Jeffrey Michael Gillespie

GRAY – Sunday March 24, 2024, we lost the best man in the whole world, my Dad. Very unexpected, very peaceful in sleep. I like to think my uncle Greg came and got him and took him to the Happy Hunting Grounds where they are now fishing, drinking whiskey and smoking cigars while laughing all the while.

He was an avid Red Sox fan, as many of you know, even tho they were terrible he’d just have faith for next year. (I personally believe this year they will win the world series) he loved baseball, and played until he graduated high school and then was on a men’s league.

He loved the Bruins, as he played hockey from the time he could lace hockey skates until he was 35 and had wrecked both his knees, which he didn’t let bother him until the last few years.

He also was a fiercely loyal Patriots fan, which I gave him crap about all the time, especially post Tom Brady, but he just laughed at me and would say just wait til this next season.

He was a really amazing golfer and played golf and built me golf clubs when I was 6 (which I still have) because he insisted I was going to be a professional golfer or my sister Becky was.

He loved everything to do with farming, tractors, trucks, and I think he knew everything about both subjects. He spent many years on the family Gillespie farm and loved every minute. He also loved working on the ranch, everything to do with cattle, haying, and also the farming wheat and barley.

He also loved everything to do with logging and chainsaws, he had gone from 100 percent Stihl saws to all Husqvarnas in the last 15 years, and sent me pictures all the time of trees he cut with whichever saw in the background. They were his babies.

Muscle cars, especially mustangs and GTOs, he was pretty passionate about, too. He loved working on his personal truck in the last few years and was pretty proud of it.

His work ethic was unmatched, he was loyal to a fault and never said a unkind word about anyone regardless of the circumstances.

His sense of humor was unparalleled, he loved “The Three Stooges”, “The Mask”, “Uncle Buck” and all the Chevy Chase movies, not to mention all John Wayne and Clint Eastwood movies.

He loved hunting and fishing, and when we moved to Montana when I was 11 and Becky was 8, and he got to fly fish and hunt in the Big Sky for over 20 years.

The last 10 years he mostly spent in Maine where he grew up, with my grandparents Lawrence and Theresa Gillespie, and his brother, Greg Gillespie, until he passed in 2016.

He plowed snow, worked on the golf course he lived on, and absolutely loved his life until he fell asleep before going to plow and didn’t wake up.

You were the best father, brother, uncle, son and friend anyone could ask for. There was no one you met that wasn’t a friend and didn’t respect and love you. You will be missed so very much and left a huge hole in our hearts, and in the community.

His life could fill several books and I only covered a few highlights, but one thing for certain, there was not a better man alive with a bigger heart and a soul that actually deserved the peaceful old cowboy death that God gave him.

We love you always, and I am proud beyond words that you are my father. I’ll miss you every second of every day.

We are having a small immediate family mass at St. Gregory’s in Gray, and then will have a Celebration of Life BBQ mid-May, date to be determined, that all friends will be welcome to attend.


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