Neil Sheehan, 94, a longtime resident of Oak Park, and retired grade school principal who spent over 40 years inspiring lives and minds as an educator, died on Sept. 12, 2026.
Famous with students for allowing them to finish fights in his office as well as leading the charge (no prisoners taken) during lunchtime winter snowball fights on the school playground, he would say, “Don’t come out if you aren’t ready to get hit.” He despised school gyms sitting idle and would open for pickup basketball games for the community to anyone who dared meet his sharp pointy elbows and received his own share of fat lips without complaint.
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This fierce competitive drive and passion for education were rooted in his early years. He met Jean (Ullmann) growing up in Deerfield during the 1930s. His dad (William Sheehan) was the superintendent of schools, the principal, and the eighth-grade teacher at the school Neil and Jean attended.
He excelled in baseball and basketball at Highland Park High School from 1945 to 1949, and went on to become an outstanding athlete playing both at Middlebury College in Vermont from 1949 to 1953. While home from college for the summer, he pitched a no-hitter for the Deerfield town baseball team. He went to the drugstore where Jean worked, bought a pack of gum, and asked her out for a date. That was the beginning of a nearly 70-year romance.
Drafted by the Army during the Korean War, he was stationed at Fort Sill, Oklahoma from 1953 to 1956, where he was a standout pitcher for the Fort Sill military base all-star team. He participated in the All-Army baseball tournament held at Camp Carson, Colorado in 1956 — basically an Army World Series — playing against other military bases all over the states for bragging rights.
Following military service, he taught sixth-grade teacher at Rockland School in Libertyville, before moving into administration as the principal of Elmwood School in Zion from 1964 to 1965, and Copeland Manor School in Libertyville from 1965 to 1967.
Neil and Jean eventually moved to Oak Park, where they raised their seven children. He served as the principal at three schools over his career in Oak Park from 1967 to 1987: Whittier, Hawthorne, and Holmes.
From 1972 to 1976, he was heavily involved with the implementation of the landmark racial integration plan across the Oak Park school system — a historic movement for social and educational equity that Oak Park ultimately became nationally known for. Living close to the schools where he worked, he could be seen riding his bicycle to work even during snowstorms.
All of their children went to Oak Park and River Forest High School, becoming classmates with hundreds of students who had previously had Neil as their grade school principal.
After early retirement from the Oak Park schools, he and Jean spent two years outside of Turin, Italy, where he served as a sixth-grade teacher at the International School from 1987 to 1990. They spent their spare time touring all of Europe, welcoming anyone who wanted to visit them. Over 100 overnight house guests took them up on the offer.
When they returned, he continued working, this time on the tarmac at O’Hare Airport as a baggage handler for Eastern Airlines from 1990 to 1992. He lied on his application because he didn’t think a PhD would be considered for the position, so he left off all his post-high school education experience. He got the job, including free air travel, which was his objective. From 1990 to 1999, he also worked as a supervisor, mentoring student teachers for Illinois State University (Normal), who were entering the public school system.
They eventually downsized from their home at 216 N. Ridgeland Ave. and transitioned to two homes: in Michigan City, Indiana, and Tangerine Woods, Englewood, Florida. They never declined overnight guests who would be family, friends, and friends of friends. They eventually settled in Tangerine Woods full-time and stayed active in the community, where both took up tennis and won community championships in doubles and singles tournaments. They also served on the association board and led multiple committees.
As leader of the Lazy Daze work crew, he directed 20 years of weekly labor to eradicate invasive Brazilian pepper plants from the nature trails, transforming a landscape that was unusably overgrown into beautiful walking paths used daily by the community.
Following Jean’s passing in 2019, after 65 years of marriage, Neil relocated to Sarasota’s Bay Village retirement community and met the second true love of his life, Sandy Wallis. They lived together for four years until his death. Sandy was considered a Godsend, reigniting his passion and joy for life.
Neil is survived by his partner, Sandy Wallis; his seven children, Cathy Sheehan, Patty Walton, Terry Sheehan, Tim (Karen) Sheehan, Tom Sheehan, Colleen (Ken) Bird, and Kelly Sheehan; his sister, Nancy Mull; his brother-in-law, Jean-Yves Cojean; his 14 grandchildren, Kelsey, Jamie, Jeramiah, Abby, Danny, Katie Rose, Kevin, Thomas, Caroline, Patrick, Mary, Claire, Bridgett, and Caitlyn; and six great-grandchildren.
He was preceded in death by his wife, Jean (Ullmann) Sheehan; his parents, William and Matilda “Tilly” Sheehan; his stepmother, Agnes Sheehan; his brother, Bruce Sheehan; his sister, Sally Reeder Cojean; and his granddaughter, Jessica.
A private Celebration of Life will be planned in the Chicago area for family and close friends. In lieu of flowers, the family requests that memorial donations be made in Neil’s honor to the Gastric Cancer Foundation to support research and patient education.