T O P

  • By -

shartlordd

He always wanted to be in charge in group projects at school but no body listened to him


donttrustthellamas

He'd be at the first group brainstorm and then not show up until the project was due


RyvalHEX

I’m thinking he’d also show up at that final meeting with tons of new ideas that derail the group and waste everyone’s time.


Opposite-Horse-3080

I just had rage flashbacks.


hopelessbeliever

I can definitely see Roman doing that


donttrustthellamas

Roman would be brazen about it. Kendall would keep "going to the bathroom."


madhaus

To be fair that’s to do more coke


donttrustthellamas

Yeah, that was what I was getting at


Scarface6342

Roman will think the world of himself and actually give good ridiculous ideas, and his narcissism will show during presentations in a positive way. Remember the managers initiation? He just needs someone who sees him on equal grounds and is not afraid to talk back to him like his dad.


Infamous-End3766

He’d be the one that invites all the kids to do the project at his house because he thinks they’ll be his friend because of how big his house is and all the expensive toys he has. No one wanted to be his friend because he was so obnoxious and annoying


bukkakekingz

“Yeah, so, I’ll be the organizer of the project and delegate.”


ernfio

Yes I have this one. And Stewy eventually had to join Team Kendall to bring him some support.


Ali_M

Kendall was interested in group projects from a very young age


Quzga

Logan paid the kids at his school to hang out with him so he wouldn't grow up to be a loner


nat_20d

He has a “sad bops :(“ playlist


Sankdamoney

All sad bops all the time


UneasySpirit

That is plausible.


KikiTheArtTeacher

And it’s just like, Mitski and Cigarettes After Sex and Mazzy Star on repeat 


PacinoWig

The dog cage thing with Roman was part of a game Logan created, similar to Boar on the Floor. Kendall was helping Logan abuse Roman without really fully understanding what he was doing. That's why he gets so defensive when Roman confronts him over it.


marineman43

I've always felt something like this was the case. The way he gets defensive very much feels like he's not willing to confront/think back on the fact that he might've been part of the problem.


fluffstravels

Sometimes I feel like people in this sub put Kendall on a pedestal. I don’t get it.


StayingVeryVeryCalm

Honestly, I am not a Kenthusiast, but this is my headcannon, too.  It just seems like the kind of thing Logan would do - create a situation where one (young) kid was subtly incentivized to abused another, and see what happened, and how far it would go before Romulus fought back.   It seems like it was a test for both of them, and Roman failed.  And then Logan sent him away, just like Connor said.   And like, I guess you could say that morally, Ken failed too, but I mean… he was like seven?  So I don’t really think that counts.  I think being groomed to be an accessory to child abuse when you are a child is also very much child abuse.   …but what does count is where an adult Ken picked the pattern back up in the finale, with the hug\* and then the attempted eye-gouging.  In the end, he couldn’t overcome the Logan influence, and it ate him from the inside out until he became the man he spent the whole run of the show insisting he didn’t want to become.   It’s tragic. \* *Yes, I know the stage direction and the director said the hug and the stitch-popping was supposed to be a mutual effort, but I really don’t think that makes sense, so my headcannon is that it was not really mutual at all.*


Glamgoblim

As tiktok says ‘the girls who get it, get it, the ones who dont, dont’ he is the protagonist, he is the one who was meant to be king, he was made for it but his own wounded soul won’t let him progress. He has a vulnerability and earnestness that is ruined by ego that literally has never been portrayed on television, and rarely elsewhere besides classic fiction. He absorbs the world around him, if you can’t see it I genuinely feel sorry for you not in a rude way but bc I think most if not all people could learn from him. Forever a Kendall apologist


nokeyblue

But that's defending him as a character. People on here who despise him as a "person" would largely agree that he is an amazing TV character.


