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Whiskey Cavalier - Confessions of a Dangerous Mind - Review: Merry SHEP

Because the holidays are their busiest time, Team Whiskey is celebrating Christmas in the off-season. It’s a Supplemental Holiday for Espionage Professionals (SHEP). It’s festive and fun and there’s a workplace Secret Santa. THIS SHOW AND ITS TROPES.
Who’s in charge of the Secret Santa? That would be Jai, because Susan suggested he could try making friends.

Tina’s off to Miami to seduce some playboy billionaire for bank codes – much to Standish’s dismay. She’s casual about it but this is new for Standish. He doesn’t know how to process news like this. He isn’t used to his girlfriends having jobs like this. He turns to Frankie for some comforting advice – which isn’t really in Frankie’s wheelhouse. After telling Standish sometimes real sex is needed to sell a cover, she asks Susan if that response was too mean. Because like Standish is working on keeping a romantic relationship healthy in unconventional circumstances, Frankie’s still working on being a comforting friend.

Over a game of pool, Will tells Frankie that if a relationship stands a chance you have to trust that person completely. This is interesting. We assume he trusted Gigi completely, and look at how big of a mistake that was. He struggled with trust after that, which we saw in Five Spies and a Baby when Frankie had to remind Will that phoning/texting Emma only made it look like he didn’t trust her. He certainly didn’t trust Frankie at first and made that very clear. “No one trusts anyone completely,” Frankie tells him, to which Will replies, “I trust you completely,” and being that it’s coming from Will it’s actually true. Will’s such a cinnamon roll that once you do have his trust you have it completely (until you hook up with his girlfriend). How did this man become a spy again?

It’s suddenly obvious how Gigi and Ray had an affair behind Will’s back for seven months. As Frankie puts forth a scenario where, married to Will, he comes home to find her in a nightgown and a man in the bathtub, Will only sees rational explanations for everything.
Oh, Will, sweetie.
He likely saw the signs Gigi was cheating on him but convinced himself otherwise.
Ray walks in as Will and Frankie are discussing their hypothetical marriage and catches the tail-end of the conversation.
“I never know what’s going on,” Ray laments.
No. You don’t. Because no one trusts you anymore. You’ve got some things to work on.
And you know what? He does work on that this episode.

Standish does exactly what Frankie told Will not to do two episodes ago. He leaves a very awkward voicemail for Tina because he’s freaking out over her Miami trip. This time it’s Frankie’s fault the call happens. She planted extra seeds of doubt in Standish’s head. Not because she wants to sabotage relationships, but because creating chaos is fun. And while her smile in response to being caught out is somewhat satisfied it’s also a bit guilty. She loves the mayhem, she can’t help it, but she IS working on being more comforting. We’ve seen it multiple times.

Meanwhile The Trust might be planning something big so the team’s off to Europe to babysit a prisoner who’s being transported for interrogation. The prisoner turns out to be Ollerman – Will’s ex-boss who shot Ray and pulled out Standish’s tooth in the pilot episode. Neither Ray nor Standish are going to forget those events any time soon.
The transporting of Ollerman doesn’t go to plan when a car in the convoy is taken out by an explosive and a masked sniper turns up. But Team Whiskey gets the job done.

Remember how hurt Will was by Ray and Gigi’s betrayal? That didn’t stop Will from sitting at Ray’s bedside after Ollerman shot him. Will might have the biggest heart on TV right now. What Ray did was terrible and no one’s arguing that, but maybe it’s forgivable if you’re Will? After Ray is made to suffer through a few friend-less months, works his butt off and redeems himself for his behavior, that is.

Ollerman thinks he’s going to tear Team Whiskey apart, and he gives it a pretty decent try. He’s quick to get into their heads while they try to interrogate him.
During this it’s revealed that after their first meeting Will reported Frankie as dangerously unstable and potentially disloyal. He comments on Jai’s struggle to connect with teammates - words written by Susan. And brings up Tina’s current Miami mission while planting more seeds of doubt about the longevity of the relationship in Standish’s head.
His final shot is another aimed at destabilizing Will and Frankie. She asked for permission to take Will out during their first mission, a plan which likely changed around the point she was shot. She had clearance to tie up loose ends. One of those loose ends was Will. He’s not thrilled to hear this but even when cracks begin to show in the team from Ollerman’s words Will remains the voice of reason.

