Liz’s (Megan Boone) team chases after a man who coerces people into committing murder-suicides in the newest Blacklist. Nicknamed “The Undertaker,” Milton Bobbit (Damian Young) finds terminally ill patients through their canceled life insurance policies with his company, offering financial security for their loved ones if they carry out his dirty work. His targets are people connected to a series of failed clinical trials that made him and others terminally ill—doctors, financiers, etc. Ready to end his own life, he pursues his last target by himself.
Elsewhere, Liz finally joins Red’s (James Spader) spy operation on Tom (Ryan Eggold), starting with his fake brother. After Tom tells her that he wants to renew their wedding vows, Liz invites Craig to fly in from Chicago and wed them at their house. When he arrives, Craig reveals to Tom that he thinks Liz is onto them, which Tom quickly dismisses. Red figures out Craig’s true identity after lifting his DNA from a wine glass that Liz gave him at the ceremony. She tracks him down in his hotel room and, after a lopsided fight, handcuffs him to the bathroom sink. However, before Liz and Red can get much more than his real name (Christopher) and the word “Berlin,” he jumps out the window, killing himself.
The show’s episodic plot left some questions unanswered. For instance, where exactly was Milton getting the money to pay off these people? Even as an employee at the insurance company, there’s nothing to suggest he has the connections or influence to make sure that they are taken care of. Odds are he could not make it happen by himself. While it delivers a clear motive, as just about all of the Blacklist villains have, Milton’s only about a halfway sympathetic figure. His appearance and suffering can tug at the heart strings, but at the end of the day, he still manipulates dying people into committing his crimes. Though none of the show’s criminals are ever justified in their actions, his method is a little tougher to swallow than the others.
On the other hand, Liz and Red’s spy game with Tom has consistently become the more interesting storyline in recent episodes. Liz’s character has finally shed her naïveté and become the aggressor with Red’s help. For the first time in a while, she outsmarts Tom by using his own proposal as a way to dig into his cover. Although it seems like someone with Red’s experience would have seen Craig’s pirouette out the window coming, his death allows the search for information on Tom to continue even longer. Liz’s most difficult challenge clearly won’t be the investigation but the ability to avoid tipping off Tom with her behavior.
Additionally, this episode got back to one of the show’s original hooks: Red’s snarky and arrogant sense of humor. Upon entering the hotel room, he remarks to his henchman Dembe that they may need to carry Craig out in pieces. After seeing his horrified expression, Red laughs and says he is only kidding. Also, while asking a scientist in El Salvador to help him identify Craig, the scientist reveals that Red had an affair with his wife. Rather than offer a sincere apology, Red argues that he’s better off without her. To end the episode, Red is once again dismissive of Agent Cooper (Harry Lennix), ignoring his question about the Milton Bobbit case as he exits.
While the weekly procedural may disappoint from time to time, The Blacklist will still be able to engage the audience through the serial plot. Liz, Red, and Tom are clearly the three most interesting characters at this point, and the stakes are significantly higher for them in this storyline.