It’s a week of mergers on The Blacklist, and “Alistair Pitt†is here to arrange the impossible. We start the episode with a shootout in a restaurant. One mobster killed another in a rival family, and all hell is about to break loose. In comes Alistair Pitt to save the day. If the killing doesn’t stop, there will be nothing left of these families or their businesses.
While the family is watching over their son, who is now comatose, Alistair Pitt comes to propose his solution to the mob family’s problems. The two rival families are only killing each other while their businesses crumble. Pitt recommends arranging a marriage of the youngest daughter of one family with the youngest son of the other. While both families seem disgusted by this suggestion, eventually, they relent.
When bringing this case to the FBI, Red describes the matchmaker as “a man who brings together warring crime families through mutual self interest, leverage, or violence if necessary.†And violence there was. The youngest son would not agree to the marriage since he was already in love with another. So the family gunned her down in cold blood. In the end, the one mob family doesn’t seem to agree with the merger and tries to gun down the other family. The FBI intervenes, but Reddington takes off with Alistair Pitt.

Raymond Reddington has a particularly sordid history with our matchmaker. During the episode, we saw multiple flashbacks of Red dining with a lovely woman, Josephine. Red gives her glass animals for her collection just before she says that she is getting married. Red asks if she loves her husband to be, and she says that she loves Red. He sees her turn her wrist over, and there was a bruise. Clearly her fiance is not a good man, and Raymond is not happy to say the least. Josephine refuses to ask for his help, so Red doesn’t seem to do anything.
Later, Red gets a frantic call from Josephine. She says, “He knows about us.†And, she is clearly scared for her life. By the time Red shows up, Josephine is beaten and barely alive, but Red kills her fiance and gets her to safety. Red recounts this story to Alistair Pitt, explaining that Pitt arranged that marriage. Their parents were from rival crime families, and the marriage was the only way to guarantee peace and profit for all. Red says, “You destroyed a creature more beautiful than you could ever comprehend,†before he murders the matchmaker. Red goes to visit an extremely disabled Josephine to tell her, “It’s done.â€

Meanwhile, Liz is still set on adoption for her unborn child. She goes to the adoption agency where she and Tom were going to adopt way back when. She explains that she wants an open adoption, a chance for her to be in her child’s life. The agency finds a great couple, but they back out when they realize that she is “that Elizabeth Keen.†The agency recommends that the only way to get her baby adopted is to have a closed adoption. Of course, Tom still has no idea that she is considering any of this.
Speaking of Tom, it seems that he is up to no good this week. His old girlfriend, Gina, is back in town. He asks her for a job. It looks like Tom wants to get enough money for Liz, himself, and their baby to run away and live comfortably forever. Tom poses as the FBI to “catch†Gina robbing a jeweler. He asks for help from the owner to interrogate Gina, but instead, they knock him out and take everything he’s got. I guess Tom is getting back into the crime business after Red stopped his legitimate job in Boston from ever materializing. I’m not sure this is the right path for Tom to take for their family.