Gregory "Gregg" Cheshire, Age: 66
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Mar 14, 1960---May 03, 2026

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, son Shawn Cheshire (fiance Robin Rich), daughter Kelly Robinson (Rob), daughter Caitlin Billings (Britt), son Ryan Cheshire (Grace). Grandchildren Katrina Cheshire (finace Ulises), Connor Flagg, Hunter Daily, Robert Robinson Jr, Alex Robinson, Garrett Cheshire, Wayland Robinson, Christopher Billings, Isabella Billings, Great- Grandson Luca Rodriguez Cheshire, Father CB Cheshire, Sister Laura Brady (Bill), Brother Glenn Cheshire (Laura). Nieces and Nephews Weston Brady (Cheyenne), Hannah Hardy (Jacob), Haley 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. 


Condolences

Pam Spencer May 07, 2026

Friend ,Shawnee ,Kansas

Evelyn, Ryan & Grace, and all your wonderful family, Im so sorry for your loss and that Gregg has passed in this life… But knowing that he was “Promoted to Heaven” and is safe in Jesus arms is the best consolation…. As hard as this is for each of you! Gregg will be in your hearts and all of ours as well…. forever!!! He was such a great man, wonderful hubby and incredible dad as well as an amazing friend to so many of us…. He will be greatly missed!! Carry on that incredible love, put your arms around each other and look for him in the people he knew & loved…. His laugh will ring on in your heart and mine.

Kerry George May 07, 2026

Friend ,Olathe ,Kansas

Evelyn I am so sorry to hear this about Gregg. Keeping you in my thoughts and prayers. Kerry George

Alex Rowe May 07, 2026

Friend of Ryan ,Brooklyn ,New York

They say the worth of a man is measured not in his words, but in his actions. In the legacy he leaves behind. I did not have the chance to get to know Gregg the way many others did, but I had the luxury of getting to know his son, Ryan. Ryan, you are a testament to the man Gregg was. Your kindness, your integrity, your love. Your ability to be hilarious, outrageous even, while still staying true to who you are. Never once when we have spoken has it seemed you were wearing a mask, pretending to be someone you weren't. Not once did I catch a hint of malice in your words, or even the slightest tinge of disrespect. You treat everyone equally, as if they were family. And from the stories I've heard about Gregg, about the times people had with him, around him, through the good and the bad, it's clear the apple really doesn't fall far from the tree. Ryan, at your wedding, while everyone was dancing, I, not being much of a dancer, saw something. Something I'm sure many others noticed too. Gregg. Standing right up there at the front of the room, not dancing but smiling. Smiling out at the crowd with a look I can only describe as pride. There he was, at his son's wedding, surrounded by everyone who knows and loves you. Everyone who, like me, got the invite and had only one thought: I wouldn't miss this for the world. In that moment, you gave him the greatest gift you didn't even know you were giving. You gave him peace of mind. He knew without a doubt that his son is happy, healthy, and surrounded by people who love him. He saw you entering this next stage of your life, and right then he knew that no matter what, you would always be okay. That you would always be loved. That you would live a good life. In that moment, Gregg was proud. Content. Peaceful, even. He knew he had raised a son. A man. A man of worth, of value, who would always do what Gregg did: welcome people with open arms, and show them the same love and support. Out of all his accomplishments, I admit I only know so much. But Ryan, there is no greater testament to the man he was than you. While I regret that I cannot be there with you today, to you Ryan, and to the entire Cheshire family, I offer my deepest condolences and my love. The road ahead may not be easy, but know that it is not one you travel alone.

Greg Skillett May 07, 2026

Friend ,Parkville ,Missouri

I knew Gregg for 30 yrs. He was always upbeat and positive loved to have fun and would do anything for anybody He will truly be missed. Thoughts and prayers to the family.

Mark Yearick May 08, 2026

Friend ,Hillsborough ,New Jersey

Dear Evelyn and family, I’m so sorry for your loss. I deeply miss my high school bestie and neighbor. Gregg always had a quick wit and a wicked sense of humor that kept the whole gang laughing. Growing up with Gregg were some of the best days of my life. He was truly a loyal, caring, and helpful friend who meant so much not only to me, but also so many others. My thoughts are with you and your family during this difficult time. I hope the many wonderful memories you shared with Gregg — filled with laughter, fun, and love — bring you comfort in the days and years ahead.

Services

Event:
Visitation
Location:
Church of the Holy Cross
Address:
8311 93rd Street
City:
Overland Park
State:
Kansas
Zip Code:
66212
Date:
May 12, 2026
Time:
10:00 AM
Google Map:
Click Here to see Location on Map
Event:
Funeral Mass
Location:
Church of the Holy Cross
Address:
8311 93rd Street
City:
Overland Park
State:
Kansas
Zip Code:
66212
Date:
May 12, 2026
Time:
11:00 AM
Google Map:
Click Here to see Location on Map