I'm sorry if I'm renumerating on dead horses (fat khet lol) but Phil is the lolcow that I cannot find a modicum of sympathy for.
Chris Chan: Autistic, had two parents that had given up on him early in his life and resigned him to a sheltered life, then, when he tried to connect with others, albeit poorly (the boyfriend-free girl sign for one) he understandably regressed even further into the throes of untreated autism and a lack of interaction and was made very gullible (Liquid Chris, the Idea Guys, all of his orbiters) and easy to manipulate. The death of Bob had been the last straw with him being in a free-fall ever since.
Cyraxx: Son of a FAS retard mother and a second-generation rapist. Sally became his guardian after his mother died in a house fire due to her leaving the oven on. Sally is not all their either and has left him in arrested development, he's effectively a twelve-year-old on permanent summer vacation, who has slipped through all of the cracks of society and left to be eaten away by bedbugs.
Wings: Big-mouthed blob with a chip on his shoulder, made it big around the same time as Phil playing CoD, and ostracized those around him because of his new-found fame, that he couldn't handle. Probably would have been well-off if he had quit early on with the 400k he made in his first few years of YT, but it got the better of him and now he's miserably shaking the tin cup for $100 a day. Unlike Phil, he is rather honest about his life, and just goes with the punches E-begging, an honest E-begger if I may. We also know that the money just goes to food and his living expenses so it's far less deceptive than the Pig's coffers.
And then it comes to Phil. He has always been this way, the Wolverine Toy, the sinecure at the Helicopter Company, the NPD, etcetera. But Phil has always been lazy and stupid, he throws the money of his dents into a furnace, he's always had addictions, poor financial management skills, and the sublime assertion that he is the smartest, most capable person in the world. I genuinely believe that the facade never breaks in front of anybody, his romantic partners, or "close friends", but is a thought in the back, VERY BACK of his head at gin o'clock as he's pulling zombie wrestlers. If he were only ethically evil, then it would have been far easier for Phil to have resolved the very profound issues he's had with addiction and interaction with others. But he is evil AND stupid, with the stupidity overshadowing the evil in his mind. He sees the people that donate to him as a source of income, nothing more, not people that he openly exploits and swindles for every five-year-old grift made up on the spot in that head of his, or even people at all, he just knows that the text that pops up in his chat are wallets unplumbed, and not people that have their own wants, needs, etc. That is why I think every relationship of his is so cold, it is all symbolic to Phil, his wife is an object to demonstrate that he is a man, once he has the wife he leaves her in her room with an allowance. His "schedule" is a routine to demonstrate that he has a job. Once he has that schedule he just shuts his brain off, snorts, acks, and ragequits childrens' games. This is how he rationalizes getting fleeced five grand out of those fighting tournaments way back when, the, what, half a million on WWEC, the BMWs that don't work anymore, and, the biggest one, his "job", being the fat twelve-year-old that would beat the other kids in Street Fighter in the Arcade, except that he does it poorly, over the internet.