Will: “Do I wish that Frankie hadn’t planned my assassination? Of course I do, who wouldn’t? But I’m not going to sit here and let it dwell on me.”
Frankie: “No, because it was Moscow, it was winter, and we were all cranky.”
Will: “Eventually I’m going to need a better explanation than that.”

Will shouldn’t be too worried moving forward though. Wanting to kill someone – but ultimately NOT killing them – is kind of how Frankie makes friends. It’s what happened with her and Jai, and they’re besties now. This is a good thing. Really.

Todd continues to be cold and emotionless. There isn’t a single second Todd’s been onscreen where he’s been nice. So, when he turns out to be working with Ollerman it really isn’t a surprise. Some people are just bad people. And some are just good – and I’m mentioning that because maybe Emma’s one of those good people? She’s not even in the episode and an obviously awful person has me thinking there might be just pure good in her and the writers are just trying to throw me off with her engraved watch after 6 days of dating gift-giving. I’M SO TORN ON EMMA. See more on this in my final thought.

Despite the team’s best efforts to keep the news of Ollerman’s arrival from Ray, Todd tells Ray. Ray’s anger gets the best of him when confronting Ollerman and he gets in one good punch and a couple of kicks. This undoes a lot of Will and Frankie’s work.
While trying to hack the phone system to delete his voicemail to Tina, Standish finds a breach in the firewall. Susan is taken by one of Ollerman’s goons and the Todd reveal happens.

It’s when Jai isn’t overthinking it – like he did during the Christmas party – that he actually makes real connections. When Ray is anxious over Susan being taken, Jai reaches out to stop his nervous hand tapping and calm him down. Jai isn’t as bad at this as he thinks he is. Not anymore anyway.

Frankie and Will devise a plan to make Ollerman think Frankie has switched sides. Will assures Frankie he trusts her – and Will wouldn’t say it if he didn’t mean it.
To convince Ollerman she has turned, Frankie shoots Will. First in the leg, and then in what appears to be a kill shot in his torso. But Frankie hasn’t turned. The first shot, in his leg, is a through and through. The second, in his side, is just a graze. Frankie’s got great aim.
Ollerman knows Frankie hasn’t turned. “You can’t hide how much you care about him,” he tells her in reference to Will. And it’s true. Frankie’s a good liar, but not when it comes to keeping these long forgotten emotions from showing on her face.
Ollerman gets away, but Team Whiskey will get him. I smell a finale confrontation.
Ray and Jai, meanwhile, take Todd and his buddies out and save Susan. It’s a big moment for Ray, who proves he is capable despite Ollerman’s words in the pilot about only keeping Ray around because he’s an idiot.
Susan may not have gotten Ray a Secret Santa gift, but her telling him he did great is a better gift than any she could have bought/found around the office. It’s a boost for his confidence and another step towards becoming part of Team Whiskey.

Back at The Dead Drop Will raises a glass to the team. The whole team, which Ray is included in when Susan beckons him over. Afterwards, at Susan’s prodding, Will tells Ray he did good and pats his shoulder. Ray’s thrilled reaction might be the cutest scene ever and I’m warming to him. He just wants to be liked. He just wants his best friend back. If he gets both of those I can’t see him ever being stupid enough to hurt Will again. He understands the repercussions now.

Jai and Standish exchange Secret Santa gifs – and because Jai is building connections and making friends the two even do the most awkwardly adorable chest bump ever.

Fans of FieryWhiskey (which is cute but personally I think Friskey is more fun as a couple name) had their fingers crossed there would be a Secret Santa moment between the two and are not let down. Will’s gift to Frankie is the bullet she shot him with, which is kind of Will’s thing. It’s strangely adorable and Frankie appreciates the gift too. Hopefully we’ll see it around her neck in a future episode.

One final thought: Who was the person/sniper who earlier took the gun and later had it pointed at Frankie as she and Will confronted Ollerman? Who is this mysterious person in a hood with gloves? Because keeping their identity a secret during the sniper scene I get, but still keeping it a secret at the end of the episode is suspicious. That suggests to me they’re someone we already know.
So, could it be Emma? Or Tina (who was on another mission the entirety of this episode, and Ollerman knew where she supposedly was)? It does feel like one of these women is trying to infiltrate the team. TV has made me too suspicious (looking at you, Timeless writers and Jessica Logan).

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