Christopher Winchester has a sick sense of humor, viewing the world through dark colored glass. He has a biting sense of black humor, often laughing at things that most people would find reprehensible or down right soul crushing. As a result, those that are not used to his brand of humor often find Christopher Winchester downright unbearable or overly morbid. At the same time, his cynicism can be useful for seeing through the optimistic altruism of those he encounters.

While Christopher Winchester will see a job through to its conclusion and put forward his best effort, it’s still just a job. Christopher Winchester's true loyalties lie to his friends, and through thick and thin,he will stand by them and die for them if needed. This loyalty is reserved for those who have earned Christopher Winchester's trust, putting him at odds with other Mercenaries that are only doing a job for the money. This also makes it harder for employers to trust his motives, often times creating extra competition and difficulty finding work. None of it matters to Christopher Winchester, though, because loyalty to his friends is not something credits can buy.

While generally laid back and more than happy to offer a quip of sarcasm, Christopher Winchester's entire demeanor changes once combat begins. He becomes focused and quiet, with his smile replaced with a look of grim determination.

Christopher Winchester has a military background, and draws upon his experience to tackle the obstacles in his life. This makes him decisive, efficient, and fearless; provides him with a strong sense of duty and strength; which tends to influence his ability to fight and lead. However, a rigid mind is less compassionate towards individuals and less imaginative, and Christopher Winchester sometimes risks appearing callous, relatable, or incapable of compromising.

Growing up on Krownest, Chris picked up Mandalorian Core and used it in close-quarters combat up until he enlisted in the Iron Legion. As part of his training he was taught the Imperial Martial Arts System. Throughout his career he has melded the flexible and unconventional style of Mandalorian Core with the disciplined style of the Imperial Martial Arts System. This combined form of the two martial arts allows his movement to flow between rigid and fluid and to keep him opponents on guard. Chris is still largely limited in scope when facing an indirect foe, or ranged threats.

Chris has had some of the best training the Iron Legion has to offer when it comes to their special forces. Throughout the grueling training he was taught him to survive in most environments and maintain stealth. He is mostly at home behind the scope of a slugthrower sniper rifle. Chris stays away from the main battlefield, picking off high-value targets from afar. Because of the nature of sniping, Chris' attention is focused to his scope and not to his surroundings allowing others to easily get the drop on him.