Season 3 Episode 13
The task force goes after a negotiator who's uniting two crime families; Tom reunites with a dangerous former flame. Tony Shalhoub guest stars.
As tensions escalate between two warring criminal families, a mysterious man offers to broker a marriage between them in the hope of creating peace. Red (James Spader) suspects the Promnestria (Tony Shalhoub), a negotiator who facilitates mergers between criminal enterprises and gets a percentage in return. Now the Promnestria plans to unite the Erikssons and Vacarros; if the two families merge, they'll rival the Mexican cartels for control of drug trafficking on the East Coast. After the task force obtains surveillance photos of the Promnestria, Red uses his network of hotel maids, waiters and valets to track him down and determines his identity to be Alistair Pitt, corporate consultant. Red then secures an invitation to the upcoming get-together between the families, where it turns out the Vacarros plan a mass slaughter of the Erikssons. Red leads the task force to the celebration, which quickly turns into a massacre. Amid the crossfire, in which members of both families are killed, Red leaves the scene with Pitt. We learn that several years ago, Pitt arranged a marriage between the children of rival arms dealers Stockwell and Moliere. Red was in love with Josephine Moliere, and she was forced to marry the only Stockwell son, who happened to be unstable and violent. He savagely beat Josephine, and Red spent years seeking revenge on Pitt. Finally able to avenge Josephine, Red shoots and kills Pitt, then visits Josephine - now in a convalescent facility - to let her know the deed is done.
Meanwhile, Tom (Ryan Eggold) contacts former girlfriend (?) and corporate terrorist Gina Zanetakos, hoping for additional income. She offers him a cut of her gem robbery operation. Though it appears to be a suicide mission, they bypass intense security and pull off the multi-million-dollar scheme. Meanwhile, Liz (Megan Boone) works with an adoption agency to find parents for their unborn child - without Tom's knowledge. A couple shows interest, but once they realize who she is, they insist on a closed adoption, meaning Liz will never have any contact with her child.