howard hamlin, at the start of bcs in the first seasons, was undoubtedly harsh on both jimmy and kim and that is also acknowledged by chuck later on
soon, chuck actually sides with jimmy, seeing that the things that he's doing is absurd and ruins the company (hhm)
however, this behavior isn't actually howard's fault. if you look throughout the series, howard doesn't seem to acknowledge that his perfectionist and strangely professional behavior is actually hurting others. he obviously has his own sense of insecurity rooted way before anything in bcs like every other cast member, but he is thrown out of the ground and dismissed because of him being an "antagonist" in the series.
after jimmy and kim separates from hhm and chuck's death, howard actually seems to realize his wrongdoings and tries to get better. he even shows jimmy his declining physical health.
however it all stops when jimmy and kim get drunk at a hotel and start suggesting to ruin howard's career, and it was mostly jimmy who kept on carrying on with the shenanigans because kim actually stands up for jimmy's wrongdoings in the first place. overall, it's both their fault for destroying howard to his eventual death, but jimmy also kept his "charming" demeanor to incorporate that to kinda manipulate kim and others around him.
we literally see the destruction and decay of howard hamlin from the start of jimmy's uprising and the "pranks" acted upon howard. these actions literally made everybody despise howard and his last moments were when he was a drunken, broken individual who has lost hope, and can't cope with the framing allegations anymore.
he might've been an obstacle for jimmy and kim, but he was an innocent man and not many people seem to realize that.
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