u/Tippy345

Reddington: The only thing worse than a lie is the lie that compounds it... I know about the network, Smokey. The shipments of meth you're making to Phoenix, Miami, Seattle, Boston, and everywhere along the way. Smokey: I didn't turn you into the cops, if that's what you think. Reddington: What I think is that you're a born carny. You're a con man. You're simply hard-wired to help yourself at the expense of others. Friends, addicts, enemies, even me. In my absence, you built a network that ships meth coast-to-coast. That's impressive. Offensive... Smokey: Look, Red, you want me to dismantle it, it's dismantled. I told you, I'll do whatever you ask. Reddington: Have you ever had a flying dream?... A dream in which you suddenly have the power of flight unburdened by the weight of apprehension and doubt, you suddenly find you can fly. It's a dream of freedom and bliss. The opposite of a falling dream, which, of course, is a dream of fear and anxiety, panic. Flying is life. Falling is death. (S6 E16)

Portrayed by Jill Hennessy - 1993 to 1996.

Effects and benefits

Raymond Reddington - 218 episodes of The Blacklist from September 2013 through July 2023.

Advisor to President Diaz - She reinstates Reddington's original immunity agreement and is now in charge of overseeing the Task Force (S6)

Reddington tracks down his former mentor, who swindled him out of a massive amount of money. Vesco convinces him to help find a long-hidden pirate treasure - the De La Cruz, a Spanish shipwreck rumored to contain gold. He once tricked Raymond out of his entire life savings by convincing him to invest in a Paraguayan ranch that turned out to be a brothel and Raymond wants his money back. NOTE: Vesco’s fictional narrative mirrors aspects of his real-life history. The real Robert Lee Vesco (1935–2007) was an American financier and criminal who committed securities fraud in the 1970s, fled the United States, and lived in exile across Central America and the Caribbean, including Cuba, where he was eventually imprisoned. In the show, Vesco is rumored to have faked his death, paralleling real-life speculation about his demise.

He’s skillful at using information to manipulate people to further his agenda.

Raymond makes a bold move (S6 E10)

That look!

35 years ago, a Naval Intelligence Officer working for the U.S. government fell......fell into a relationship with a beautiful Russian woman. Unbeknownst to his superiors, that relationship, which started as guarded attraction, quickly evolved into passion, which resulted in pregnancy. They had the child. A girl, whom they both loved. What the Naval officer didn't know, but certainly should have suspected, was that the Russian woman was a KGB officer...that Katarina Rostova had been assigned to get close to Raymond Reddington and steal classified information from him. What Reddington could never have suspected was that though she was a KGB agent, Rostova's real handlers were members of a secret criminal organization, a multinational cabal working in the shadows to manipulate world governments, economic markets, trade, and international alliances. When Reddington discovered this, he confronted Rostova, who warned him that if he threatened to expose them, the Cabal would destroy his reputation, discrediting him so he could not discredit them. And that's what happened. With the help of the Cabal, Rostova framed Reddington with the very evidence you've heard in this courtroom. To prevent him from protecting his country, she made it appear as if he had betrayed it. As a result, the Cabal remained in the shadows, Rostova disappeared, and Raymond Reddington became a completely different person. A man who has done many brutal, scary, illegal things...but not a single one ever that was treasonous.

Tape Recording: They pulled me out of a meeting. This better be important. Reddington knows. He knows everything. Explain. He's discovered my identity and the existence of the Cabal. Can he be contained? He took Masha. Eliminate him. He's a decorated officer. His death would be investigated. Whatever they find, they will believe. But if we discredit him...The intelligence I stole...We leak that it came from him. No one will believe him after that. Not with the blood of 134 Americans on his hands. Agent Rostova, I told you to eliminate him. And I'm telling you there's a better way. Because you're sleeping with him. Because he has proof that the Cabal exists, proof that would be released in the event of his death. The Fulcrum. And because I love his daughter. My daughter. I want this mess cleaned up. Get rid of him or ruin him. Just get it done
by Christmas.

