When they were retreating, he got hit by a crossbow bolt and died on the spot.
It was only after they left the two ships that we received a critical blow. The other large-class three-masted merchant vessel fired a large number of flaming ball projectiles and crossbow bolts at them. Old Jack was steering the ship at that time. One of the fire balls fell at the front most mast and it began to catch fire. Wilson took care of it by having their naval soldiers hack the mast down under enemy fire, and toss the mast into the sea. When he called out to Old Jack, there was no response. It was only after he got to the helm that he found him nailed to the helm by a crossbow bolt, dead.