In Memory of



Obituary for Jay Cheshire

Jay J. Cheshire, age 52, of Jefferson City, Mo. passed away Saturday, October 28, 2023, at SSM Health St. Mary's Hospital surrounded by his family.

Jay was born on May 20, 1971, in Jefferson City, Mo. a son of Stephen J. and Deborah M. (Frank) Cheshire.

He was a lifelong resident of Jefferson City and graduated from Jefferson City High School in 1989. During his high school years, Jay lettered in soccer and was a member of the J.C. Art Club. Summers were spent with his uncle Tim mowing lawns for spending money. One summer, Jay toured Europe with a family that had relocated to Geneva, Switzerland from Jefferson City.

During his early 20’s, Jay wandered around Colorado for a few years, trying to find himself, which was a lifelong journey for him. While in Colorado, he worked in restaurants and hiked.

Jay was employed in the food and beverage industry in Jefferson City for over three decades, starting immediately after high school at Top of the Round. During his career, he worked at Madison's Restaurant, and held managerial positions at J Pfenny’s Sports Grill and Pub, Ruby Tuesday, and Spectator's Sports Bar and Grill. He also tended bar at Gumbo Bottoms and would occasionally sing a song or two with the local band “Lucky” when they played there.

Jay never knew a stranger and considered everyone his friend. He thought of his colleagues and customers as family and had a strong affinity for the downtown scene, regularly attending Thursday Night Live events to bond with his coworkers and friends. His outgoing personality made him a staple of downtown for many in our community. Jay truly loved catching up and having a good time with others.

Jay's hobbies included cooking for family and hosting barbecues for friends. Jay was a music lover from a young age and even hosted musical concerts at his parents’ home when they were out of town. He was particularly close to his mom, especially since his health started to decline in recent years. Jay enjoyed traveling and dinners together with her. He and his brother bonded over discussions about the latest movies. He was a dedicated fan of the St. Louis Cardinals, the Kansas City Chiefs and the St. Louis Blues.

Jay was known for his carefree spirit and sense of humor, always aiming to bring joy to others through laughter and a wide range of funny facial expressions.

Survivors include: his mother, Debbie Cheshire; one brother, Ryan J. Cheshire (Jennifer); maternal grandmother, Mary Frank; seven uncles, Tom Cheshire (Jan), Steve Frank (Jane), Tom Frank (Debbie), Richard Frank (Rebecca), Harry Frank (Lisa), Gerry Frank (Sue) and Tim Frank (Laura); seven aunts, Samantha Cheshire, Madalynn Bell (John), Nancy Schneider (Gary), Sue Danner (Jon), Gloria Wolfe (Marc), Terese Molinere (Tim), and Christy Miller (Shaun); and dozens of loving cousins.

He was preceded in death by his father, Steve Cheshire; his maternal grandfather, Elmer J. Frank; his paternal grandparents, Joseph and Lucille Cheshire; one uncle, Mike Cheshire; and two cousins, Mike Frank and Dalton Frank.

SCHEDULE CHANGE: The location for Jay’s visitation has been moved to Immaculate Conception Church. A prayer service will be held at 3:00 p.m. Monday, November 6, 2023, at Immaculate Conception Church with his visitation following from 4:00 p.m. until 6:00 p.m. Monday at the church.

A gathering to celebrate Jay’s life will take place starting at 7:00 p.m. Monday at Bones Banquet Hall for friends and family to continue to share memories for the rest of the night.

Mass of Christian Burial will be conducted at 12:00 p.m. Tuesday, November 7, 2023, at Immaculate Conception Church with the Reverend I.C. Medina and the Reverend Tony Onyeihe concelebrating. Private graveside services and interment will be held at Hawthorn Memorial Gardens.

A webcast of Jay's Prayer Service on Monday and Mass of Christian Burial on Tuesday will be available to view for friends that are not able to attend by going the "photos and videos" tab of this memorial page and clicking the webcasting link.

In lieu of flowers, memorial contributions are suggested to the Jay Cheshire Memorial Fund by making donations online through this link Jay Cheshire Memorial Fund - Go Fund Me or donations can be mailed to P.O. Box 95, Jefferson City, Mo. 65102.

Funeral arrangements are under the care of Freeman Mortuary, 915 Madison St, Jefferson City, MO 65101.