Let’s think about this logically
ABILITIES
Big Brother is the leader of Oceania from the book 1984. Due to his position, he has control of the Ministries of Peace, Love, Truth, and Plenty, which gives him access to Oceania’s military forces, the Thought Police, and the surveillance state. However, since Big Brother himself never appears in the books, we don’t know much more about his fighting abilities or anything else that could give him an edge over Kyle, especially in a 1v1 match. Kyle on the other hand has experience in close combat, having shot three criminals that tried to kill him with his AR-15. He also has some training as a medic, which would give him a moderate level of healing abilities. He also has a dedicated following of patriots, libertarians, and ancaps who would never cave to a totalitarian regime like Big Brother’s. However, they most likely do not outnumber Big Brother’s forces and would be forced to adopt guerrilla warfare tactics to stand a chance against the Oceanian Armed Forces and the Thought Police.
BATTLES
1v1 no prep time, Kyle stomps 10/10. Big Brother just doesn’t have the skills that Kyle does for this type of combat.
1v1 1 hour prep time, Kyle still stomps at about 8/10. Big Brother has more time to do his research on Kyle to find out what makes him tick and potentially train with some weapons to stand a better chance. However, he just can’t get proficient enough with a weapon to really take on Kyle, but he may get in a lucky shot.
Big Brother + Oceania vs Kyle + Patriots, Big Brother wins 7/10. With access to Oceania’s surveillance state, military, and Thought Police, Big Brother stands a much better chance, as Kyle and his patriots are forced to adopt guerrilla tactics in order to fight against a much larger enemy. Plenty of Oceania’s population will defect to the Patriots, but most will be too terrified to fight against Big Brother.