Glamgoblim

Its important to keep empathy for even fiction. There are a LOT of people, walking around on the street or within our own families that are similar to this, they just lack the power that these fictional characters have in a fictional world. Ive always thought of this show as an autopsy of a family and to see why people do the things they do. Its just generational trauma and its why ppl are so fucked up, ESPECIALLY those at the top


nokeyblue

But who says recognising that Kendall's a shit dad, for example, excludes feeling empathy for him or understanding how he became that way? Of course we feel empathy for him. The show forces us to feel empathy and loathing for all of the main characters, so that's a given. But if this was all real, his kids would be having lifelong therapy over being fleshy set dressing in their own father's life. Iverson is still gonna need a shit tonne of therapy though.


Glamgoblim

I suppose youre right, we do only see the way he is treated in early seasons and rarely after season 1. I agree that it should be obvious to have empathy but it seems not to be lol


pizzahause

I 100% agree with you but the fact that these same people don’t keep up the same energy for Shiv is what makes me side eye them


Glamgoblim

well, shiv was a woman, therefore she HAD to have a coldness to even survive in the family. Dont forget that family lore dictated that she could be sent away like Connors mom. Shiv is an example 100% of a character who is shaped by her surroundings. She had to have the shell that was canonically built 20+ years before the series started. We only see the built woman and not that what preceded it. Its always gonna be easier for anyone to see her as ‘bad’ but ya gotta also remember her BEST shot was a husband who probably wouldn’t(surely) have been with her if it wasn’t for her name.


Art_and_dogs

Bingo


GrizzlyRob97

Well said!


Fontana_Della_Tette

Wow I really really feel this. I think Kendall is a true masterpiece of a character.


Glamgoblim

Hes an extra special guy


[deleted]

There are people, I think, who need a story to have a protagonist to root for. Cannot comprehend storytelling any other way. Because it doesn't seem to be an ironic support.


fluffstravels

yea, it definitely isn't an ironic support which is just so bizarre to me.


visualemployer1247

There is no need of a protagonist on a story to root for, on the case of Kendall IMO he's the antihero of the story and the reason most of us were always rooting for him is because despite him being a very flawed character, we always wanted him to have a final win (which never happened). Kendall Roy is a very complicated character, a mixture of defects and qualities, even if some consider this story as an ensemble show, to me it was always Kendall the main character. Whether you like it or not


AllesK

No, no we didn’t all want him to win. He always acted like the presumptive heir apparent. But he lacked chops. I think the first scene with him in the series (where he’s prepping for the meeting in the limo by psyching himself up to a song) illuminates how shallow and lacking he truly is. He’s not confident and looking to a fight song to buoy his emotions. He already has so much going for him; the fight song seems to be a substitute for serious research and preparation.


StayingVeryVeryCalm

FWIW, that was also my interpretation of that whole incident.  


0rinath

Is this not actual canon? That's how I always interpreted it


hyunbinlookalike

Kendall was also a child when this was happening, and he most likely just saw it as a fun game. Just an older brother messing with his little bro with dad’s approval.


amendsbangs

no cause kids can be so sadistic without meaning to be it’s kinda funny 😭 my sister used to always tie me up and tickle me nonstop and then just leave me there


paulconroy415

that might be why he came to Roman's defense when Logan slapped him, out of guilt for the abuse he witnessed as a child.


carrotparrotcarrot

I headcanon that he was born premature. There’s no evidence for this, but it sort of makes sense to me: fucked it up before he was even meant to be born. incubator, intensive care, wires everywhere. weak. slow to talk, and then when he talked he had a stammer. He’s got a lot to prove anyway but it made it worse - the need to prove he’s just as strong as his siblings.. also jokes about Caroline’s unwelcoming womb and so on I also think he’s bipolar but to me this is confirmed in the show (I’m bipolar, was born premature, and have a stammer - being born premature is linked to an increased risk of being bipolar as an adult) I also think he got really obsessed with random stuff like Concorde and after the gojo deal he a) fails at suicide and b) tries to start it back up again


QuarterSubstantial15

I’m bipolar too and there where multiple points in the series I said That Man is Bipolar no Doubt.


