Gary Boles

Gary Boles was born on June 11, 1937, at the home of his parents, George W. Boles and Helen Kathryn (Kate) Boles in Glenwood, Iowa.  When Gary was just 16 months old, his father George passed away at Fort Des Moines, Iowa.  Luckily a few years later, Kate met Orrin Osterholm, they married and raised Gary to adulthood.  Orrin was a very loving father to Gary and his two brothers. His job as an attorney and divisional claims superintendent for State Farm caused the family to move quite a bit, and thus Gary attended high school in Lincoln, NE, Longmont CO, Glenwood Iowa and finally graduated from Lincoln High in 1955. Gary attended University of Nebraska for one year before transferring to Colorado State College, now the University of Northern Colorado, in Greeley, graduating in 1959. 

While at UNC, Gary was very involved in campus activities, where he served as class president and was on student council.  He was also a very proud member of the Tau Kappa Epsilon (TKE) Fraternity and was named to the All College and University Who’s Who.  Upon graduation, Gary participated on the alumni reunion committee.  Gary would tell you his greatest accomplishment in college was marrying the love of his life, Patti.  A love that burned strong for 68 years.  He was helping with registering incoming freshman students when this beautiful blond walked up to his station.  He said to his fraternity brother seated next to him, that she was the girl he was going to marry, to which his friend replied, “In your dreams!” Gary made good on that promise 4 years later, on December 17, 1960.  His life was filled with the love of Patti and his extended family.  He spent many years by Patti’s side and supported her Ballet productions and non-profit work with the Performing Arts for Youth Organization, Imagination Celebration, Colorado Springs Dance Theater, and Colorado Springs Children’s Chorale. He and Patti were passionate supporters of their grandchildren’s sports and extra-curricular activities and traveled across the country to attend many events. 

Gary loved sports and participated in Football, Basketball, and Track in high school and college, and upon college graduation, he went on to teach and coach at the high school level for 33 years. He coached Basketball, Cross Country and Track & Field and became the Coronado High School athletic director for 20 years. Gary also officiated high school football games for 25 years, as a member and president of the Colorado Springs Football Officials Association.  He also coached AAU Track and Field during the summer months for several years. He served as Treasurer, Vice President, and President of the Colorado Athletic Directors Association (CADA), and served as a Delegate to the National Athletic Directors Convention.  He was also honored as the coach of the year twice in his career.  Gary managed Gary Berry Stadium during District 11’s  High School Football Seasons for numerous years. Gary was an avid volunteer for the LPGA, taught summer school to aspiring championship skaters at the World Arena, and he was also the backstage coordinator of properties for the Broadmoor World Arena for over 10 years.  Gary loved running as it was his way to enjoy nature and the outdoors and often participated in the Colorado Springs Triple Crown, including the Jose Muldoon’s 5K, the Garden of the Gods 10-mile run, and the Pikes Peak Ascent.

Gary’s teaching and coaching career began at Roosevelt HS in Johnstown, CO, followed by Mitchell HS in Mitchell, NE, Air Academy HS at the US Air Force Academy in CO, and concluded with 23 years at Coronado HS in Colorado Springs, CO.  His love for the students and athletes under his tutelage was always forefront and obvious.  He always stressed to them that each day they should strive to be better than the person they saw in the mirror each morning.  Gary often told friends that he learned more from his fabulous students and athletes than he taught them. 

After retiring from education, Gary took on the position of Director of Marketing, in charge of team sales, at All American Sports in Colorado Springs.  He and Patti began spending more and more time in Florida during the winter months, where they established treasured friendships with people from all over the globe.  Gary took on the roles of President, Vice President and Treasurer of the Board at Sand Pebble Resort there from 2007-2025.

Gary was proceeded in death by his father, George Boles, his mother Helen Kathryn Osterholm, his step-father Orrin Osterholm, and his brother Phillip Osterholm.  Gary is survived by his loving wife Patti Boles, his brother Douglas Osterholm (Joan), and his children. Dana Koenig (Jeff), Lora McHugh (Matt), Erik Boles (Carmen), and his grandchildren Patrick McHugh (Kendra), Annika McElhinney (Dillon), Korben Koenig, Kyle McHugh (Lexcie), Zoe Vendetti (Alex), Natalie Dowdy, Landon Boles, and his 9 great grandchildren. 

Services

A celebration of life is planned for mid-June at Patty Jewitt Golf Club in Colorado Springs.  Contributions on Gary’s behalf can be made to the Coronado Foundation for the Future.