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So, I have a theory about everything that G-man does in the half-life series, and that is that it's all actually part of his plan to employ Alyx in half-life Alyx let me explain. So, when he gives the crystal to the black mesa scientists which starts the resonance cascade, he does it as a sort of "contest." in order to see who is competent enough to protect Alyx during the events of half-life 2 which is why he spies on characters like Gordon and Corporal Shepard. Both of which he believes to be solid candidates for his protection job. After Gordon defeats the Nihilanth at the end of half-life 1, G-man realizes that Gordon has won and there for employs him. After that G-man reactivates the nuclear warhead that will destroy the black mesa facility, which in turn will alert the combine to come and invade Earth. He does this so that the chain of events can be set up so that Eli will die at the end of episode 2 which he can use as his bargaining point for Alyx. But before that can happen, he needs to have Alyx stay alive long enough to see her father die which is where Gordon comes in. G-man teleports Gordon right into the events of half-life 2 because that's around the time when the uprising starts, and Alyx starts to get in danger. like remember when G-man says "see her safely to white forest Docter freeman, I wish I could do more than keep an eye on you" that further proves that he just needs Gordon to protect Alyx. and also, how at the end of half-life 1 he calls it a "job" that's not a metaphor it IS a job. Going back to opposing force Corp. Shepard defeats the gene worm at the end of opposing force G-man realizes that he too, is very competent but G-man has already picked Gordon. And so, because Shepard is also very competent, G-man detains him to make sure that he doesn't interfere with his plot that he has set up because Shepard might like kill Breen or something before Gordon can.