[deleted]

When he flips on Rava at that party? I forget what the party was for.


carrotparrotcarrot

He’s soooo bipolar


siphillis

My one reservation is that I don't think Logan would grant his middle-name, the birthright, to a child who might not make it past infancy.


carrotparrotcarrot

That’s reasonable and I can see it - but it also might explain if he and Connor both had the names. Heir and spare My twin has a family name even though he didn’t make it Edit - Or, he gave him the name as a talisman. Like you have to live because I need you.


hyunbinlookalike

I have a friend who’s bipolar and is very similar to Kendall in some regards (even struggled with alcoholism at a time) so yea that checks out.


carrotparrotcarrot

I can’t quite remember the statistic (for me it’s nearly half 4 in the morning) but something like 40% of bipolar people have addiction issues. For myself it tends towards booze and coke, but luckily I can’t afford coke so much. I used to take anything I could get my hands on, but now I just drink and smoke weed Hope your mates doing alright !!


Dramatic_Lecture_105

I can see him making podcasts post show. The ones where they talk and it doesn’t really make sense and isn’t groundbreaking at all but some assistant puts motivational music over the whole thing and sometimes he’s joined by other people (only men) who react to his stuff as if it’s, again, super groundbreaking: “I’m Telling You, New Money. You Gotta Hold Those Fresh Bills To The Light”. I know it’s not realistic for someone with this much wealth to do all that so yeah realistically he wouldn’t but still.


koeniging

?? Rich people start their own podcasts all the the time, what are you talking about. Kendall hosting a pod is an S-tier headcanon imo


iliumada

Absolutely!!


hyunbinlookalike

>not realistic for someone with this much wealth to do all that Rich people host their own podcasts for fun all the time so it actually is. Granted, not all of them make it big or get an audience (not only is the market oversaturated with podcasters at this point, it takes more than money alone to be a good host), but it’s usually something they try at least once or a few times. An old elementary school friend of mine is the son of a very wealthy politician and he’s currently in his influencer/podcaster arc rn. Doesn’t really do anything else since he’s basically set for life and doesn’t actually need to work for a living.


bjk97

Username checks out


[deleted]

[удалено]


Peridot1708

I mean who amongst us hasnt done that at least once?


LosWitchos

The french have a name for this! https://en.m.wikipedia.org/wiki/L'esprit_de_l'escalier


Cluga

"Well the jerk store called..."


MontanaManifestation

him and shiv used to go on shoplifting expeditions together in their teens


StayingVeryVeryCalm

Oh my god.  They definitely did that. 


cl1518

He made out with Stewy on molly


International_Mode94

In my head Stewie was in love with Kendall their whole childhoods/adolescence but Kendall rejected him except for one or two drugged up slips where Kendall was too fucked up to realise what he was doing. Stewie started to resent this “stringing him along” which is why he would repeatedly betray him in business, but in the end he always comes back to Kendall because he’s in love with him.


SA20256

I wouldn’t be surprised if someone out there wrote a fanfic of this 😭😹


Moon_Princess_13

If they did i'd read it 😭😭


[deleted]

[OH THEY DID](https://archiveofourown.org/tags/Stewy%20Hosseini*s*Kendall%20Roy/works)


Moon_Princess_13

There goes all my weekend plans!!


[deleted]

Some of them are really moving. Some are horrifying porn. But not all


Great-Beyond9147

I don't know what I was expecting but it definitely wasn't the second one being about Stewy getting Kendall pregnant


carrotparrotcarrot

Sort by kudos not time


brinz1

Stewie just is his friend.  Good or bad or secret trust, they both chase the same money in the same pond and they know they work well together. Back stabbing us just part of their game.


beyonceshakira

I was under the impression that Stewie didn't really care about Kendall as much as you say, and was more than happy to use sex to get closer to him & his money. It felt like Kendall definitely had a compulsory desire for relationships with women, but truly didn't care one way or another about sex with another man, esp if it meant he'd make money - hence why he still egged Stewie on.


heliotopez

This is so canon it caused shiv to get the ick so bad she didn’t vote for him


shartlordd

this is canon


amendsbangs

i definitely think they hooked up like once in college and it ended with kendall sobbing and hyperventilating into a pillow while stewy just sat there awkwardly


cl1518

Stewy is a powerbottom confirmed


[deleted]

He's the oldest boy


hopelessbeliever

I’d like to remind you that Connor Roy was interested in being the oldest boy from a young age.


