Red makes a personal connection, with heartbreaking results.
The Blacklist - Season 2

Over the course of eight seasons, The Blacklist has run me through the full range of emotions — excited, scared, giddy, anxious, thrilled — and more secondhand embarrassment than modern arithmetic could possibly quantify. But I don't know if an episode of The Blacklist has every made me feel quite as heartbroken as I did watching Reddington get to know Anne — who I've mentally been referring to as "lovely, lovely Anne," partly because of Parks and Recreation but mostly because her character is such a welcome presence among these otherwise notorious knuckleheads — only to realize that his desire to see her again couldn't outweigh his need to protect her from himself.

Of course, this is far from the first time The Blacklist has dipped its toes into romantic disappointment. The Post Office gang have gone through their fair share of heartbreak over the seasons, but I've built up a tolerance to that; I expect most of their significant others to reveal themselves to be spies, or to die untimely deaths, or more often, both. Reddington, however? We've never really seen him get romantic with anyone, let alone get hurt. 

And according to Dembe's best-friend-check-in right after Reddington drank half a bottle of wine and started planning what kind of engagement ring he was going to get Anne… that kind of detachment has been intentional. With his life in turmoil right now, Reddington is craving comfort — but the world he's created around himself is not a comfortable one. Personal relationships make Reddington and the people he cares about vulnerable to those who would seek to hurt him. We've seen Red's care for Dembe and Liz be weaponized against him numerous times, and his budding bromance with Cooper becomes more and more dangerous every day.

But hey, if Cooper and Reddington can't have "ordinary lives" with ordinary aspirations (advancing a career and having a girlfriend, respectively), I'm glad these two can at least have each other to constantly reconvince themselves that what they're doing is for the greater good, and therefore worth it. Let's see how the greater good is being served in this episode.


The first thing you might notice about this Blacklister is: That's a high number! We've been wading around in the mid-100s all season long (y'know, excluding numero uno, Lizzie Keen, whose Blacklister antics are completely on the back burner this episode), but now it's time to get down with a bona fide sub-100 baddie. Ogden Greeley is a defense contractor for the National Reconnaissance Office who disappeared five days ago. He designed much of the software that controls the United States' satellites, which much of the country's national defense is dependent upon.

And he disappeared five days ago.

At first, the National Reconnaissance Office thought Greeley's disappearance could be an act of war, given that his knowledge of the United States' national security defenses would be detrimental in enemy hands. But then Reddington shows Cooper a video of Greeley that's been circulating in the criminal community in which Greeley says he's "tried and failed to convince those charged with keeping America safe to act responsibility, and as a result, I have come to believe that the only way to address our security issues is to exploit them." 

Oh, great — a treasonous terrorist masquerading as a patriot. How fun! Greeley finishes the video by announcing that he's decided to sell his knowledge of the vulnerabilities present in the very satellite system he helped design to whoever offers him the most money in the next 24 hours, giving that buyer the power to thrust the entire U.S. military into chaos.

The Blacklist
Credit: Will Hart/NBC

And if you can believe it, Greeley's plan to sell America's national security to the highest bidder isn't as altruistic as he makes it out to be in his little video. When Park and Ressler visit his wife, she tells them that Ogden is a good man who would never betray his country or his family unless he was forced to do so. But in the very next scene, we see him carrying around the briefcase containing all his eBay-auction satellite secrets, and making out with a lady sporting a ne'er-do-well bob haircut. This guy ain't coming back to family life anytime soon.

Aram finds out the be-bobbed woman is a Russian spy named Nina Kurylenko, so Park and Cooper travel to London, where she was last seen, to interrogate her. After they chase her down, they tell her they know she was assigned to convince Greeley to betray his country, and they want to know if he's selling the intel to Russia. Kurylenko doesn't know who Greeley's highest bidder is, but she does know where he's meeting them: Ulaanbaatar, Mongolia.

With only hours before the sale is set to take place, the U.S. government can't get agents into Mongolia, and they can't tell Mongolian forces about Greeley's intel without putting national security at risk. So Cooper says they only have one option: the federal kill list.

The next thing we know, Cooper is at the White House, negotiating with the president's top military advisors over whether this is a case for the commander-in-chief to approve a drone strike. They go back and forth about whether Greeley's sale really represents an "imminent attack" that would warrant a targeted killing by the military, and whether the due process that Greeley is entitled to as an American citizen is absolute in this circumstance. In the end, the president approves a strike on Greeley and whoever the buyer he's meeting in Mongolia is. Cooper and the other advisors are in the room with cameras on Greeley, and drones are ready to strike when he comes in contact with the mystery buyer…

And then ol' Coops has to do a quick "Whoopsie-daisy, what if we actually don't kill these guys right now?" Because the buyer is Raymond Reddington.

