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Milton Bobbit” is the eighteenth episode of Season 1 of The Blacklist and the eighteenth episode overall. It originally aired on March 31, 2014 on NBC.


Liz and Red are secretly spying on Tom Keen, they are working out the connection between him, his brother, Lucy Brooks and who's employing them.

Tom tries to keep Lizzie close by asking her to renew her vows. She contacts their friends and Tom's brother Craig for the ceremony. Tom acts like he is surprised by Craig turning up and whilst upstairs shaving lets on that Craig had called earlier to warn him, Craig also states Lizzie is becoming too suspicious by asking him about their dead parents.... Whilst they are having this chat Lizzie has hidden a champagne glass that Craig drank out of to send off for fingerprints and DNA analysis. The analysis comes back as a Christopher Maly, unrelated to Tom. Lizzie follows him into his hotel room and handcuffs him to the sink in the bathroom. Red turns up to ask more questions, he refuses to answer so Red takes him to an art gallery and Dembe wheels his mother around in the distance to scare him. They return to the hotel room, where Tom calls Craig, he pretends everything is fine and that he needs 2 hours and will ring him back, Tom states that he is worried about the wrath of Milos Kirchoff. Red and Lizzie then ask about Milos Kirchoff, Craig refuses to answer and jumps out the hotel window.

Lizzie looks through the tapes that the apple man was recording of her and Tom in their house. She notices that Tom hid a key under a lamp in the house, she makes a copy of the key and puts it back where she found it. As she turns around Tom is there, who may have seen her moving the lamp back, as she goes to walk away Tom puts his hand on her shoulder and says they are newlyweds to which they kiss begrudgingly to Lizzie, after she has found out he is hiding a lot more than she thought.

The Blacklist case is about a man with diabetes who was put on a clinical drug trial that is making him ill and has killed others, known as the Undertaker (real name Milton Bobbit). He is a life insurance claims advisor who speaks to people that have had their insurances cancelled due to life threatening illnesses. He offers them money that will in turn help their loved ones with all money troubles, to get this money they have to agree to a murder-suicide. The Undertaker chooses the targets, wires them the money and they kill them. The Undertaker takes the doctor who headed up the trial to the cemetery and shows him the affect the trial has had on him. The Undertaker is strapped with a bomb, Ressler manages to arrest the doctor and remove him from the situation before Milton Bobbit sets the bomb off and kills himself.

Press Release[]

“THE UNDERTAKER” SELLS THE PERFECT MURDER – Red and the team are on the hunt for “The Undertaker” – a life insurance claim adjuster who convinces ordinary people to become contract killers. Meanwhile, Liz works with Red to uncover Tom's secrets.

Number on The Blacklist[]

  • 135

Unanswered Questions[]

