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* TrappedInVillainy: He attempts to leave Waystar and escape his father's influence at the end of season 3... only for Logan to refuse to buy him out simply because he wants to keep his "number one boy" under his control. [[spoiler:This leads to Kendall being DrivenToSuicide, and he's never quite the same after surviving the attempt.]]
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* AMFMCharacterization: Kendall is shown to be a very big fan of rap music, with his very first scene on the show having him rapping along to Music/BeastieBoys in his car. The eighth episode of Season 1 also has him listening to Nobody Speak by Music/DJShadow featuring Music/RunTheJewels to pump himself up for a client meeting.
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* AMFMCharacterization: Kendall is shown to be a very big fan of rap music, with his very first scene on the show having him rapping along to Music/BeastieBoys in his car. The eighth episode of Season 1 also has him listening to Nobody Speak "Nobody Speak" by Music/DJShadow featuring Music/RunTheJewels to pump himself up for a client meeting.
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* PrettyFlyForAWhiteGuy: Enjoys listening to ‘90s rap and often tries to use "cool"-sounding slang or wear expensive sneakers when meeting with clients.
* SketchySuccessor: [[spoiler:After Logan's death in season 4, he and Roman step up as co-[=CEOs=] to run Waystar Royco, though it's only meant to be until the Gojo deal goes through, at which point Matsson will be the new CEO. Though Kendall does manage to have some moments of success, like his well-received investor presentation, on the whole, he is as he always was: not as decisive, business-savvy, or competent as Logan with some truly pie-in-the-sky ideas. Come the series finale, with him, Roman, and Shiv deciding to support Kendall as sole CEO to stop the Gojo buyout, it seems like this is just the new state of things.]]
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* SketchySuccessor: [[spoiler:After Logan's death in season 4, he and Roman step up as co-[=CEOs=] to run Waystar Royco, though it's only meant to be until the Gojo deal goes through, at which point Matsson will be the new CEO. Though Kendall does manage to have some moments of success, like his well-received investor presentation, on the whole, he is as he always was: not as decisive, business-savvy, or competent as Logan with some truly pie-in-the-sky ideas. Come the series finale, with him, Roman, and Shiv deciding to support Kendall as sole CEO to stop the Gojo buyout, it seems like this is just the new state of things.
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* AlasPoorVillain: [[spoiler:At the end of the series, Kendall loses his final shot at the [=CEO=] position and is left an EmptyShell staring out at the Hudson River, [[DrivenToSuicide contemplating suicide]] once again. While this did come as a [[AssholeVictim result]] of [[HisOwnWorstEnemy his own actions]], it's impossible not to pity him after the sheer amount of torment his father put him through ended up being AllForNothing.]]
* EvenEvilHasLovedOnes: "Evil" might be a stretch, but as selfish and corrupt as Kendall can be, he does genuinely care about his siblings and is [[PapaWolf extremely protective of his kids]].
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* ForbiddenFruit: In reality Kendall ReallyGetsAround, but he’s also the one most caged and slut-shamed by Logan, while Roman (and to some extent Shiv) gets pimped out for business deals. It’s one of the reasons why Sandy is so interested in him.
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* ForbiddenFruit: In reality Kendall ReallyGetsAround, but he’s also the one most caged and slut-shamed by Logan, while Roman (and to some extent Shiv) gets pimped out for business deals. It’s one of the reasons why Sandy is so interested in him.
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* HeelRealisation: After two seasons of self-flagellation while also trying to run away from all of it, he finally admits he’s not a good person when telling Shiv and Roman about how he killed the waiter.
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* HeelRealisation: HeelRealization: After two seasons of self-flagellation while also trying to run away from all of it, he finally admits he’s not a good person when telling Shiv and Roman about how he killed the waiter.
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* ManChild: Obsessed with teen lingo and youth culture, hedonistic, prone to misreading social situations, and pathetically desperate for his father's approval.
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* ManChild: {{Manchild}}: Obsessed with teen lingo and youth culture, hedonistic, prone to misreading social situations, and pathetically desperate for his father's approval.
* NominalHero: At his best, he's trying to outwit, expose, and overthrow Logan for his own benefit.
