The Company You Keep Season 1 Episode 1 Review: Pilot

Milo Ventimiglia returns to the screen on The Company You Keep Season 1 Episode 1, “Pilot,” for a role that’s quite different from Jack Pearson.

Now, Ventimiglia plays Charlie, a skilled con man who winds up falling for a CIA agent after getting played by his fiance — and having his heart shattered when he realizes she was never who she said she was.

In fact, it’s Charlie’s heart that may be his biggest downfall. This guy is a romantic who is only a con man because that’s the family business. Plus, he’s good at it. Really good. 

The pilot episode has everything: elaborate cons, romance, suspense, and even a bit of humor. It’s great fun all around, and the cast already has great chemistry. 

ABC has tried shows with a similar tone and similar concepts to this one in the past, none of which managed to stick the landing. The Company You Keep, however, has a bit more substance and heart, which is ultimately what I think will keep viewers coming back for more. 

The first few moments of the episode grab our attention without missing a beat, from Charlie’s card tricks in the mirror to a con showing how their family works together masterfully. Every detail is planned perfectly. Charlie’s sister, Birdie, watches from afar and has Charlie’s ear.

Charlie puts on the charm in an act that’s just about perfect, and then, at just the right time, Charlie’s father and fiance come bursting in pretending to be FBI agents. As all of this happens, we quickly learn a little about what each character is like, and it sets the tone perfectly.

There’s just one problem with this perfect con, though. Charlie’s fiance, played by Bridget Regan, has no plans of sticking around. She takes the money for herself in exchange for her engagement ring, playing Charlie for a fool.

And when Charlie realizes it, he’s shattered. Not only is he heartbroken by her actions, but it’s cost his family money they desperately needed. 

Based on his family’s reactions, it’s clear this is a man who is too easily blinded by love — a trait that makes his character all the more likable. 

It’s fitting, then, that he winds up in a similar situation shortly thereafter. 

Charlie and Emma have an instant connection at a bar, but both are clear they have baggage and that they don’t want to say much about who they really are. Their banter is believable and endearing, and it leads to a three-day escape in a hotel room, where they both just enjoy each others’ company and forget about their real lives together. 

It’s not all about sex, either. It’s about eating great food, having fun, relaxing, and making each other laugh. Their interactions feel authentic, and it’s easy to understand why they hide out together the way they do. 

Emma is also a great match for Charlie. She’s smart, and she knows how to read people. In fact, what’s really interesting is that they both have similar skills, but they use them in such different ways. Charlie, running cons, and Emma, working undercover for the CIA.

There’s just so much potential here.

And of course, once the two of them have to get back to real life, they wind up running right back into each other. While Charlie and his family attempt yet another elaborate con — this time on a TV preacher who deserves everything he gets — Emma is working a case that puts her right next to him. 

Perhaps my only gripe with how this all unfolds is that Charlie tries the classic move of pretending Emma means nothing to him because he thinks it’s best for them not to get involved. It’s patronizing, and it’s a ploy that’s used way too often. 

The con goes well, and it’s an important win for Charlie and his family. This is where I think the series really sets itself apart. Charlie, Birdie, and their parents have worked together for a long time, and Charlie is ready to take over the “family business” so that his parents can retire.

We also learn that Charlie’s dad is suffering from memory loss, and that it’s only going to be getting worse.

There are real stakes for this family — and they also don’t want to run cons forever. They want this latest big one to be the last one. And that makes even more sense considering there’s a child involved. We’ve only seen a little of Birdie’s daughter, who is deaf, and extremely perceptive.

Being able to walk away from this life of crime would be a good thing for all of them. 

Unfortunately, that’s not going to be able to happen so easily. Emma has been investigating the crew that we met at the top of the episode, and while most of them do get arrested, the woman who is the brains of the operation makes it out. 

And she heads right to the bar to threaten the family and demand the money back that was lost. That means the family isn’t going to be able to stop running cons after all, at least not for a long time. 

Ending the episode in this way sets us up for some great storytelling. The family element of The Company You Keep is so complex, and we’ve clearly only scratched the surface so far.

Now, the fact that they want out of it but won’t be able, all because of Charlie’s fake fiance? It makes this all so much more than just another fun story about a con man. Add the element of Emma the CIA agent, and it’s that much better.

If this first episode is any indication, The Company You Keep is going to live up to the hype, that’s for sure. 

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What did you think of this episode of The Company You Keep? Share your thoughts in the comments below!

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The Company You Keep airs Sundays at 10/9c on ABC.

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