  1. How long can Raymond Reddington and Elizabeth Keen maintain their secret investigation? In “The Cyprus AgencyHarold Cooper made it clear that the task force overrides personal lives.
    1. A: Red is the linchpin of the task force, without him it would not exist. In “Frederick Barnes”, Liz avoided suspension because Red will only give information to her.
    2. Q: The task force sort of existed before him, Ressler hunted him in numerous nations. Cooper might attempt to control Liz to avoid giving Red more leverage. Even if he fails, his actions might alert Tom Keen's employers or worry Alan Fitch. That is incentive to give Cooper some information. Consider the anger he showed to Special Agent Walter Gary Martin when ordered to end the investigation concerning Diane Fowler in “Madeline Pratt”.
    3. A: Cooper's anger towards Walter Gary Martin came from his dislike of being overruled. While the task force to capture Red existed while he was “on the run”, there were several changes in its composition and leadership. Cooper now has exclusive control, with the consequent rise in profile as evidenced by Tom Connolly's statements in “The Judge”. He is able to close important cases that were unknown to the FBI, such as Floriana Campo and Owen Mallory.
  2. To what degree is Liz willing to accept Red's tactics and strategy? After Christopher Maly committed suicide she acted like an FBI agent, but soon realized that she needed to leave before the police arrived.
  3. Why are Liz and Red not including the task force in the investigation of Tom? Certain members, such as Meera, can be trusted to stay silent. Liz went to Aram for help in “Ivan”.
    1. A: Red does not want Tom to know that he and Liz are on to him. They could allow Meera and Aram to get involved as they can be trusted to remain silent.
    2. Q: How can including the task force alert Tom? They know the importance of secrecy. Red can say that Tom is working for the people who hired Anslo Garrick.
  4. Who was Red looking for on the list of Milton Bobbit's victims? Was it related to Stanley R. Kornish or Eric Trettel?
  5. How many of Bobbit's client’s will be arrested? Aram Mojtabai and Meera Malik did not give much hope to tracing the currency transfers.
  6. Where did Bobbit get the money for the drug test assassinations? They were his personal contract killings.
    1. A: Either by extorting his previous clients, or he has been saving his fees from past assassinations for the purpose of paying for those assassinations. Indeed he could have started his whole business for the purpose of funding the assassinations.
  7. How likely is it that “Berlin” is a person's name or codename unaffiliated with the city?
    1. A: The leaders are likely located in Berlin, Germany. This is similar to a person saying: “I am the person that Whitehall/Downing Street will scream at about the financial loss”; or “The Pentagon/White House will demand my general's stars for this disaster”; or “I am the person who is accountable to the National People's Congress/Beijing regarding diplomatic failures”; or “the Élysée Palace/French Parliament need that cryptography system.”
    2. A: It could be a code name for the contractor.
  8. Will Red be able to trace the key? Liz made a copy for her board.
    1. A: Tom told Liz what the key was for in “The Pavlovich Brothers”.
  9. Why did Red miss the key that Tom Keen placed in the lamp? He stated that he had reviewed the DVD disc.
    1. A: Tom suspected Red was on to him and hid the keys in the lamp intentionally, by screwing the bottom tight to make it look like he was trying to repair it.
    2. A: Red told Liz that he only watched “some... enough”, so he most probably missed the key scene, pun intended.
  10. How many agents did Milos Kirchoff send to watch Elizabeth Keen?
    1. A: A few, including Lucy Brooks and Maly, to make sure Tom is not compromised and learn more about Liz's connections to Red.
  11. Why was Keen chosen by Red? Does Milos Kirchoff know of her real connection to Raymond Reddington?
    1. A: Most probably, yes. Milos Kirchoff should be something totally different from Alan Fitch and they could be even linked to the events in Liz's past and Red's decision to desert from the U.S. military.
  12. Does Tom truly believe that Liz is still clueless or was it an act to maintain dominance over Christopher Maly?
    1. A: Tom is confident Liz does not know anything, but Maly suspected she knew more and warned him to be careful.
  13. Why did Red travel to El Salvador for the DNA test on the glass? Were not there any other experts?
    1. A: As Red has not rejoined the Task Force, he is able to use the people in his contacts in El Salvador to trace the DNA to Maly.
  14. What will be the aftermath of Maly's death, he jumped while wearing handcuffs? Tom said that Maly had left the city, is he confident that the police will not identify the body?
  15. Why did Christopher Maly commit suicide? Does he fear Milos Kirchoff's wrath?
    1. A: Maly committed suicide because he feared Milos Kirchoff was going to kill him if he told Red and Liz what they needed to know about Tom.
    2. Q: How is suicide superior to assassination? Death is the final result.
    3. A: It is not normal to torture yourself to death.
    4. A: It may have been to protect his family from Milos Kirchoff's retribution.
    5. A: Death before dishonor. In “Burn Notice”, “Honor Harrington”, and “James Bond”; several characters commit suicide and/or panic when confronted with the option of being arrested or failure. They fear a show trial, their families will be killed as an example, and/or their clients will seek to assassinate them before they can testify in court.
  16. Why did Dembe Zuma ask about the color of the paint?
    1. A: He saw the same color somewhere else, possibly in the house Red bought and burned at the end of “Frederick Barnes”.
  17. How was Bobbit able to coordinate global assassinations from a single office?
    1. A: By using the internet and taking weekend breaks for face-to-face meetings.
  18. Why did Milton Bobbit need ultraviolet light to stay alive?
    1. A: The rigging of the drug treatment for his diabetes left Bobbit significantly scarred and needed the ultraviolet light to keep him alive. UV could be used to fight the infection in open wounds.
  19. Why did the window break so easily? Hotel/motel window glass is stronger than that.
    1. A: Artistic license
  20. Why did the taxi explode? Crashing a car does not cause the petroleum to explode. Did Wahid Davi rig the engine?
    1. A: He probably rigged the cab to ensure success. As a professional driver he would know that people can walk away from horrific car accidents.
    2. Q: This would raise suspicion, the police would know that ramming does not cause an explosion.
    3. A: Then the murder/suicide theory coupled with mental instability becomes the primary theory.
  21. How was Danny Moss going to complete his murder/suicide and make it look like an accident caused by mental instability?
    1. A: He was probably planning suicide by cop and could have left incoherent ramblings on his home computer. The people Bobbit hired had mental problems.
  22. Why did Bobbit's bomb produce no flames in the explosion?
    1. A: Explosives produce heat, if the flash point of the bomb materials and his clothing was above the temperature produced by the explosion, there would be no fire.
    2. Q: Why was Donald Ressler not injured by the explosion? Even without the flames, there was shrapnel and a shockwave.
  23. Was Mitchell Travers arrested?
    1. A: Most probably yes. Travers was involved in rigging the drug trials.
  24. How did Bobbit learn that the drug trials had been conducted with forged evidence and illegal methods?
    1. A: He was the first patient who tried the drug to treat his type 2 diabetes and got scarred significantly, including having to use a prosthetic nose to appear normal. Bobbit wanted revenge for Frederick Osborne and Travers' involvement in the rigging the drug trials that lead to his current appearance.
  25. How did the FBI learn that the drug trials had been conducted with forged evidence and illegal methods?