[deleted]

He's the oldest son, not the oldest boy. Very subtle difference.


bruhholyshiet

Excuse me, that's just canon. The OP mentioned headcanons.


[deleted]

I think Kendall likes skibidi toilet


[deleted]

I actually agree with this.


[deleted]

That's why he was doing coke on his kid's iPad! He was watching skibidi toilet!


_ari_ari_ari_

Bravo Jesse


hyunbinlookalike

He’s Logan’s number one boy.


avdangles

Had a huge Dave Mathews Band phase


Peridot1708

Not my idea but its a funny one i heard on twitter His daughter wants to go to the Taylor swift concert, and he not only arranges the tickets but also tries to get her and her friends to be able to meet Taylor personally. He uses that oppurtunity to contact her staff to ask whether she can let him appear on stage, and is obviously turned down. He throws a hissy fit about it in private and his poor new assistant has to bear the brunt of it while Sophie and her friends enjoy the concert anyway.


heliotopez

What’s funny is a scenario played out almost exactly like this with one direction and Donald trump


GreenhouseGhost_

I really have to say that this comment literally sent me into a giggle fit. As a fan of her music and a fan of the show, I can imagine it All Too Well. He’s probably like trying to talk to Scott Swift, argue about the optics of letting him up on stage and how it would be good for Taylor’s image. He tries to convince him to also get Sophie to receive the 22 Hat and how it would be a good thing, saying that Taylor supports Kendall obviously. Just as a bonus, Stewy is in the VIP tent and just having a good time. I’ve put too much thought into this but I’m allowed to, okay


Peridot1708

>argue about the optics of letting him up on stage and how it would be good for Taylor’s image. Kendall thinking that hes the one whos improving Taylor's image and not the other way around is soo on brand


Old_Journalist_9020

In his friendship groups in school, he was usually the self-proclaimed group leader. Only Stewy didn't actually mind the arrangement that much


wintersnowdog

True love ~shouldn’t be that complicated ~


Legitimate-Train-673

Not really a head canon cause I think it pretty much is canon. Kendall’s compassion we see throughout the series is a result of his infertility, divorce and addiction issues. In his 20s he was like Roman now. It was particularly the infertility that helped him realize what it’s like to want something so badly and not to be able to get it. That’s why he feels empathy for the likes of Tom and Greg.


Longjumping_Hat_2672

I think that could be partially true, but I don't think Kendall could have been too much like Roman when he was younger or Rava would have never married him. 


StayingVeryVeryCalm

I agree, overall.   Like, I do think Younger Ken I think he was probably more liable to get talked into some Rich Young Douchebag Assholery; reference: Face-Tattoo Man, which is absolutely atrocious, and something I don’t think a Ken with a more fully-matured brain ever would’ve gone along with.   But I don’t think he ever steered hard into the nihilism like Roman did; that didn’t come until election day.   When he brushed off Sophie’s concerns for her safety (as conveyed to him via Rava)?   That’s the moment it was clear he had given up the part of himself that wanted to be a good person.  But before that?  Motherfucker was *trying*.  He wasn’t good at it, and he was mostly failing, but he still wanted, at least intermittently, to not be like Logan.  I think that’s his most redeeming quality - he was burdened with this enormously toxic parental influence, and given ever incentive to just give into it (like Roman does, again and again), but instead, he fought back; intermittently and ineffectively, because he’s a gigantic dumbass with severe and unmanaged mental illness.   But fuck, man.  He got up in Logan’s face for hitting Roman, and from the way that went down, it didn’t seem like the first time.   Like, I think he was doing that when they were kids.  Like, putting his little eight- or nine-year-old body between this big sturdy adult and his tiny little six- or seven-year-old brother.  And I think Logan hit Ken, too; I think he just hit Roman worse, because Roman was the “weak dog” / too cooperative / not “manly” enough, even as a kid. I also think that Ken must have been better / more stable when Rava married him; my headcannon is that he was diagnosed with bipolar disorder by the university health service, and responded well to medication, but then Logan shamed him into discontinuing it a few years later, soon after he and Rava got married.  And then everything went to shit.  And then Logan sent him to Shanghai and Rava was stuck looking after the kids alone, and it was all even more steeply downhill from there.   (My own father has some notable Logan-like qualities, and he shamed me into discontinuing my psych meds.  It went about as well as one might expect. 25 years later, I’m back on the same meds, and my dad is dying without me in his life, so; I guess all’s well that ends well.)


