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Ollie is a short and burly fellow. Where he has red-brown hair on his balding head, it's relatively short, save for his beard, which he has grown out a lot. Ollie wears military fatigues as well as combat boots.
Ollie has gone a bit crazy from all the chaos going on in Wellington Wells. He is a realist, as he does not deny the hunger crisis striking the town. He also swears a great deal and is very angry at those who he considers to be in the wrong (because he's in the right). However, Ollie does show some redeeming qualities, such as remorse over past actions of his. He does express a great deal of kindness to his one companion (see below).
Ollie fought in the British Army over the years, and eventually settled down in Wellington Wells. Ollie moved into a neighborhood that ended up housing many of the primary characters of the game, chief among them Arthur Hastings and Sally Boyle, among others. When the Germans invaded, Ollie had become the secretary of General Robert Byng and helped him to create a lie that would prevent the people of Wellington Wells from rising up and ultimately killing themselves. He helped to organize the creation of the paper mache tanks which would keep the people in check without actually doing anything.
Ollie also became an accomplice for the Authority. The one thing he did though that affected him the most was turning in Margaret Worthing, who was hidden away by her father Jack Worthing (later Uncle Jack). She ran when the Germans came for her, and they ultimately shot her to death. This ended up haunting Ollie and changing his views about everything.
Sometime after the Germans left, Ollie fell into a depression, and people, with the exception of Victoria Byng, turned their backs on him. He later asked a grown-up Sally to create a drug that would scramble his memories, in order to forget what he did. She complied, and he began to go crazy. Unexpectedly, however, he began to hallucinate a manifestation of Margaret, who helped him get back on his feet. Ollie still did not remember what he had done, though, and came to believe that he was Margaret's father and that Jack had turned her in and gotten her killed.
He began to oppose Joy, and left the city proper to live out in the wastes in the Train Station. He became more and more wild, often coming into conflict with the Headboys. However, a chance encounter with Arthur seems to give him a new purpose in life: revealing the truth to the people.
Events of We Happy Few
Arthur encounters Ollie after seeing him harassing the Headboys from atop his cathedral. Ollie initally doesn't recognize Arthur, and tries to attack him, but Arthur eventually gets through to him. Ollie is seen talking to an unseen character who he keeps calling Margaret. Arthur reveals his plan to get out of Wellington Wells and Ollie agrees to help him in exchange for Arthur helping him rob the Home Army at the Military Camp. Ollie tells Arthur how to shut off the power, although he leaves out the part about the alarm. Arthur, after going through the military camp, reveals to Ollie how the tanks are all paper mache, and that the people could have fought back against the Germans, all while realizing that he lied his way off the train. Ollie, also shocked, appears to go back on their deal a moment later, but changes his mind and gives him a random piece of machinery that will make Arthur look like a credible bridge inspector (through trickery). They say their farewells to each other, and Arthur continues with his journey.
Ollie is not seen during Act Two, but he is mentioned by Sally Boyle upon searching the train station, after the events of its destruction.
Ollie learns from Arthur that the tanks were paper mache, and Margaret begins to ask questions about his relation to the lie, as he was General Byng's secretary. Ollie insists that he had no idea about it, and after Arthur leaves, decides to go and ask Byng himself the truth. At the same time, the Headboys begin to set off explosives around the cathedral, and Ollie escapes via parachute.
Making his way into the Military Camp with the help of a friend, Ollie barges into Byng's office and asks him for the truth. Byng reveals that Ollie did not only know the truth, but he was complicit in the act, and ordered the the newspaper to help create the paper mache. Margaret is upset, and Ollie brings up the fact that people seem to be starving in Wellington Wells, and asks Byng for help. Byng, however, counters with the fact that not only would they not listen to him (given how he's forced to live on the outskirts of the city), but would probably be murdered for suggesting it. He goes on to state that the Executive Committee would be equally unhelpful, possibly more so. Ollie suggests getting help from Victoria, but Byng becomes enraged at the suggestion of using his daughter and calls for the guards to come and eliminate Ollie.
