Gregory “Gregg” Cheshire of Overland Park Kansas passed away surrounded by love following complications with surgery on May 3rd 2026, leaving not only family, but a village who adored him more than words can express.
Gregg was born March 14th 1960 to Sue Ann and CB Cheshire in Louisville, KY. His family moved several times before settling in Olathe, Kansas. He attended the original Olathe High School (now Olathe North) and graduated in 1978.
Gregg loved cars and all things mechanical-there wasn’t anything he couldn't fix, at least according to him. He had a natural understanding of how things worked and took pride in using his hands to make things right. For a time, he worked for others before following his dream of owning his own mechanic shop. He built Cheshire Automotive from the ground up 26 years ago guided by the simple but powerful principles of honesty, integrity, and treating people right. His word meant everything and the trust he earned from customers, friends, and family was a reflection of the man he was every single day.
Gregg had the biggest heart and would help anyone without hesitation. He was full of warmth, humor, and quiet strength- what we called a “porcupine marshmallow” a tough exterior and the softest most generous heart. He made people feel safe, supported, and loved. He was our steady place, our protector, and the one that we could always count on. Gregg loved his family above all else and worked tirelessly to build a life for us.
Gregg is survived by his wife of 32 years, Evelyn, Shawn Cheshire (fiance Robin Rich), daughter Kelly Robinson (Rob), daughter Caitlin Billings (Britt), son Ryan Cheshire (Grace). Grandchildren Katrina Cheshire, Connor Flagg, Hunter Daily, Robert Robinson Jr, Alex Robinson, Garrett Cheshire, Wayland Robinson, Christopher Billings, Isabella Billings, Great- Grandson Luca Cheshire Rodriguez, Father CB Cheshire, Sister Laura Brady (Bill), Brother Glenn Cheshire (Laura). Nieces and Nephews Weston Brady (Cheyenne), Hannah Hardy (Jacob), Hailey Brady (fiance Keaton Linford), Bailey Laing (Matthew), Libby Cheshire and Carter Cheshire. He is preceded in death by his Mother Sue Ann Cheshire and his brother Todd Cheshire. He also leaves a legion of Aunts, Uncles, Cousins and very dear friends. The space he leaves behind is impossible to fill. Gregg will be missed beyond measure and loved forever.
Visitation will be 10am CST to 10:45am CST Tuesday May 12th at The Church of the Holy Cross (8311 w 93rd st Overland Park KS, 66212) with the Rosary being prayed beginning at 10:45am. The funeral mass will begin at 11am, burial will be at Resurrection Cemetery.
A celebration of life will be held at Maloney’s Sports Bar and Grill (7201 W. 79th St. on the 2nd floor) from 3pm to 7pm.
In lieu of flowers, please send donations to the Wounded Warrior Project or Great Plains SPCA.