Cooper argues that Reddington is just a regular criminal, not an enemy nation state, and therefore doesn't present an imminent threat. It's pointed out to Cooper that Reddington most likely plans to sell the technology to another country that does present an imminent threat — and that turns out to be about half-true. Because once Cooper prevents the strike and swears that he'll personally find Reddington and hold him accountable for what he did, he does indeed find Raymond Reddington… sitting in his office where they regularly meet for a cocktail.

It's revealed that Reddington's plan is indeed to sell the data to an interested country: the United States. He says he bought it for $150 million, and he'll give Cooper the friends-and-family resale rate: $175 million.

Cooper informs Reddington that he just saved his whole life from a drone strike, so he'll get him $155 million, and he'll also be taking his thank-you now, which Red happily complies with. It's quite adorable how these two are negotiating national security like they're just a couple of buds negotiating the borrowing of a lawn mower with a six-pack of beer. And speaking of adorable…

Anne. Oh, lovely Anne! Early in the episode, we see Reddington back at the spot in Central Park where he met a birdwatcher named Anne a few episodes ago (a few days ago in Blacklist time). As he's sitting on a bench, Anne arrives again, and their chemistry is as easy and comforting as it was the last time. She shows him a sketch she's made of a fox sparrow, and he asks her to take him to the area of the park where she spotted it. Along the way, they talk about her husband, who passed away, and how their shared love of musical theater is the reason she pinches her pennies to take a weeklong trip to New York City from Wichita each year. They share a chicken salad sandwich, and you guys, it is all just charming as hell.

When Anne's Uber arrives to take her to her next scheduled activity, they share a sad goodbye, after which Reddington gets on a business call. And when he hangs up — Anne is there. She's canceled her car in lieu of getting Red to help her find a souvenir for her sister. He takes her to a little chocolate shop where they share a bottle of red wine, get a little tipsy, and I think fall in love. At least I know I fell in love with the idea of Raymond and Anne falling in love. But eventually Dembe tells Red it's time to fly to Mongolia. Anne's flight leaves the next morning, but Red begs her to change it so he can take her to a Hitchcock screening the next night. He says he'll meet her outside the theater with two tickets…

But on the flight back from Mongolia, Dembe douses Reddington with some sobering reality. "I understand what she means to you, what she represents," Dembe says. "But you walked away from an ordinary life a long time ago… She'll get hurt, Raymond, and you don't want that."

Reddington doesn't want that, and so when we see Anne waiting outside the theater, it's immediately clear that he won't be showing up. He calls her to say he's sorry, and she says it's okay — she didn't change her flight, she just arrived back in Wichita. But Reddington is sitting in a car across the street, and he knows that she did. He knows that lying to yourself about the things you want most can temporarily make hard things a little easier.


  • They really found the perfect actress to play Anne (the mononymous and Tony-winning LaChanze!). She's so warm and yet chill at the same time — a perfect match for Reddington. I hope this isn't the last we see of her… but I also hope the next time we see her isn't because Liz used Red's affection for her against him. But also:
  • This man let Anne buy him dinner, got her to change her plans for him, and then didn't show up? That's some, ahem, f-‑‑‑boy Blacklister behavior.
  • I haven't mentioned Cooper's brief run as a politician just yet because I'm not sure whether it will serve a larger purpose in the Blacklist narrative. I do know that he made a few enemies after being approached to replace a retiring Virginia senator, and ultimately turned it down when he uncovered that he'd only get the retiring senator's endorsement if he agreed to vote yes on a "black budget" that would score the senator's son a $100 million contract…
  • But that same decision also got him a hell of a pep talk from Red, who reminded him that he could have just said yes to the endorsement, been sworn in, and then voted no on the budget he said he'd vote yes on. "But you didn't, because your word is your bond — very few people can say that."
  • While Cooper is at one of his fancy senator lunches, Ressler tells the Task Force he's away on personal business. "Personal business!" Park scoffs. "When we're trying to stop a war in space?!" Our girl always keeps it real — imagine if she knew Reddington was flirting around Central Park on a date right now…

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The Blacklist - Season 2
The Blacklist

James Spader is Raymond "Red" Reddington, a mastermind criminal who teams up with the FBI.

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