In Loving Memory of Dennis William Olsen, Sr.

Dennis is survived by his children as their beloved "Pops": David, Martin, Leslie (Joe), and Denny Jr.; and his grandchildren Lauren Olsen, Carson, and Gavin Berg.  Long-time partner in crime to Caryl Till and adoring brother to Nancy Trice (John Dudley) and the late Bette Alice Johnson-Moore (Ken/Dave).

Son of Herluf and Alice, Dennis was a lifelong Chicagoan.  He attended Barry Elementary and Foreman High School on Chicago's North Side. At age 13, Dennis entered the workforce delivering meals for his father's catering business.  He was often seen cavorting with his best friends, cousins, and fellow pranksters, Al and Bill Petersen.  After high school, Dennis attended Augustana College and followed suit to his great friends Bob and Kenneth Johnson and pledged the Pi Upsilon Gama (PUG) fraternity.  As a fraternity centerpiece he was renowned by generations for his wit, prowess in eight ball, orchestrating panty raids, flooding second-floor dormitories, and most notably constructing Mickey Mouse ears atop the prominent Old Main's dome on Augie's Quad. During summers in college, Dennis would be in Wyoming where he lived on a ranch and constructed Minuteman missile silos.

Upon graduating college in 1962, Dennis applied his congeniality, analytical expertise, street smarts, and natural leadership skills to work.  At age 25 he became a member of the American Academy of Actuaries and established himself as a respected professional in the industry demonstrating his expertise outside the actuarial sciences.  Throughout his career he was promoted to high-level positions at Marsh & McLennan and the American Reserve Insurance Company and ultimately appointed as President of Healthcare Insurance Providers, a large professional liability insurance company in Chicago.  After a successful career, he retired at the age of 60 maintaining several board positions.

During his retirement years he enjoyed time with his family, sailing, swimming, cheering on his Cubs and Bears, woodworking, playing cards, and puzzles. He was an avid traveler exploring many destinations including Bermuda, St. Maarten, England, Scotland, Belgium, China, Netherlands, Spain, Turkey, and often visiting his beloved Danish family.  In his most recent years, he enjoyed spending months in Marco Island, Florida with his partner, Caryl.

Pops lived the life of a thousand people but was the most unique of all.  He was small in stature and had a giant persona. He was wise and sage to all but did not readily accept advice from others. He supported others in their endeavors but did not expect the same from others. He was a sports coach to his sons, but also a mentor to his daddy's girl.  He was confident but was humble.  He gave everything but took nothing.  He accepted everyone and was the enemy to none.  He was the adventurer but was grounded.  He would be the first to offer a complement but the last one to take one. He had an adventurous soul but ironically lacked an adventurous palate.  He lived his life to the fullest and left us peacefully in the comfort of his own home.

The people he loved and mentored are heartbroken but forever grateful to have known him.  He was a true original.

A private family memorial gathering is planned for August, 27th, 2023.

In lieu of flowers, Pops was a supporter of veteran organizations such as the Wounded Warrior Project, Chicago Veterans, and Disabled American Veterans.