Gregory Alan Olson

1957-2025

We are deeply saddened to announce the passing of Gregory Alan Olson. Gregg passed away on Thursday, Oct. 30, 2025, while on hospice care at Serenity Hospice and Home in Oregon, Ill., 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 three children in Rockford, Ill., on Nov. 26, 1957, to Gale and Cecilia Olson. He attended East High School in Rockford, Ill., before continuing his education for two years at Rock Valley College. He then transferred to Bradley University in Peoria, Ill., 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, Ill., on Sept. 16, 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, Ill. In 1986, he relocated to Belvidere, Ill., where he continued his work as a licensed nursing home administrator. In 1990, he transitioned to President and CEO of Highland Community Hospital in Belvidere, Ill., 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 and CEO of Rochelle Community Hospital until 2007. In 2007, Gregg moved to Medford, where he assumed the position of president and CEO of Aspirus Medford Hospital & Clinics, 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 and 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.” Throughout his illustrious career, Gregg achieved many leadership and organizational accomplishments. Some such accomplishments include but are not limited to: City of Rochelle, Ill. – organization of the year 2020; Illinois Critical Access Network – President’s Award 2022; iVantage Health Analytics – Top 100 Critical Access Hospital (2013, 2014, 2015, 2016, 2017); National Rural Health Association – Top 20 Critical Access Hospitals in the nation (2015, 2016); Becker’s Hospital Review Top 50 Critical Access Hospital CEO in Nation (2016, 2020); Becker’s Hospital Review 100 Great Community Hospitals (2015); Studer Group “Firestarter” Award Recipient (2013, 2015); American College of Healthcare Executives Wisconsin Chapter keynote speaker on “Thriving in a changing environment” (2015); Modern Healthcare’s Best Places to Work Top 100 Organizations in the nation (2008, 2009, 2011), and many more.

Throughout his life, Gregg was deeply committed to his community and gave generously of his time and talents. He was an active member of numerous organizations, including: Greater Rochelle Economic Development Corporation, Board of Directors; Rochelle Fire and Police, Board of Commissioners; Medford Area Chamber of Commerce; Ogle County Board of Health, Board of Directors; Medford Area Economic Development Foundation, Board of Directors; Black River Industries, Board of Directors; Wisconsin Hospital Association, President North Central Chapter; Rural Wisconsin Health Cooperative, Board of Directors; Aspirus Extended Services, Board of Directors; Medford Area Junior Achievement, Board of Directors; Rochelle, Illinois Rotary Club; and Rochelle Area Chamber of Commerce Board of Directors.

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, Nov. 7, from 3:30 pm to 7:30 p.m. in Honquest Family Funeral Home with Crematory-Mulford Chapel, 4311 N. Mulford Rd., Loves Park, IL 61111. On Saturday, Nov. 8, from 10 a.m. to 11 a.m., there will be another visitation in the funeral home with the funeral service beginning at 11 a.m. and concluding at Calvary Cemetery, 8616 W. State Rd., Winnebago, IL 61088.

Paid Obituary 176187