I'm going to leave this here in case anyone has constructive criticism.
[MATURE]
==What Makes Him Entertaining?==
*Brian Cox delivers an excellent performance, being hammy yet accurate to how some powerful people conduct themselves in real life.
*He is a very deep and three-dimensional character whose childhood trauma mixes with the vices of modern-day America and with the complicated mentality of his children, leading to one of the most acclaimed stories in recent television.
**His actions are generally understandable given his backstory, even if they're not justified.
*His conceited, brutally-honest nature is sometimes played for laughs, as the people around him don't take great offense in it or are too greedy to step away from the job.
**This is illustrated by his catchphrase, which is telling people or things (or even the FBI) to simply "F*ck off".
*He has some "evil is cool" moments where his intelligence, scheming and sharp negotiation skills are presented positively. This is mostly when he's acting pragmatically and trying to save the company from genuine threats.
*Sometimes the punishment he delivers on his children is well-deserved and intended to teach them a legitimate lesson, such as when he scolds Roman for sexually harrassing Gerri.
**He also dies having outsmarted Kendall, Shiv and Roman at almost every turn, which kind of proves his point of them not being effective business leaders and not fit to inherit the company.
==What Makes Him Detestable?==
*While he presents himself as a Magnificent Baddie who only does bad things pragmatically for the sake of his company's (and family's) success, and while he has many "evil is cool" moments of top of some genuine redeeming traits, the show demystifies his figure by showing how petty, brutish and needlessly cruel he can also be, with this being one of the central points of his character and of the whole series. Some of these less-than-magnificent qualities or moments are:
**Being racist and sexist, on top of unfaithful to his current wife Marcia and his ex-wife Caroline while they were married.
**Using his News Division to spread propaganda and fake news which generally make the World a worse place to live in.
**Allying himself with virtual fascists like Mark Ravenhead or Jeryd Mencken, even directly helping Mencken become president of the United States.
**Acting cruel to his children at some moments where they genuinely tried to do the right thing or be useful to Logan.
**Venting Kendall's drug addiction to the public out of spite for Ken betraying him.
**Once slapping Roman so hard that he loses one of his teeth.
**Calling Roman the f-slur (though only in a joking manner)
**Ordering Kendall to close down Vaulter after they threaten to unionize, leaving all its employees jobless.
**Sending Connor's mother to a mental asylum while he was a child, scarring him deep into adulthood.
**Giving his grandson (Kendall's son) a plate of food that was potentially poisoned, only to mess with Kendall.
**Turning a blind eye to the murder and sexual assault going on inside his Cruises Division, and not expressing any care for the victims.
*His mental faculties are shown to have degraded with age, with many characters mentioning he's not as sharp as he used to be in his prime. While this is not a bad thing by itself (and can be seen as sympathetic in some way), his refusal to step down highlights his arrogance, showing he isn't so above putting his ego over the needs of Waystar.