When he first arrived Jack moved into a boarding house while he looked for a job and a place to live. Later on, in life he was known to tell a story about the first night he got there. The way it goes is that he woke up in the middle of the night with the feeling that the bed was moving. He peeled back the sheets to find them totally covered in blood. The blood was from hundreds of bed bug bites all over his legs, and the feeling of the bed moving was from hundreds of bugs crawling all over his legs and the sheets. Beyond this, he spent the first little while in Worchester working as a handyman, similarly to what he had done in Canada, and working as a deliveryman for a bakery.

Eventually, Jack got a job at the Norton Company as a tool and dye maker. He was able to work his way up the ladder a little and he spent the last 40 years of his career working at Norton. In 1931 he met Mary Katherine "Kitty" Downer. They met through mutual friends (Either the Boylans or the Harities, both of whom are still family friends) and were married in 1932. Kitty was an Irish Immigrant from Westport in County Mayo on the west coast. She was 25 when they got married. They had their daughter Carol in 1943. In 1944 Jack and Kitty bought a triple-decker, "Close to the Catholic Church for my wife, and close to the school for my daughter". They lived on the third floor and rented out the others. For years through Carol's childhood, the family would go back to River John for a few weeks in the Summer. Jack died on December 7th, 1984.