When they were eight, Tom spoke to Haytham through a hole in the padlocked door between their homes. He wanted to ask Haytham if the rumors that his father was a pirate were true, but Tom's father beckoned him away before he could.
The brief conversation made Haytham realize that his family were considered abnormal, and that he was lonely. He often loitered around the door, hoping to talk to Tom again.
On the night of 3 December 1735, before mercenaries attacked the Kenway household, Tom noticed a blinking light and wondered if Haytham was inviting him for a chat. He came down to the opened passage, where the mercenaries saw him and slit his throat to silence him. Haytham came down, wondering if the light was from Tom, and discovered his body.
Tom was buried five days after his death, and the Kenways were not permitted to attend his funeral.