John Weir is a master operative in corporate espionage. But as skilled as he is, there is also a lot of trauma that gets in his way. However, throughout Rabbit Hole Season 1, we see him manipulating a hedge fund manager to sell his stocks based on a fake broadcast, successfully pulling off the Banomar-Group assignment, stealing Miles’s communications data from the police department evidence room, stealing Nora Evers’ case from 1550 Girard, and finally bringing down Crowley. In all these missions, he shows high-level intellect in the way he manipulates people and creates situations to get what he wants. He is also great at cryptology, which Miles has helped him learn since they were kids. But his childhood was accompanied by trauma, as he found his father dead (he shot himself in the face) as a teenager, but in fact, he was abandoned by his father. So, he grew up devoid of the love of a father. We do not know what happened to his mother, but we know that he grew up in a boy’s hostel and that Miles was his only friend. We also know he is divorced.
At the base level, we can say that while John’s career is all about manipulating the truth, his greatest battle (yet) comes in the form of his search for the truth i.e., finding Crowley. And what’s ironic is that he had a whole team when he was making money out of truth manipulation – which is morally wrong – but when he was searching for the truth, he was all on his own. We can say that his team gave him confidence and it was visible in the way he carried himself. But after he lost his team, that confidence disappeared. It was Hailey in whom he found a safe spot. Just like his team, she helped him keep in touch with his emotions and not be a tactical freak all the time. In fact, she is also the one to whom he opens up about his anxiety. Although it takes time, John realizes that she is not a part of the world he belongs to and that itself makes her better than him, emotionally speaking. The reason we say it takes time is because John didn’t kiss Hailey the first time he wanted to but just told her that he wanted to kiss her. It is only in Rabbit Hole Episode 8 that he kisses her and realizes that she is just as genuine if not more than what he thought.
In Rabbit Hole episode 7, John tells Hailey that, in the absence of a rational explanation for the situation he is in, his mind automatically begins visualizing every other possibility. He is unable to accept Miles’s death, so he tries to reach him by using the secure chat in the game on his phone and tablet, thinking that Miles has gone into hiding and will reply soon. He even imagines his father, Ben, say that he wants the Data Act to pass. This is because he is unable to find an answer to the then-useless documents in Nora’s case. Thus he snaps at Ben because he has to feed something to his brain as an explanation or an answer. At the end of Rabbit Hole episode 7, he imagines shooting his father because, for a moment, that seems to be his way out. Miles was the only one who knew what to say to him and could calm him down during such moments. This reaction might not just be a result of what he has learned by staying with Miles but of the trauma of seeing his father dead, which resulted in him searching for an answer that would serve as a window to vent out the feelings of helplessness and even fear. Maybe he didn’t try to bring back his ex-wife because he knew he would end up abandoning her and their child if they had one, just like his father abandoned him and his mom. On the other hand, John is probably with Hailey because he sees that she has an affinity for his job and, subsequently, an ability to understand him and the stomach to deal with the dangers that accompany him. This was far from the case with John’s ex-wife, who left him after being kidnapped by John’s competitors. This is not to say that Hailey would be safe; maybe even she had a limit, as she should. But she might not also run at the first sign of trouble.
As for John’s relationship with his father, we do not know just how much of his intellect was sharpened by his father, if any. But it is clear that both share the trait of being exceptional tacticians. Despite how much John may hate Ben, he listens to what Ben has to say, and it is not just because the threat is to national security. There is more to it. We know John is angry at Ben for leaving because he didn’t expect him to. He is angry because he missed him. And maybe, deep down, listening to Ben was his way to show just how much he missed his father, i.e., it’s normal human emotion at play. When we love someone, we tend to them. As far as Ben is concerned, he doesn’t treat John like a random guy whose help he need to bring down Crowley. He treats John like his son, telling him everything that he needs to know while listening to John’s harsh words because he knows what he did was wrong. John is absolutely not wrong to be angry at Ben, and Ben knows it. But he doesn’t let John’s anger cloud his judgment. He keeps reminding John of the reality of things and brings him back on track whenever he seems to be going off track. At the end of Episode 7, when John apologizes to Ben for pulling the gun at him and is visibly shaken for what he just did, Ben tells him that there needs to be no more apologizing. This is a cathartic moment for both father and son. Finally, towards the end of Rabbit Hole Episode 8, we see John tell Ben that he played the narrative till its end, just like Ben taught him. This proves that he was trying to impress his father, maybe a little bit showing off as well and trying to prove how effective a tactician he really is, just like his father.