- "Before I joined up with Pete, my brother and I were cooped up in a old canning factory. Food for ages. Lotta fat and happy people. Then... a young girl got... taken. We followed her trail -- wasn't hard with all that blood -- ended up cornering the people who took her in this warehouse. All ten of us went in. Only I came out."
- —Oak telling Michonne about his past.[src]
Nothing is known about Oak's life prior to or as the outbreak began, except from the fact his presumably emigrated to America from England before the outbreak began, was married and then divorced, and had a brother.
Oak and his brother lived in a old canning factory stocked with lots of food with eight other survivors. When a young girl was kidnapped from the group, Oak and his group followed her trail with the blood, and cornered the people who did it in a warehouse. The entire group of ten went in, and only Oak came out. Few weeks later he met Pete near the coastline. Pete saw how heartbroken he was so he offered him a job, leading Oak to join him.
Roughly two weeks before the events of the game, Oak was joking with the others until her noticed Michonne alone on the other end of the boat. He approached her, offering his coffee to war, her up. If Michonne took it, she jokes how it isn't coffee due to half of it being whiskey. (Determinant) Oak laughs her off, proceeding to laugh about Berto telling a pun about a "mewtiny". He compliments how the man is a fine line between "the court jester and the village idiot". He then tells Michonne about what happened to his brother before he met Pete. Shortly after, he invites Michonne to play cards with the others. If she agrees, he jokingly claims he is going to win her machete, though Michonne jokes she won't let him. (Determinant)
Oak is first seen on the deck of The Companion, as Pete summons him to say Michonne is taking his shift. Oak is instantly suspicious Pete's usage of the shortwave, worried about the legitimacy of the survivor on the other end. When the sails become loose, Oak helps to tie them down. Despite Oak's protests, Pete insists on continuing his mission of saving the trapped survivor. He is left behind on the boat when Michonne and Pete leave to investigate The Mobjack.
Oak appears outside the house a few hours after the events of the last episode with Berto, Pete, (Determinant) and Siddiq in Norma's custody. She proposes they trade, Randall for her friends. As a way of showing she is genuine, she frees Pete straight away or fires a flare to reveal Oak and the crew to Michonne. (Determinant)
The two parties debate the trade, Michonne having Sam show a bag covered Randall to show/feign he's alive. As they talk, Jonas or Gabby (Determinant) express anger and a desire for retribution for what happened at Monroe. Norma tries to calm them to no avail; they kill Berto, creating a panic in the debate. Norma apologises for their actions, trying to calm the situation. However, Walkers heard the gunshot and begin to approach the group. The exchange can take various forms:
Randall is alive, Michonne makes the trade: Michonne removes the bag off of Randall, enraging Norma upon seeing how heavily beaten he is. Regardless, Norma allows Oak and Siddiq to be freed, the pair hiding behind the gate. Randall is shoved to Norma, the women cutting him free of his bindings as more Walkers appear. Once freed, Randall charges at Michonne and tackles her. In self defence, Michonne or Sam (Determinant) kills him. Norma is deeply angered, ordering her group to attack them.
Randall is a Walker, Michonne makes the trade: Michonne leaves the bag on Randall's head, shoving him towards Norma. Norma allows Oak and Siddiq to be returned. As she removes the bag from Randall's head, she realises he is a walker. She puts him down, quickly ordering her group to attack Michonne and the others.
Randall is a Walker/alive, Michonne does not make the trade: Due to the growing tensions, Michonne calls the trade off. Angered, Norma shoots Oak in the stomach, causing Pete to instinctively shoot Gabby/Jonas dead. In the commotion, Randall tries to break free from Sam or is thrown forward (Determinant), promptly shot by her. Norma goes to attack but is kicked down by Oak. Siddiq makes it inside as Norma orders her group attack.
Randall is a Walker/alive, Michonne signals Paige: Michonne seizes the moment, signalling Paige to kill Norma. She takes a shot, successfully hitting Norma in the shoulder. Her companions are shocked at the attempted killing, shooting at the group. Oak knocks Norma down as he runs, ensuring he and Siddiq make it to the house alive. The scene now plays out as if the player verbally refused to trade.
If Oak was successfully traded and not shot, he is gifted a pistol by Pete in an effort to defend the house from their attackers. He is quickly separated from the others by a Molotov induced fire, making it out through an upstairs window. He is soon joined by everyone else, the group fleeing soon after.
If Michonne doesn't cooperate with Norma in the trade, Norma will shoot Oak in the stomach which causes him to fall to the ground, before dying from the wound he kicks Norma in the leg which causes her to fall to the ground buying Michonne and the rest time to defend back at her. Seeing as his brain was not destroyed it is likely that he turned.
This list shows the victims Oak has killed:
- His Brother (Indrectly Caused)
- 8 unnamed survivors (Indrectly Caused)
- Possible a few members of Monroe (Determinant)
- Possibly numerous counts of zombies.
- "This is a bad idea, Pete. You want to find more people, your're forgetting what people are like."
- —Oak to Pete about the dangers of helping other survivors.[src]
While Oak seemed to respect Pete as the captain of the ship, they had a difference in ideology about helping other survivors. While Pete wanted to help survivors, Oak said their goal should be self preservation. Pete and Oak seemed to have occasional fights between each other about this. Oak also blamed Pete whenever something bad happened to the crew due to Pete's trying to help people, showing that while Oak respects him as the captain, he is more than willing to call out Pete's decisions if he has a problem with them. when Oak was taken captive, Pete seemed concerned about Oak's safety. Also if Oak gets killed by Norma, Pete will plead with Oak's dead body to get up.
- "I despised the lot of them when I first got a board, but they grow on you. Like mold they are -- No no sorry. That's shit isn't it?"
- —Oak to Michonne about The Companion Crew[src]
Oak and Michonne seemed to share a decent relationship. Oak is shown to see some sort of kinship with Michonne, as both have lost people they care about, and were unable to do anything about it. Oak reveals his past to Michonne, and afterwards offers to deal her a hand in cards. Early in Michonne's life with the crew, Oak, despite his distrust of strangers, seemed to make an effort to get to know Michonne. When he sees Michonne hanging over the railing of The Companion, he comments on how he would go in after her if she jumped in because she was of them now.
- "You can call it what you like, but we shouldn't be tryin' to find people. We should be staying the hell away from them."
- —Oak to Siddiq about finding people. (Determinant)[src]
Oak and Siddiq work as crew mates, but it is unknown if they are actually friends. Oak says he warmed up to the crew after some time, so it can be assumed they have a stable relationship. Siddiq has called Oak paranoid in the first episode. they seem to have conflicting views about finding survivors.
- "It's a fine line between the court jester and the village idoit. You can guess which side I think he's on."
- —Oak to Michonne about Berto. (Determinant)[src]
Oak and Berto seemed to have a stable relationship, although they are not seen talking much throughout the course of the game. Oak seems to view Berto as a bit of a jokester. It is unclear if this means that he likes him or not.
- Oak is the first British character to appear in The Walking Dead.
- Oak is the only crew member of The Companion that has a determinant status.
- Additionally, him and Samantha, are the only characters in the mini series with a determinant status of alive or dead.
- It is unknown what happens to Oak if he lives, as he doesn't appear when Michonne and Pete return in comic since he is determinant. Meaning Oak could have died, or left Pete's crew to join Oceanside like the Fairbanks did.