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Riddler8

This Article Contains Spoilers - WARNING: This article contains major spoilers. If you do not wish to know vital information on plot / character elements in a story, you may not wish to read beyond this warning: We hold no responsibility for any negative effects these facts may have on your enjoyment of said media should you continue. That is all.

You know you can't have sentimental attachments in this line of work. You never know what mission will be your last, or his. You never know when or if you're gonna get betrayed. As a rule, I don't trust anyone... and I don't invest anything into anyone. That way I always have a clear view of everything. It's what makes me strong. It's why you, and he, have no hope of beating me.
~ Winston to Fiona Frost
So you're WISE, right? That's a really good disguise. Could you actually be him? Could you be Twilight? We did an op together, remember? But I never got to see your face. So… Let's take a look at that illustrious face of yours. Couldn't hurt to have one more gift for the SSS...
~ Winston to an unconscious Twilight, as he attempts to unmask him.


Winston Wheeler, also referred to as The Mole by WISE agents, is the main antagonist of the Mole Hunt Arc of the Spy x Family series. He's an SSS double agent who acted as a mole within the Westalian Intelligence as their communications agent. A position he used to later steal top-secret files regarding their operations in Ostania, including Operation Strix, which he planned to hand over to the SSS. His escape is intercepted by WISE who sends out Twilight to try to capture him and stop his plans for good.

Appearance[]

Winston is a tall man with short blond hair, blue eyes, and light skin. His hair is seen slicked back with a few loose strands hanging at his face. His build is almost similar to Twilight's, but Winston is slightly taller and more muscular than him.

While on the run from WISE operatives, he had grown a beard, which he shaved off upon returning to Ostania. In Ostania, Winston dons a black suit under a trench coat. His distinguishing feature for SSS operatives to identify him with is a gemstone tiepin on his green tie.

Personality[]

Winston evokes the impression of a cold and staunch man with iron nerves. He remains calm in extreme situations and even makes time to shoot remarks at his enemies.

Aware that spies should not have any attachments, Winston makes it his rule to never trust anyone or invest anything into anyone. Because of this, he believes it is what gives him strength and deems spies who have attachments weaker than him.

Biography[]

Background[]

Originally from Ostania's intelligence apparatus Division 4, Winston went over to join Westalis's intelligence agency, WISE, in their communications division to act as a mole. There, he would pass the West's secrets to the East and is implied to have been behind the recent spy purge. During his time as an agent in WISE, he partnered up with master spy Twilight for a mission.

Winston Stealing files

Winston steals WISE's documents.

WISE HQ eventually became aware of a mole in their ranks and sought to ferret them out. However, by the time Winston was identified as the mole, he had already gone underground and taken several of the agency's top-secret documents with him. Winston left for Ostania to be received by the SSS but WISE pursued, sending their agents to stop him.

Spy x Family[]

A dossier about Winston.

A dossier about Winston.

Holding only a briefcase, Winston persists in his escape from several WISE agents, who attempt to corner him in an alleyway. As one of the agents turn through a corner, Winston attacks from above, bashing the man's head with his briefcase. As a second agent prepares to shoot him, Winston shields himself using the first and takes the opportunity to use their pistol to gun down the second man while he is distracted, then finishes off the first afterward. As he exits the alleyway, an agent attempts to ram him with his car, but Winston leaps over the car while shooting the agent. As the car crashes behind him, Winston discards the gun while letting out a sigh of relief.

According to WISE's sources, Winston has already crossed the Ostanian border in the north and is planning to meet with the SSS at the Shellbury Hotel in Shellbury, Ostania's northwest region. Winston stops at a motel, where he cleans himself up and shaves off his beard. Shortly after, he receives a call with orders to meet at the hotel.

Winston arrives at Shellbury. Heading to the top floor of a building nearby the hotel, Winston waits to receive a signal from SSS captain Gascoigne, but never gets one. Observing the streets outside the window, Winston spots Gascoigne being followed by WISE agents. Wondering where Gascoigne is going and if the meetup location is getting changed, Winston decides to stay cautious and follow him.

Fiona discovers Winston.

Fiona discovers Winston.

Little does Winston know that Gascoigne is actually a WISE Agent in disguise, who attempts to lure out Wheeler on the streets. He and other agents stage a car accident, which will allow him to identify any agents if any of the bystanders look away faster to focus on their target. Winston, in a civilian disguise, notices the crash but pauses to move his head as he quickly turns his eyes to a nearby window reflection to observe the Agent. Because his eye movement could be seen due to his hastily picked sunglasses, Fiona Frost is able to pinpoint him out in the crowd. Winston senses that he has been found out and runs, and Fiona gives chase. With the help of another agent, Fiona corners Winston, declaring their 'game of hide-and-seek' over.

With nowhere to run, Wheeler surrenders. Fiona has the other agents secure Wheeler by tying his hands behind his back and begin searching for the intel that he took. Concerned that he has the intel memorized, Fiona and the WISE agents begin moving him. However, in that instant, he jumps up, moves his arms back in front, and uses the bind to take the agent hostage. Wheeler proceeds to tell Fiona to drop the gun and threatens to kill his hostage, but Fiona ignores his threat, saying they are all prepared to die. The WISE Agent disguised as Gascoigne suddenly arrives on the scene, and, using this to his advantage, Wheeler throws the hostage at Fiona and jumps down the railing to the level below. After freeing himself with the knife the agent dropped, Winston escapes into a nearby sewage pipe.