Ollie escapes with the help of his friend, and decides to make his way into the main city to get help from Victoria. Once he reaches her, though, it becomes apparent that she doesn't want people unhappy, as she remembers what they did, and tries to turn in Ollie, but he chokes her out and ties her up. He then forces her off of Joy for a while and tries to interrogate and convince her to help him, while she becomes increasingly erratic and begins to remember more of what she did. Eventually, Victoria escapes by tricking Ollie into letting her go, incapacitates him, and calls the Bobbies on him.
Ollie escapes this too, and decides to make his way to the Executive Committee's building, only to find that they have been trying to desperately forget the fact that the food production is falling apart. Concluding that they're incompetent, Ollie then decides to try and force Uncle Jack to help him, and goes up to his studio, only to discover that it's been abandoned. He then finds a recording, and upon playing it, it and Margaret reveal to Ollie that Jack was Margaret's father, and that Ollie turned her in. The rest of the broadcast reveals that Jack tried to tell everyone in Wellington Wells about the food shortage, and how they need to go off of their Joy in order to solve their problems, but Jack goes berserk and smashes the camera with a cricket bat, disappearing altogether.
Distraught and crying, Ollie breaks down and begs for forgiveness, stating that he never thought that they would kill Margaret. She tells Ollie to broadcast the recording to the people, which Ollie agrees to. Fighting off Red Bobbies and continuously making sure that the equipment doesn't break down, Ollie eventually finishes the broadcast and escapes to the roof of the building. Margaret appears to him one last time, and tells him how he needs to let go of her. Ollie finally decides to make peace with himself, and escapes Wellington Wells on a small blimp, while taunting the people from up above and peeing on them.
Ollie is seen during Constable Peters' monologue, letting go of the picture of Margaret that he has been keeping on him this whole time.
Ollie was a former neighbor of Arthur and the boy would play in his house.
Ollie's abilities are centered mainly around combat as he can take down Bobbies and Doctors along with Wellies with red hats instantly turning hostile against him. Ollie is also diabetic (or as the game calls it, "Unwell") and so the player has to control his blood sugar by crafting syringes made from honey or eating different foods like pies or scotch. If it goes too high or too low, Ollie will suffer negative side effects until the player uses a syringe or food to bring it back to normal. He has the most unique abilities compared to Arthur and Sally but they provide more negative effects than positive ones:
- Unwell: Must use syringes to regulate blood sugar. (Low and high blood sugar have negative effects.)
- Slow: Can't run fast. (-20% moving speed.)
- Strong: Can choke out unaware people, including bobbies and doctors. (Can carry more weight. +33% inventory capacity. Stealth takedowns enabled on all types of NPC.)
- Troublemaker: People don't like Ollie, for excellent reasons. (Wellies with red hats will automatically aggro upon spotting Ollie.)
- Mechanic: Mechanically adept. Chemically hopeless. (Can't use chem tables.)
Since Ollie's style of play centers more on combat, as he doesn't have a Stealth Skill Tree and instead has Combat and Survival along with Super-Duper. His Super-Duper abilities allow him to throw things farther and inflict more damage, give a small chance to render enemies unconscious, have any weapon that he uses degrade more slowly, and allow him to use less stamina while fighting and blocking. It also gives him the ability to attack faster and have the chance for enemies with less than 10% of their health to run away.
- He cannot use chem tables.
- It is mentioned by one of the Home Army NPC's that Ollie was stationed in Punjab at one point, a province in British-India.
- James Maxwell mentions that he served together with Ollie at Ramsgate.
- He likes dancing.
- He could be called a "Half-Wastrel," as he can take Joy, but it is somewhat dangerous to his health, causing heavy vomiting, a sugar crash, and almost instantaneous Joy withdrawal.
- It is possible to find a letter from Ollie to Uncle Jack in mailboxes inside Hamlyn Village, simply titled "Jack". The letter doesn't directly have his name, instead saying it is from "Jacks nemesis, O.S".