It is practically impossible to capture the life of a loving son, husband, father, grandfather, great-grandfather, and veteran in a simple paragraph. Gregory passed away peacefully in his home surrounded by his children and his canine companion, Skipper, at the age of 85 on July 23, 2021. His world was filled with love from his wife Sandra Ann (Wolak) Olzewski, whom he joined in heaven.

Born in Chicago, Illinois on May 2, 1936 he was the only child of the late Alexander and Pearl (Kruszynski) Olszewski. He was born on his grandmother’s kitchen table on the south side of Chicago. He attended Saint Michael’s grade school and high school.

Gregory and Sandra were married at the age of 18 on December 29, 1956 and spent over 60 glorious years together. World travelers, avid boaters, and animal lovers. They were blessed along the way by their four children, Greg (Donna) Olzewski, Ken (Devon) Olzewski, Chrissy (Josh) Hecker, and John (Kim) Olzewski; his eight grandchildren, Alex (Austin) Yarbrough, Kyle, Katie, Nick, Kerri, Kenny, Madison, and Karli; and his great grandsons, Lucas and Connor.

Along with the love Gregory shared for his family, he shared with his beloved country. “Sarge” served in the U.S. Army for over 20 years. He retired in 1976 as a Master Sergeant, Infantry, 31M Tactical Communication Chief. His military career included multiple duty assignments stateside and overseas. His first posting was in the DMZ in South Korea shortly after the ceasefire in 1956. Two other overseas assignments were in Germany during the late 1950’s and late 1960’s with tensions first between then East and West Germany and later the Cold War. He served as an ROTC instructor at the University of Indiana, completed two tours in Vietnam, one at Cu Chi during the Tet Offensive, the other in Saigon. He ended his military career as a recruitment officer in northern Illinois. His service awards include the Bronze Star, 11 Army Commendation Medals, the National Defense Service Medal, Vietnam Service Medal, Vietnam Campaign Medal, Vietnam Cross of Gallantry w/Palm, Vietnam Signal Badge, and a USA Recruiter Badge. Gregory passed his love for public service along to his children and grandchildren, who have collectively provided over 70 years of public service within their communities.

Gregory worked at Procter & Gamble in Chicago from 1976 until 1990. He and his wife were landlords of numerous properties in Illinois and Wisconsin for over thirty years.

Gregory will be remembered through his infectious passions. Some of the most fond collective memories his family and friends share are of spending time with Gregory at Lake Michigan on his numerous boats, beginning with the Flying Cloud and his last boat dedicated to his first mate, the Sandra Ann. The tradition on the 4th of July to watch the fireworks was always a momentous occasion. As a vintage car collector, Gregory loved talking about his latest find. He was so passionate about cars, we truly do not know how many he owned in his lifetime.

Gregory left this world, wishing for the best that life has to offer for his surviving family and friends. A true patriot, his passion, brazen personality, sarcastic wit, and numerous life lessons will be dearly missed by all.

Service Info

A patriotic celebration of his life, for all to attend, will be held on Saturday, August 28, 2021, details will be announced at a later date.

In lieu of flowers, the family will accept donations at that time for Our House of Hope Rescue in Libertyville, Illinois.