James "Jay" Francis Leary

March 5, 1956 ~ October 28, 2023 (age 67) 67 Years Old

James "Jay" Leary Obituary

James "Jay" Francis Leary, 67, of North Smithfield, RI passed away peacefully on October 28, 2023, surrounded by his loving family and friends after a courageous battle with brain cancer. Born in Winthrop, MA on March 5, 1956, he was the son of Alicia (Barclay) Leary and the late James R. Leary. He was the former spouse of Marilyn (Pestana) Leary of Cumberland, RI.

Jay was a truck driver for 45 years, always bragging about his impeccable driving record. He enjoyed his time bowling with his best friends and playing cards. Jay had a strong love for music, especially classic rock. He would play his favorite songs on repeat for everyone to hear. He enjoyed riding his Harley and going on road trips to Laconia each year for bike week with his brother and best friends. He enjoyed gambling, including playing cribbage, high low jack, roulette, scratch tickets, betting the horses and football. He was a dreamer and the multimillionaire life style was only one powerball ticket away. He also had a passion for playing billiards, golf and tennis; he was quick to take your money if you were up for the challenge.

Jay was also a phenomenal skier; he was so competent in his skiing abilities that he didn’t require snowpants. His most precious memories were spent in New Hampshire teaching his children how to ski and more recently teaching his grandchildren to ski as well. His love for his grandchildren was undeniable and he would spend every weekend with them, teaching them how to bet the horses, play cards, and spoiling them with skittles all day. He provided them with a master’s degree in trifectas.

Jay always lived his life to the fullest, he never had a bad day no matter what hand of cards he was dealt. No matter what life threw at him he responded with optimism and humor. Even through the past year of his illness he never complained or gave up hope, instead he went out of his way to bring light, laughter, and happiness to his family and friends.

He is survived by his loving children; Michaela Vacca and her husband Aaron of Bourne, MA, James Leary and his wife Pim of Cumberland, RI and two beloved grandchildren, Cameron and Nolan Vacca. He is also survived by his siblings; his identical twin brother Richard Leary and wife Kathy of Johnston, RI, Karen Curran of Walnut Creek, CA and Beverly Leary of Chicago, IL. He also leaves behind his nieces and nephews; Chrystal Doyle, Tiffany O’Sullivan, Amanda Loftus, Tommy Curran and Jonathan Leary. In addition, he leaves behind an incredible group of friends that have been in his life since childhood; friends that have since become brothers and family.

Arrangements are entrusted to the Keene-Brown Funeral Home, 445 Greenville Rd., North Smithfield. Calling hours will be held on Saturday, November 4, 2023, from 3 - 5:00 PM.
 In lieu of flowers, donations in memory of Jay can be made to the glioblastoma foundation.

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Calling Hours
November 4, 2023

3:00 PM to 5:00 PM
Keene-Brown Funeral Home
445 Greenville Rd.
North Smithfield, RI 02896


Glioblastoma Foundation
P.O.Box 62066, Durham NC 27715


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