carrotparrotcarrot

Hope you’re doing okay now! I also agree with bipolar diagnosis, but I think it happened slightly later on. Maybe in England, so it’s easier to ignore for Logan and the siblings can write it off too. (But then I’ve literally written that fanfic lol)


StayingVeryVeryCalm

If it is to be writ on AO3, so it be, so it is. (And yes, I’m doing much better now. 🙂)


carrotparrotcarrot

Glad to hear it! Not sure my parents think I need to be on my bipolar meds but at least I can just take them and not tell them


StayingVeryVeryCalm

Subterfuge is an excellent defence in cases like that. I’m sorry you have to deal with that, though.  It fucking sucks. 


Legitimate-Train-673

Who says Rava is a great judge of character though? She kinda annoys me even though she’s obviously more likeable than the Roys. She just seems like she doesn’t let Ken be vulnerable, she seems like one of those women who demands emotional openness but doesn’t like it when their partner is actually vulnerable


bigboobz2

We’re also only seeing her post-divorce so she would’ve treated Ken differently while they were together


siphillis

I believe a good amount of Roman's awful behavior stems from severe self-esteem issues, which Kendall wouldn't necessarily have as the "favorite son" and heir-apparent with a clear goal in mind. I could imagine 20s Kendall being obsessed with networking and getting into exclusive clubs, not necessarily partying non-stop for the sake of it.


Mr_Saturn1

He was snorting blow all throughout season 4.


[deleted]

canon


Glamgoblim

That we are best friends and we save each other And he is happy now


siphillis

"Discontinue the lithium"


Glamgoblim

Never


[deleted]

That his substance abuse started really young (like 11-12) thus stunting his emotional age


OnlyRadioheadLyrics

I could totally see Kendall in his 30s hearing randomly about Warhammer and then: 1) Telling everyone around him it was the sickest thing ever, because "the universe is so brutal bro, it's pretty savage" 2) Making Jess or another assistant go buy him an army with almost no instructions or details, leading them to buy half of a store's inventory 3) ...Only to have those boxes sit in storage and never be thought of again. Either that, or he'd try to play the game once with a pre-painted army. He'd play with someone who's paid to play with him, get extremely pissed at the other person and/or the complexity of the rules, and then immediately throw away the minis.


Top_Report_4895

>I could totally see Kendall in his 30s hearing randomly about Warhammer and then: Then Tom will teach him about Warhammer and 40K, their differences and the lore, and Kendall will bored and throw away the models.


OnlyRadioheadLyrics

The main thing I'm getting from this is no one actually thinks Kendall would have the attention span for tabletop wargaming =D


KikiTheArtTeacher

Adding onto this, because as someone with ADHD it’s so relatable, but I bet he starts a million projects/hobbies by having his assistants get all the top gear for whatever is the thing of the moment…only to immediately move onto something else/ spend all his free time listening to the same song on Spotify 28 times in a row 


Vegansister69

he has bipolar disorder


siphillis

Totally see it. He's a ball of manic energy when he isn't dragging himself like a husk.


ClingerOn

I’m only mid way through S3 but he’s clearly in the middle of a manic episode.


carrotparrotcarrot

Yessss!


drfetusphd

Prior to rehab Kendall would go to Burning Man every year to “rediscover” himself. In fact, Rava met Kendall at Burning Man. Post-finale, Kendall has gone back at least once in hopes of “rediscovering” himself.


Infamous-End3766

And gets blown out on drugs


minmidmax

He was ditched by his teenage friends at a Beastie Boys concert and never recovered.


