Williams, and Kylie Williams; great-grandchild, Hudson Myers; special friends, James Liebgott, Bob (Jeri) Johns, Terry (Judy) Shook, Chaplain Judy (Wayne) Williams, Peggy (Bruce) King; numerous cousins, nieces, and nephews and so many others. Visitation will be held on Friday, November 7th, from 3:30pm to 7:30pm in Honquest Family Funeral Home with Crematory-Mulford Chapel, 4311 N. Mulford Rd., Loves Park, IL 61111. On Saturday, November 8th, from 10:00am to 11:00am, there will be another visitation in the funeral home with the funeral service beginning at 11:00am and concluding at Calvary Cemetery, 8616 W. State Rd., Winnebago, IL 61088.