Slanders on the FBI and FDA[]

  1. Why did only Liz and Ressler go to the rally, and not involve the local police and/or event security? They could also have brought a FBI SWAT team.
    1. A: There appeared to be no event security.
  2. Why did the FBI not have Danny Moss describe Bobbit to a police artist?
  3. Why did the Food and Drug Administration not take action after Bobbit got sick? There is a difference between approving a rush job and ignoring patients who suffer from faulty drugs. Consider the investigations that occur when automobiles are discovered to use faulty parts. Another example is when corporate scandals and corporate fraud occur, the U.S. Securities and Exchange Commission is questioned why they ignored the warning signs. Why did Frederick Osborn and the others rig the drug trials? If the drug was useless, then the truth would have come out after other patients got sick.
    1. A: They needed the funding and were told by Travers to rig the trials in order to convince the public diagnosed with diabetes and other illnesses that the drug works.
    2. A: General Motors are currently trying to explain why they allowed their cars to kill people for the past 10 years. The real FBI are investigating whether they committed bankruptcy fraud, by going into bankruptcy (which protects the company from law suits) relating to the early years of this issue. The National Highway Traffic Safety Administration is claiming that General Motors hid the results of their internal tests, which is why they did not order a recall. As General Motors have just proved, bankruptcy protects from lawsuits.
    3. A: The FDA relies on drug companies and individual physicians to report problems. It does not investigate rumors, or unsubstantiated allegations.
    4. Q: Some doctors and many patients would complain to the FDA and media after they realized the drug had failed.
    5. Q: The truth about the drug's uselessness would eventually be known. That would result in lawsuits and criminal prosecution. The risk does not seem worth the reward.
    6. A: As General Motors have just proved, bankruptcy protects from lawsuits.
    7. A: Patient complaints tend to be ignored unless they are phrased in the correct medical legal language. Individual physicians complaints can be categorized under several different headings, without their similarity being noticed.


  • Frederick Osborn FBI file
    • Last Name: Osborn
    • First Name: Frederick
    • Home Address: 7654 Colony Rd, Fairfax, VA 22030
    • Nationality: USA
    • Date of Birth: 05-08-1942 (8 May 1942)
    • Place of Birth: Alexandria, VA
    • Sex: Male
    • Height: 5'-10"
    • Weight: 190 LBS
    • Eye Color: Green
    • Hair Color: White/Gray/Grey
    • Marital Status: Widower
    • Spouse: Osborn, Ethel
    • Children:
      • Osborn, Matthew
      • Osborn, Melinda
      • Osborn, Michael
    • Unkown heading
      • MA Business Administration
      • Venture Capitalist


Main star[]

Guest star[]


  • Angela Reed as Anna Mitchell
  • Kiran Merchant as Wahid Davi
  • Elena Hurst as Dee Torres
  • Jeff Lamarre as Sen. Bennett Cochran
  • Martha Karl as Mrs. Sutton
  • James Riordan as Ian Wright
  • Anthony Fazio as Jared
  • Sam Freed as Frederick Osborn
  • Samantha Posey as Assistant (Bosnia)
  • Kathleen Peirce as Craig's Mother



External Links[]

Season 1 Episodes
 · Pilot  · The Freelancer  · Wujing  · The Stewmaker  · The Courier  · Gina Zanetakos  · Frederick Barnes  · General Ludd  · Anslo Garrick  · Anslo Garrick: Conclusion  · The Good Samaritan  · The Alchemist  · The Cyprus Agency  · Madeline Pratt  · The Judge  · Mako Tanida  · Ivan  · Milton Bobbit  · The Pavlovich Brothers  · The Kingmaker  · Berlin  · Berlin: Conclusion  ·