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* PoliticallyIncorrectVillain[=/=]PoliticallyIncorrectHero: He's neither a straight-up hero or villain, and of all the Roy siblings he's the one who cries most loudly about social issues, leading to derisive nicknames like "Wokahontas". It isn't exactly an act, but he ''does'' have misogynistic tendencies in the way he treats women and shows pretty extreme classism.
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* PoliticallyCorrectVillain: Not entirely (see below), but Kendall genuinely has no problem with minorities or gay people, having adopted an Indian child that he treats no differently from his biological son, formed a TeethClenchedTeamwork dynamic with the openly gay Lawrence Yee, and spoken up when Matsson childishly used "gay" as an insult. Additionally, while he does exploit the situation for his own benefit, he does legitimately think that the sexual abuse at Waystar [[EveryoneHasStandards is abhorrent]], and is the first to suggest a proper investigation into it.
* PoliticallyIncorrectVillain[=/=]PoliticallyIncorrectHero: He's neither a straight-up hero or villain, and of all the Roy siblings he's the one who cries most loudly about social issues, leading to derisive nicknames like "Wokahontas". It isn'texactly entirely an act, but he ''does'' have misogynistic tendencies in the way he treats women (especially Shiv) and shows pretty extreme classism.
* PoliticallyIncorrectVillain[=/=]PoliticallyIncorrectHero: He's neither a straight-up hero or villain, and of all the Roy siblings he's the one who cries most loudly about social issues, leading to derisive nicknames like "Wokahontas". It isn't
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* TantrumThrowing: The moment he learns he will not be named CEO of Waystar, he locks himself in his father's bathroom and proceeds to thoroughly trash it (before calming down and putting things back together).
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* TantrumThrowing: The moment he learns he will not be named CEO of Waystar, he locks himself in his father's bathroom and proceeds to thoroughly trash it (before calming down and putting things back together).tidying up after himself).
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* MoralEventHorizon: In-universe, Shiv and Roman view him as having crossed this not when he [[spoils:kills the waiter]] at the end of Season 1 and goes above and beyond to ensure he faces no consequences for it, but when he blatantly denies having actually done that in the S4 series finale. It's not clear if they genuinely believe his claim that it was a ploy and are appalled he'd lie to them about that, or if they know he was telling the truth and are disgusted that he would deny it to try and get the [=CEO=] job.
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* MoralEventHorizon: In-universe, Shiv and Roman view him as having crossed this not when he [[spoils:kills [[spoiler:kills the waiter]] at the end of Season 1 and goes above and beyond to ensure he faces no consequences for it, but when he blatantly denies having actually done that in the S4 series finale. It's not clear if they genuinely believe his claim that it was a ploy and are appalled he'd lie to them about that, or if they know he was telling the truth and are disgusted that he would deny it to try and get the [=CEO=] job.
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* MoralEventHorizon: In-universe, Shiv and Roman view him as having crossed this not when he [[spoils:kills the waiter]] at the end of Season 1 and goes above and beyond to ensure he faces no consequences for it, but when he blatantly denies having actually done that in the S4 series finale. It's not clear if they genuinely believe his claim that it was a ploy and are appalled he'd lie to them about that, or if they know he was telling the truth and are disgusted that he would deny it to try and get the [=CEO=] job.
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Doesn't count. He was one of the main characters since the beginning
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* BreakoutCharacter: By the end of the show, he is not only considered to be the most popular character but also one of the greatest TV characters of all time period. It says a lot when people rank you up there with [[Series/BreakingBad Walter White himself]].
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* DemotedToDragon: Goes from his ArchnemesisDad's most direct and dangerous challenger to a beholden minion when knowledge of a murder grants Logan intractable leverage over him.
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* AcquiredSituationalNarcissism: Pretty much any time that Kendall gets a taste of power, he immediately lets it go to his head.
** After taking over the company as acting CEO following Logan's stroke, Kendall proceeds to strut around the office, trying to behave and conduct business like Logan, which leads to him partnering with Stewy and [[NiceJobBreakingItHero inadvertently putting the company at risk for the rest of the series]].
