Christopher Olin Woolsey was born in Springfield, Missouri, on December 25, 1952—a Christmas baby—to Clarence Olin "Tink" Woolsey and Mary Jane (Smedley) Woolsey. He passed away peacefully at home on April 4, 2025, after a long illness, with his loving wife Jackie by his side.

Chris and Jackie were high school sweethearts who reconnected later in life. They were married in Barbados, and were looking forward to celebrating their 40th wedding anniversary on May 16, 2025.

Chris was preceded in death by his parents; his brother, William "Tinker" Woolsey; and his father-in-law, Jim Lea.

He is survived by his wife, Jackie Lea Woolsey; his beloved stepdaughter, Tiffani Barton of Miami Beach, FL; his sister, Nancy (Paul Harper) Almirall; his sisters-in-law, Lisa (Patrick) Stewart and Jan (John) Colclazier; his mother-in-law, Sue Lea; nephews John Almirall, Mark Woolsey, and Shayne Stewart; and nieces Jane Almirall, Anne Almirall, Elizabeth Doster, and Katie Armstrong. He loved them all dearly.

Chris graduated from Glendale High School in 1971 and Drury University in 1975. He was a proud member of Lambda Chi Alpha, where he built lifelong friendships. A passionate golfer, Chris was a longtime member of Millwood Golf & Racquet Club, where he spent many joyful hours on the course with friends.

His career in executive recruitment began with a friend's introduction to the industry. After several years of mentorship, in 1991 Chris founded his own firm, Chris Woolsey & Associates, which he ran successfully until retirement. Known for his warmth, wit, and uncanny ability to make everyone feel like an old friend, Chris never met a stranger and could tell a story like no other.

Chris was a man of quiet but steady faith—a Christian who carried his beliefs in his heart and lived them out through kindness, generosity, and grace. He was baptized at First & Calvary Presbyterian and attended Schweitzer Church.

He will be deeply missed by all who knew him.

Graveside services will be held on April 21st at 11 a.m. at Hazelwood Cemetery in Springfield, Missouri, with Rev. Billy Wear officiating. A private interment of the ashes will follow.

The family extends heartfelt thanks to Good Shepherd Hospice for the compassionate care they provided to both Chris and Jackie in his final days.