Winston attacks Twilight.

Winston attacks Twilight.

Inside the sewer, Wheeler finds SSS agent Yuri Briar and attacks him from behind. Wheeler knows "Yuri" is actually another WISE agent and sees through his lies as his hasty footsteps gave it away. Looking at the disguise, Winston realizes he has encountered Twilight. He then makes it his goal to reveal Twilight's face and relay it to the SSS, and the two start to fight. While facing resistance from Twilight, Winston comes out on top just as Fiona catches up with them. Before Winston can unmask an unconscious Twilight, a rage-filled Fiona unleashes a forceful stamp of her foot, surprising Winston.

Winston pulls up Twilight toward him and holds his head in a position to snap his neck. He orders Fiona to throw away the gun, to which she angrily complies, crushing the gun with her foot. Winston realizes that Twilight holds some importance to Fiona and reminds her that they cannot have any attachments in their work. He then says that he has a rule to never trust or invest anything in anyone, which is what gives him a clear view of everything and makes him strong. Winston tells Fiona that she has no hope of beating him, but Fiona jumps at him with blind rage. Winston can read her attack, but the speed of her punch is so fast that it confuses him and leaves little time for him to properly react, only managing to block it with his arm.

Fiona lands her punch on Winston, punching his forearm into his face and breaking it and her right arm. Rattled, Winston struggles to get back on his feet. Fiona declares that Winston is weak for his inability to trust anyone, deeming him an empty man meddling with the world for his own amusement. She then says that her belief and thoughts of Twilight make her strong and is why she will not be beaten. Fiona throws a punch at Winston with her left arm but dislocates it when he dodges. However, Fiona twirls from the miss and kicks a powerful blow at Winston with her leg, breaking it and Winston's other arm in the process. Winston is shocked but believes that with Fiona's injuries, he can try making a safe distance away from her. To his surprise, Fiona swings a hook at Winston with her dislocated arm, defeating him.

Fiona defeats Winston

Fiona defeats Winston.

Fiona almost kills Winston, but Twilight stops her. They have the unconscious Winston tied up, and after the WISE Agent arrives, he is carried out of the sewers and taken back to Berlint. The agents discuss how once Winston is in prison, he will make for a good bargaining chip and that they managed to protect their assets in Ostania with his capture.

Abilities[]

Winston defeating his pursuers

Winston defeating his pursuers.

  • Genius Level Intellect: Just like Twilight, he analyzes the situation he's in and finds the easiest way to achieve his goal within seconds.
  • Skilled Combatant: Wheeler is an exceptionally well-trained agent, being able to dispatch a group of armed agents by himself. He's also capable of fighting against both Twilightand Nightfall, two of WISE's best field agents and combatants (albeit Twilight was injured previously).
  • Skilled Marksman: Не can shoot several WISE agents while fighting off others in close range. He is also able to throw a knife into a gun muzzle with precise accuracy.
  • Enhanced Strenght: Winston has impressive strength, able to pull a WISE agent in front of him while restrained by grabbing him, leaping over him, then putting him in a chokehold. In another instance, he tried to attack a disguised Twilight by hitting him with a brick (which he broke from the strong impact against the wall). He later battled against Twilight and emerged victorious, leaving the master spy unconscious and injured (although he was already at a disadvantage due to his physical condition).
  • Enhanced Agility and Reflexes: Winston is fast enough to take down multiple agents without much trouble and run away from persecution by performing various parkour maneuvers.
  • Enhanced Intuition and Hearing: He is able to detect if he is being observed and can also distinguish the situation of a person by the sound of their footsteps.
  • Master of disguise: Winston is a master of disguise, with his ability to pass off as other people.

Trivia[]

  • Winston is the first and so far, the only antagonist to defeat Twilight in battle.
  • Some fans speculate that Winston represents Loid before he was assigned to Operation Strix. There are some characteristic features that support this idea;
    • Like the old Loid, Winston prefers to work alone. Thinking it gives him a clearer view of everything. He also underestimates the importance of emotions, and believes that having sentimental attachments weaken him, so he doesn't trust anyone.

External Links[]

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          Spy x family logo (2) Villains

National Unity Party
Desmond family
Donovan Desmond | Melinda Desmond

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SSS Leader | SSS Boss | Yuri Briar | First Lieutenant | Winston Wheeler | Chloe

Red Circus
Billy Squire | Red Circus Survivor | Vadim

Criminals and terrorists
Edgar | Hurry Taylar | Berlint University Student Terrorists (Keith Kepler) | Leonardo Hapoon | The Assassins (Snoops | Assassin Leader | Swordsman | Sickle-and-Chain Barnaby) | Arsonist | Rodger Hostman

Military Intelligence Special Reconnaissance Regiment
Snidel | Type F | Domitri | Luca

Others
Project Apple | Campbell Twins | Franklin Perkin | Gerald Gorey | Pance Karmer | Ritsuko Uragi | League of Evil

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