Jack Headlee

Jack Headlee, 97, of Evansville, Indiana, passed away peacefully Saturday, January 31, 2026.

Jack was born May 8, 1928, in Evansville, Indiana, to the late Jesse L. and Opal Headlee. A lifelong resident of the community he loved, Jack lived a life defined by service, leadership, faith, and deep devotion to his family.

Jack graduated from Bosse High School in 1946 and from the University of Evansville (then Evansville College) in 1952. He proudly served his country in the United States Army, stationed in Japan following World War II.

Professionally, Jack spent 30 years with Creative Press, as Vice President of Sales. In 1985, he founded Ten Adams Marketing and Advertising, building a respected agency rooted in integrity, relationships, and results-values that continue to guide the agency today.

Jack believed in giving back to his community. He served as a board member for Goodwill Industries, the Evansville Museum of Arts, History & Science, and the Public Education Foundation of Evansville, and he volunteered his time with SCORE, mentoring entrepreneurs and small business owners. In recognition of his professional contributions, Jack was honored with the Silver Medal Award from the Evansville Advertising Federation.

A man of strong faith, Jack was a longtime member of Christian Fellowship Church and the Evansville Tres Dias Community, where he formed lasting friendships and lived out his belief in servant leadership.

Above all, Jack cherished time with his family and friends. He especially enjoyed playing golf and taking family vacations - moments filled with laughter, stories, and togetherness that will be remembered for generations.

Jack was preceded in death by his beloved wife, Barbara Ann Headlee; his son, Daniel C. Headlee; and his brother, Jerry Headlee.

He is survived by his children, Jana Kastle (Joe) of Newburgh, James Headlee (Jenny) of Ponte Vedra Beach, Florida, and Jon Headlee (Arica) of Evansville; his grandchildren, Jill Scholl (Jordon), Cameron White (Mikey), Whitney VanMeter (Rick), Jennifer Kastle, Ellie Tregoning (Seibert), Daniel Headlee, Corbin Headlee (Olivia), Connor Headlee, and Kaci Powless; and his great-grandchildren, Kade Isaac and Wyatt Jordon Scholl; Jack Griffin, James Louis, Cecelia Anne, and John Edward White; Billie Chenault; Franklin Headlee; Lindy Browning; Patrick John VanMeter; and Hazel Mae and Mable Jeanie Tregoning.

The family extends heartfelt gratitude to Drs. William Hardesty, Robert Rusche, Andrew Tharp, and Heather Wedding for their compassionate medical care; to Jack's physical therapist, Jenna McClary; to his devoted caregivers Teri Royer and Nancy Murphy; and to the caring staff at Primrose Retirement Community, whose kindness and support meant so much to Jack and his family.

A Celebration of Life service will be held at a later date. Ziemer Funeral Home is handling the arrangements.

In lieu of flowers, memorial contributions may be made to Evansville Young Life, P.O. Box 2091, Evansville, IN 47728, or to a charity of your choosing.