I have said before that Kendall is, of the Roy siblings, the most sympathetic. There’s a reason for that, and it isn’t because, as many speculate, the series is setting up Kendall to die in the end.
No, it’s more like he’s the most self-aware.
To be clear, Kendall’s self-awareness is often fleeting. It pops up here and there when he tries to do something and realizes how, well, hollow he is. Shiv, Roman, Connor, all of them are off in their own little worlds, places built by themselves since, unlike Logan, not a one of them ever had to build anything on their own in their lives. They’ve all led lives, more or less, off the largesse of their father’s success. But every so often, Kendall, the only one with kids of his own, shows some level of getting what he doesn’t have, and those are the moments when he seems like a man that can, perhaps, be a little pitied.
That’s what happens here, and at his 40th birthday party no less.
To set the stage, Kendall is throwing a massive party, inviting all kinds of people. How many of them are actually his friends? Probably none. What about his family? Logan isn’t going. That’s clear. Shiv and Roman have no intentions on going right away. Tom and Greg have reason to celebrate as it looks really unlikely either will be going to prison. Plus, Logan told Tom he’d remember Tom’s offer to do prison time. But no, none of them are planning on going. Connor might, but he’s not hanging around the Waystar offices.
But then word gets out that Kendall is getting the reclusive Lukas Matsson to attend. He’s another rich guy, this one with a hugely successful streaming service. He’s also a bit antisocial. Kendall is looking to buy him out. So is Logan. Can Roman and Shiv go to the party and try to cut a deal with the guy there? As an added bonus, he sends Roman with a “gift” for Kendall.
The gift is a buyout. Kendall looks…heartbroken to get it for lack of a better word.
Also, Roman does cut a deal with Matsson for a meeting despite Kendall’s best efforts to keep the others away from the guy. Matsson, played by Alexander Skarsgard, has some conditions, all of which Roman is happy to agree to.
But really, this is about Roy dysfunction as every episode is. Shiv is hardly comforting to Tom even now that her husband will be staying out of jail. Connor refuses to give up his coat at the door, an ongoing and very Connor-ish situation. Shiv dances like a fool who doesn’t know how. Roman is the only one who seems to be doing OK. He got the Matsson meeting and he got his name on Logan’s gift, but not Shiv’s, so she was cut out and doesn’t like that much.
Roman, dude, you will fall the same way your siblings did. Trust me, oh fictional character who cannot hear me.
But then there’s Kendall’s self-awareness. He finds his ex-wife Rava there. Waystar people are harassing her and the kids. She’s there with a new boyfriend. And she says the kids sent their father a gift in rabbit-themed paper. That should be it for Kendall. He’s starting to realize his efforts to have a big party that doesn’t look like an asshole’s party are for naught since, well, it looks just like that, and he very much is one of those things. His buzz-word loaded conversations are empty, and so is he. His demands were so random and perplexing that it helps Greg get a date out Kendall’s assistant, where even Greg more or less knows it’s to spite Kendall. However, if Kendall can get his children’s gift, he at least knows someone cares. His family doesn’t. His ex-wife has moved on. His new love interest Naomi got a gift that suggests she doesn’t really know him that well. Shiv and Roman are only there to cut a business deal. Connor won’t give up his coat. But there’s still his kids. He can maybe get something from his kids.
He can’t find their gift.
That’s his breaking point this time around. He leaves his own party, clashing with his siblings on the way out, where a triumphant Roman actually knocks Kendall to the floor. Kendall just goes home with Naomi and cries.
And that is why he’s the most sympathetic. Not because he’s a better person. He isn’t. He’s actually pretty harsh to Naomi and his siblings after he can’t find the gift from his kids. He’s just more aware how awful he is sometimes, and it hurts him.