(On a more serious note, Phil's lack of executive function, and especially his impulsivity, makes me think ADD.)
He's shown an ability to stay focused on tasks he finds mind-numbingly boring (but he loves his job d00d!) so I doubt it's attention deficit disorder per se. Getting lost and confused in certain games is probably better explained by low intelligence and
cognitive rigidity than anything else. Impulsivity, on the other hand, is a hallmark characteristic of narcissism, and of the
Dark Triad more generally. It is strongly correlated with
neuroticism, which in turn has very strong links to anxiety disorders.
Concerning Phil and the Dark Triad: I see someone with strong Machiavellian (manipulating people, planning) tendencies coupled with obvious narcissism, but lower levels of Factor 1 psychopathy. True psychopaths are incredibly goal-oriented, tend to be thrill-seekers, tend to be vain and promiscuous (using sex as a tool to manipulate people) and are often very extroverted. They also don't express anxiety in the same way normal people do - their affect when frightened remains flat. Seeing as you can read Phil like a fucking book when he's been caught in a lie, he probably wouldn't register any of the typical brain abnormalities associated with primary psychopathy on an MRI. That said, the second factor (Factor 2) of psychopathy in the two-factor model is often seen as a byproduct of other disorders rather than the result of difference in brain regions like with primary psychopathy. It includes traits like impulsivity, being easily bored, lacking long-term goals, being irresponsible, going into fits of rage, etc. Factor 2 psychopathy lines up fairly well with what we see in Phil, but I would still rate the overall prevalence of psychopathic traits as low, with a tendency to be elevated at times.
With the
Five-Factor Personality Model, Phil appears to be low in agreeableness, high in neuroticism, low in openness to experience, and low in extroversion. Conscientiousness is tricky because his autistic scheduling, obsessive guide-reading and general persistence reveals a conscious attempt to increase conscientiousness, but I think this is a rather restricted, pragmatic adaptation specific to his "business", and doesn't reflect an overall trend towards low conscientiousness as a personality trait.
Overall I think his autistic scheduling, his need to finish games even if they're doing poorly (cognitive rigidity), his neuroticism and impulsive tendencies, and potential "behind the scenes" anxiety all point to him potentially having
Obsessive Compulsive Disorder (OCD). This is a condition characterized by intrusive thoughts leading to a conflict which then needs to be resolved in some manner. For example, a hand-washing OCD sufferer frequently thinks that their hands could be dirty, and this spawns a conflict (do I have dirty hands?) which must be resolved by washing their hands; the idea of being unclean completely dominates their mental landscape and causes immense stress until the thought can be dispelled.
There are different manifestations of OCD, some of which can be entirely mental: conflicts spawned in the mind, and resolved within the mind through -potentially- hours of self-debate and cognitive distortions. I think if Phil has OCD, he likely suffers from intrusive thoughts related to things his detractors say about him, his current reckless spending, his past mistakes, his self-worth, etc. I think it's very likely he sits on his couch for hours marinating in some sort of mental copium, aided by gin. His avoidance coping (the way he shuts himself off from the world) is reflective of a desire to avoid being forced to ruminate for hours. He doesn't want to have to debate with himself how he's a "changed man" and yet he does so almost every day on his prestream. These daily "changed man" speeches are part of the compulsive aspect of his OCD. He is compelled to remind himself and his audience of why he did nothing wrong, every single day.
Generalized Anxiety Disorder (GAD) is a strong runner-up. The only meaningful difference between OCD and GAD in Phil's context is whether or not the intrusive thoughts simply cause stress, or actually force him to argue with himself and seek reassurance. I would argue his repetitive speeches and constant cognitive distortions point more towards OCD, because he's actively attempting to do something about the ruminations, and that something is the same thing, every day, usually for at least an hour.
TL;DR: his schedule tism, daily rants about the same personal issues and 4:00 AM gin tweeting suggest OCD (Obsessive Compulsive Disorder) but GAD is a possible differential.