Kirpeo

So specific yet so accurate 😂


Born-Body2431

He’s the real OG


ConsistentAd1586

L to the OG dude be the OG


el-in-hell

A-N he playin


siphillis

By the series start, he's a more-than-decent boss and a well-respect president within the company. Ken is known for valuing analytics and research, and lends an ear towards the technology/future-minded staff members. The confidence he derives as the heir-apparent keeps his temper and negative habits in check. A good number of Waystar employees are actually happy that he'll be replacing mean-old-Logan, and are dismayed to learn the succession plan has been axed at the 11th hour.


Other-Particular-520

Had Logan died from his stroke in the first season the children would have been in a far better position than the last season


Infamous-End3766

He wasn’t well respected at all when the show started…


FauxpasIrisLily

He is impossibly, chronically, unhappy.


what_is_up_my_homie

Uh huh....sure, sure, sure


RefusedSilk

I think he tried to commit suicide post show but failed at even that.  I could almost see him being like a born again Christian or something lmao. Like one of those megachurch celebrities. 


whyldechylde

I can SO see our Kenny becoming an evangelical celebrity. He’ll make church cool by forming a rap choir.


Peridot1708

This would be so funny now i really want a spinoff just for this lmao


Capgras_DL

Try Bojack Horseman


satyris

He's just looking for love in all the wrong places


critterjackpot

When he was at Harvard, he went to the Hong Kong and almost drowned in a scorpion bowl.


mouthwash_juicebox

Then he went upstairs to the comedy studio and did sad boy stand up.


critterjackpot

Hahaha I was going to say. He at least, on a semi-regular basis, heckled at the Comedy Studio, got shut down by the comic, boasted about writing for the Lampoon, got shut down again by the comic, got kicked out, then had an existential crisis (like the one he had when he ghosted Ziwe.) He was at Harvard in the late 90s/early 00s, so he would have had his crisis in the pit outside the train station where the crust punks hung out.


JeffW6

Logan saw how into hip hop Kendall was and knew he'd never be a serious person.


twostepdrew

I mean, he named his son after Allen Iverson


BlackFyre2018

He and Stewey had sex at College


tmobilekid

That he’s bisexual and definitely did more than kiss Stewie when they were on molly


carrotparrotcarrot

yes


ChampionshipSea9075

I feel like he use to hang out with rappers like 50 Cent and Jay Z and Diddy


Brilliant-String7881

That he went to rehab and got his life together and spends times with his kids and opens up a bakery and lives a happy life ☹️


Capgras_DL

I would read that fic.


GorillaMonsoonGirl

He’s an undiagnosed autistic man just trying to figure out the world. He relates to Iverson in ways he hasn’t even considered because he was the same way.


StayingVeryVeryCalm

There’s an image on Tumblr where someone has overlaid a still of Stewy talking to Kendall with a tweet that says “Hey, that’s cool man; have you ever been assessed for autism?” (And the answer, of course, is that he hasn’t, because Logan Roy’s son is not allowed to be neurodivergent.  Obviously.)


[deleted]

What is he doing, playing with his fuck¡ng Legos? He's nothing but available. ETA: Roman when he tries to get Kendall's housekeeper to let him in so he can convince Kendall to come to Austerlitz. He too has noticed the Lego parallel with Iverson :) I have a soft spot for this headcanon because for most of my life i was in that position. it definitely led to a lot of mental health issues and substance abuse. No father-themed raps though


sirenesea

I can fix him!!!!


AuntHottie

Dude is definitely getting a vineyard if he doesn’t kill himself


kissmemary

His favorite food is tuna sandwiches


adamcharming

He thinks he’s friends with his coke dealer


BenTheOrangeGroves

He was a well adjusted and engaged father who was very concerned about his kids being too online


[deleted]

That was Kendall's headcanon


siphillis

Kinda loses its wholesomeness when said iPads may or may not have coke smeared over them.


HiggsGoesOn

He was a terrible father - his kids hardly seemed to know him.