** After [[spoiler:exposing the cruises scandal]] at the beginning of season 3, Kendall proceeds to delude himself into thinking he's some kind of hero to the public, which leads to him throwing wild, celebratory parties, ignoring his legal team's advice, and making increasingly pathetic attempts to paint himself as a martyr for social justice.
** [[spoiler:Tragically, as soon as he thinks he's secured the role of CEO in the finale, Kendall immediately ruins it by reverting back to his season 1 self and behaving like an arrogant {{Manchild}} while emulating his dad. This leads to Shiv voting against him, thus costing him the company.]]
** After taking over the company as acting CEO following Logan's stroke, Kendall proceeds to strut around the office, trying to behave and conduct business like Logan, which leads to him partnering with Stewy and [[NiceJobBreakingItHero inadvertently putting the company at risk for the rest of the series]].
** After [[spoiler:exposing the cruises scandal]] at the beginning of season 3, Kendall proceeds to delude himself into thinking he's some kind of hero to the public, which leads to him throwing wild, celebratory parties, ignoring his legal team's advice, and making increasingly pathetic attempts to paint himself as a martyr for social justice.
** [[spoiler:Tragically, as soon as he thinks he's secured the role of CEO in the finale, Kendall immediately ruins it by reverting back to his season 1 self and behaving like an arrogant {{Manchild}} while emulating his dad. This leads to Shiv voting against him, thus costing him the company.]]
* ByronicHero: See DeconstructedCharacterArchetype below. On the surface, Kendall checks the boxes: he's depressed, arrogant, whiny, and unbelievably entitled, yet has a lot going on beneath the surface and is perfectly capable of being kind and genuine. However, the former qualities tend to outweigh the latter, making him sympathetic, yet ''incredibly'' hard to root for.
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** Cocaine (adding to the way Logan’s raised them) makes him paranoid that everyone is trying to fuck him over, something Logan is more than happy to use, but he’s also right in “Lion In The Meadow” that dad wants him back underneath him again.
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** Cocaine (adding to the way Logan’s raised them) makes him paranoid that everyone is trying to fuck him over, something Logan is more than happy to use, but he’s also right in “Lion In The Meadow” when he claims that dad Logan wants him back underneath him again.
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* TragicHero: Kendall Roy has the potential to be a good person; hell, he even has the potential to be a good CEO. Unfortunately, his immaturity, excessive pride, and total lack of self-worth ruin anything he attempts to do, leaving him in a constant cycle of being broken and alone.
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* ElementalMotifs: Several major turning points in Kendall's arc over the series tend to involve interaction with, or take place on, a body of water in some form or other. Fittingly [[spoiler: the final image of him in the story involves him forlornly staring out at a river]].
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* MoodSwinger: Kendall's manic episodes are intense but extremely brittle, with minor setbacks sending him into a tailspin of despair.
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** Kendall has a natural talent for public speaking, delivering a strong presentation to investors in season 4, and later giving an outstanding [[spoiler:off-the-cuff eulogy at Logan's funeral.]]
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* InferioritySuperiorityComplex: He practically oozes insecurity, desperation and self-loathing despite playing at being a confident, ruthless businessman. It’s partly explained by Logan’s treatment of him, telling him he’s broken and a nobody, but also the best little number one boy.
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* InferioritySuperiorityComplex: InferioritySuperiorityComplex:
** He practically oozes insecurity, desperation and self-loathing despite playing at being a confident, ruthless businessman. It’s partly explained by Logan’s treatment of him, telling him he’s broken and a nobody, but also the best little number one boy.
** He practically oozes insecurity, desperation and self-loathing despite playing at being a confident, ruthless businessman. It’s partly explained by Logan’s treatment of him, telling him he’s broken and a nobody, but also the best little number one boy.
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-->'''Roman:''' They are a pair of randos. One is a buy-in, the other is half Rava and half some filing cabinet guy, right?
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* InformedAttribute: InUniverse example. Whenever Kendall declares himself the eldest Roy sibling to justify why he should be the new Waystar CEO, everyone else immediately points out that Connor is actually older. That said, it's still MetaphoricallyTrue since Connor has no interest in inheriting his father's business.
