James P O’Sullivan, 71 of Essex Junction, Vermont, passed away at the Colchester Respite House, on June 9, 2026, with his loving wife Amy by his side. Chelsea hollering, "Look whose coming, Dad I'm right here, take my hand, we're together again!" 

Jim was born on April 3rd,1955 in Burlington, Vermont, living his 71 years in the house he was born and brought up in. Jim graduated from Essex High School, Class of 1973. Jim then went on to work at Ski Dynastar and Rossignol as their warehouse manager.

Jim married Amy Gregory on April 14, 1990.

He enjoyed traveling to ski shows in Las Vegas with Amy, where they discovered the world of gambling. He and Amy visited casinos near and far, win or lose. 

On November 22, 1991 they were blessed with a precious daughter, Chelsea Marie.

Jim spent endless hours with Chelsea "Cheech" on the floor playing look who’s coming with small figurines named after all of us. Cheech‘s personality was a reflection of Jimbo‘s;  she worshiped the ground he walked on.  In 2011, we lost Chelsea Marie.  Jim was never the same, from that day forward.

After the closing of Ski Dynastar, he went to Farrell Distributing, also as their warehouse manager.  Jim finally ended his working career retiring from Farrell Distributing.

Jim lived with health issues most of his life, getting worse from time to time, he earned the name “Jimmy nine lives”, as he continued the fight.  Jim continued to spend most of his time downstairs in his family room. 

Jim watched a lot of TV to pass the time. He became our CNN reporter, keeping us all up on the world affairs. Jim’s love for food was endless. He frequented QVC Network, for foods that were “absolutely delicious”;  those were Jim‘s own words.  As always, Jim said it was a bargain, receiving a box most days. He loved most TV shows and movies; anything that challenged his knowledge. Jim had an amazing memory.  Ask him something past or present; he knew the answer. Jim, “Jimbo” as most knew him, was very witty, right up until the end. He had a lot of one liners which sometimes ended in his singing a song. He had a sense of humor like no other; he kept us all laughing. There are no words that can express how much we will miss Jimbo. He was one of a kind.  His wife, Amy will miss him dearly.  She was his rock, strength and love for 41 years. They continually said to each other, “I love you to the moon and back”.  Jim‘s last two weeks, he sang to Amy, “I love you forever and ever, Amen”.

Jim‘s father-in-law, best friend Dennis, who visited most every day will miss "the man in the basement" and together solving the world‘s problems.  His brother Pat called or visited him every Friday. 

Jim was predeceased by his parents, James and Marjorie Pierce O’Sullivan, a father-in-law, Robert W. Gregory, and a brother Tom (Esther).  Surviving are brothers Pat and Mike (JoAnn).  Jim leaves his father-in-law and mother-in-law, Dennis and Jody Plouffe.  Sisters in-laws, Ashley Hamilton, Abby Rice (Darren), and brother-in-law, Robert "Greg" Gregory (Ciara).  Jim also leaves nephews Jack Hamilton, Jonah and Hayden Rice, nieces Ella Rice, Lucy and Millie Gregory. They all meant so much to him.

Jim had a love for cats. He is leaving Stella;  his kitty companion.

We would like to thank the staff at the McClure Miller Respite House for the wonderful kindness and care they gave to Jim in his final days. Jim's family also appreciated their caring during these most difficult times.

Memorial donations in Jim’s memory can be made to McClure Miller Respite House, 3113 Roosevelt Hwy., Colchester, Vt. 05446. 

There will be no calling hours or services, per Jim‘s request.