Little is known about Jack, except for the following story in Willard's History of Greenfield (Massachusetts). At the time, he was 40 years old and friends with two African American girls, one of whom was named Phillis. For fun one day, the girls both climbed into a barrel and rolled themselves part-way down a hill. They then persuaded Jack to try it, but his experience was not as pleasant. He rolled all the way down and the barrel collided with a tree and broke apart, leaving Jack badly bruised. This did not, however, deter him from trying to court Phillis. She was not interested though, and decided to put an end to his visits in a rather dramatic manner. As she was carding tow (brushing flax for spinning) during one of his visits, she surreptitiously dropped some near his feet and then "accidentally" dropped a lit candle on the tow. Jack suffered minor burns but was not completely deterred until Phillis "treated" his barrel ride wounds with salt. The poor man took the hint and never visited her again.
Sources Consulted
Willard's History of Greenfield, David Green, 1838, pp.142-144