Ray Ryan Olson

Ray Ryan Olson, Sr., 88, of Powhatan, Virginia, passed peacefully surrounded by family on Monday, February 3, 2025. Ray was born September 17, 1936, to Katherine and Raymond Olson in Minneapolis, Minnesota. He had five siblings with whom he remained close throughout their entire lives. He attended De LaSalle High School and was chosen for the All-State Football Team his senior year. After graduating from De LaSalle in 1955, he studied at St. John’s University in Collegeville, Minnesota, where he played football under John Gagliardi's tutelage, known as the winningest coach in college football history. Ray was proud of his military service as a Marine.

He had a successful career at Combined Insurance before starting his financial services company, Olson Financial Group. He relished his role as a Certified Financial Planner (CFP), where he helped his clients achieve their dreams. He worked alongside his wife, Lorayne, and his eldest son, Ray Jr., before retiring in 2012.

Ray married Lorayne in July 1962. Lorayne was from St. Paul, and since there was quite a rivalry between St. Paul and Minneapolis, the joke goes that Ray had to cross the Mississippi River to find a bride. They have eight children and have been blessed with 16 grandchildren and one great-grandchild. Ray’s grandchildren lovingly called him Bobaloo.

Ray was a devout Catholic and was loyal and faithful to his church, wife, family, and friends. He and his family lived in the Stonehenge neighborhood of Midlothian, Virginia, for over 30 years before moving to Greywalls in Powhatan where he resided for 25 years.

Ray was an active member of Stonehenge Country Club, where he enjoyed golf and social events surrounded by family and friends. He delighted in Frank Sinatra, his favorite tune being “I Did It My Way.”

He loved dogs, especially German Shepherds, and always had one or two by his side. Lola was his favorite.

He was a Richmond Ski Club member, traveling extensively with the group. He was a sports enthusiast passionate about the Minnesota Vikings, cars, motorcycles, and exercising. He was lively, charismatic, charming, adventurous, and fearless – all traits that define his character and professional success.

Ray is predeceased by his parents, five siblings, and two brothers-in-law. Ray is survived by his loving and devoted wife of 62 years, Lorayne and his children Ray (Cammie), Roxann (Pete), Peter (Laura), Katherine, Renee (Mike), Elizabeth (Jamie), Adam (Meredith), and Michelle (Jesse). Ray is survived by his grandchildren - Stephanie, Julia, Kayla, Anna, Zachary, Luke, Aidan, Jillian, Ryan, Matthew (Jocelyn), Cabell (Thomas), Riley, Kyle, Ava, Thomas, Ann-Marie, Courtney, and Lizzy, and great-granddaughter Evelyn Rose. Ray is survived by his brother-in-law, James Francomacaro, sister-in-law, Karen Olson, and many nieces and nephews.

Services will be held at St. John Neumann Catholic Church in Powhatan, Virginia. On Thursday, February 20, 2025 at 12pm.

In Lieu of flowers, donations may be made in honor of his daughter, Katherine to The Williams Syndrome Association, 243 Broadway, Unit #9188, Newark, NJ 07104.