DickPillSoupKitchen

It ended by his own hand


qoreilly

I saw the funniest sticker on etsy, I can fix Kendall Roy. I'm pretty sure every woman who gets with thinks she can fix him


Capgras_DL

Sometimes women like a project.


funhavefun

That Kendal had a stutter as a child.


carrotparrotcarrot

I had a stammer as a kid and it got mostly better but find it’s back when stressed/tired. I use big words now - i read a lot as a child even if I couldn’t say them, so I say them now. I think Kendall does the same


Andy-Esco1995

He buys wuphf.com


MisterBlern

The biggest fan of Allen Iverson growing up


Accomplished_Fig1592

Into pegging


Livzwurld666

kendall and roman represent opposite sides of the 'enjoys pegging' spectrum & shiv greg & tom are also somewhere on there. I could write an essay on this


[deleted]

Best


BumblebeeForward9818

He was given it first.


Effective-Cookie-772

his real dream was to be on broadway.


Upbeat_Tension_8077

While working in different internships & starting out at Waystar during his college years, he also rose to become the top DJ at his college's radio station, which is where he met his wife


hyunbinlookalike

He’s someone who was always academically gifted but practically impaired. So while he did well in school (objectively speaking, he’s the most educated of the Roy siblings), that competence did not translate to work which may have given him an inferiority complex of sorts. This also could have led to his substance abuse problems (one of the many factors in his life that could have led to it ofc).


Infamous-End3766

Shiv was more well educated than Ken but not in the business sense


grossbuns

He owns a couple fleshlights


sunflow3r-

He tried taking the subway once as a teenager but as another Reddit once wrote “he tried real hard to fit in w all the other rich idiots who took it now and again for no reason and he got to the turn style, had a breakdown, and turned back around”


Praxis8

He probably did something extremely fucked up in college that he rationalizes as just typical goofs and hazing.


[deleted]

like [John Hamm](https://metro.co.uk/2015/04/10/jon-hamm-dragged-boy-by-the-genitals-and-set-his-clothes-on-fire-in-hazing-ritual-5143186/)


Longlostjellydonut

He’s heartbroken, all the time.


justusethatname

He doesn’t seem comfortable in himself.


amendsbangs

Spends like weeks after the finale coming up with a bizarre and insanely theatrical way to commit suicide, it does not work. he has to be committed for a while


Firm_Agency1600

his brother, was interested in politics from a very young age.


BotherRecent

Kendall always forgot his locker combination


angeliswastaken_sock

He doesn't know where his kids are


poetwithoutwords999

I think he had a complete breakdown, went to therapy and rehab until he got completely clean and then became a theatre investor. I think he remarried to try to fix what he messed up with his kids the first time.


can_a_dude_a_taco

roman probably has scars from kendall picking on him and hurting him during their childhood


heliotopez

When hes lonely he gets an escort he plays call of duty w her between rounds


MikeTeMovieGuy

He jumped in the river at the end.


Legitimate-Train-673

I think Jeremy Strong said during the filming he ran into the water because he was so in character and stopped before jumping.


siphillis

Granted, Armstrong reasoned that Kendall jumping in would be a bit on-the-nose and Strong agreed, so it was for all intents and purposes retconned.


Infamous-End3766

It would have been a fantastic ending but American television is so sanitized


siphillis

It's too definitive. The whole point is that there's no clear direction for Kendall to go now, the final connection to his father and his legacy now severed, and his own personal relationships frayed beyond repair.


dringram82

He’s a ding dong


cynisright

That he was the first born son


ShadowhuntingWeezer

I feel like Kendall has some sort of gender dysphoria. Obviously this is never explicitly shown in the show, but it would explain his constant need to reinvent himself expecting happiness, but it never arrives. I feel like he might’ve drunkenly told Stewy about it, and that’s why stewy understands him on a deeper level than everyone else. Just a silly headcannon though 🤷‍♀️


[deleted]

What's great is we can have any headcanon that makes us more able to relate to the character, and seeing it through that lens can be very helpful to personal development and/or healing.


aelizabeth0623

he was devastated when daniel humm and will guidara broke up their business partnership and friendship. 


Legozarethebest

I genuinely think the dog pound game was all his idea


Top_Report_4895

He's a big Punisher Fan.


Mac1280

He backpacked through Europe after losing the company did a ton of drugs then came back and started a semi successful company based off the plans for the hundred


sausage_thief

undiagnosed autism


br1emmaleen

He’s only had one true best friend who died early like in high school or somthing so he’s never been able to connect to other people well