Reddington: Agent Ressler, do you recognize the man's voice on the audiotape? Ressler: Yes. It's Alan Fitch. The former Director of National Intelligence. Reddington: And the woman? Agent Rostova? Ressler: It was Katarina Rostova, yes. Reddington: Why did you bring me this tape? Ressler: Because the government has a legal obligation under Brady v. Maryland to provide the defendant with any exculpatory evidence that can be used in the defense. Reddington: Thank you, Agent Ressler. And may I say you are both everything I dislike about the FBI and everything I admire about it? Nothing further, Your Honor.

United States v. Raymond Reddington - "Sir, you have been a federal fugitive for nearly three decades, the FBI's Number One Most Wanted. You are the textbook definition of a flight risk and a danger to the community. Now, let me be clear...even if you were prepared to submit every last dollar in circulation on the planet, I still wouldn't grant you bail, ever."

Judge: Look at my face, Mr. Reddington. I'm not amused. Reddington: And I assure you, neither am I. But the fact remains the prosecution has intentionally failed to inform the court of a critical factor in this case. Judge: And that is? Reddington: My Immunity Agreement with the federal government, an agreement that expressly covers the charges before you and protects me from overzealous beavers like Mr. Sima and his bosses. Judge: Good Lord. You're a confidential informant.

Judge: Members of the jury, I have been on the bench 23 years, and I have never had
a defendant represent himself in a death penalty case. Mr. Reddington made the choice, and, after careful consideration, I have decided to allow him to continue down that path. As he's acting as his own counsel, he may testify in a narrative form. Mr. Reddington, I'm giving you the benefit of the doubt. Don't make me regret it. Please. Do you swear to tell the truth, the whole truth, and nothing but the truth, so help you God? Reddington: I do.

(S6 E9) Navy Intelligence and FBI Findings - Attorney Sima: Agent Ressler, did you once lead an FBI Task Force dedicated to killing or capturing Raymond Reddington? Reddington: Your Honor, I'm happy to stipulate that Agent Ressler was the FBI agent who spent the prime years of his career engaged in a futile game of whack-a-mole. Sima: As the ranking officer on that Reddington Task Force, were you familiar with an incident that occurred involving the U.S.S. Gideon in March of 1990? Ressler: I was. Yes. The U.S.S. Gideon was an Ohio-class submarine sunk by the Soviet Navy while on a secret mission in the Barents Sea. 134 men were on board. They all died. Sima: You say it was a secret mission. How did the Soviet Navy find out about it? Ressler: Because Raymond Reddington told them. Sima: Was the defendant the only one who knew about the mission? Ressler: Raymond Reddington was one of 16 people who were aware of it. 12 Naval officers and four CIA operatives on the Russia desk. Sima: If 16 people were aware of the mission, how can you be sure the defendant was the informant? Ressler: Two days before the sub was attacked, the Gideon's captain changed course to avoid weather. The change was communicated to an intelligence officer who was assigned to the mission. He was the only one of the 16 who knew the coordinates of the sub on the day in question. Sima: Who was that intelligence officer? Ressler: Raymond Reddington. Sima: So, the defendant was the only one who knew the location of the submarine. That doesn't prove he told the Russians how to find it. Why are you so certain that he did? Ressler: Because a secure KGB communique we intercepted indicated that Raymond Reddington provided the Russians with the exact coordinates where the submarine was torpedoed. Sima: Mr. Ressler, I'm showing you a document that has previously been admitted as Government Exhibit 9. Is this the communique? Ressler: It is. Sima: Please read it for the jury. Ressler: Lamprey indicates target diverted. Prior intel no longer actionable. New coordinates received... Sima: Are you familiar with the code name "Lamprey"? Ressler: Yes. Lamprey was the code name the KGB assigned to Raymond Reddington. Sima: For the defendant? Ressler: For Raymond Reddington. Sima: And is Raymond Reddington in the courtroom today?... Ressler hesitates. Judge: Agent Ressler. The man referred to in the communique, is he in this courtroom or not? Ressler: Yes, Your Honor. He is.

Reddington’s Cross Examination: Agent Ressler, my goodness, after all these years, I feel as if we actually know each other. Ressler: I know the feeling. Reddington: Have you ever heard of Katarina Rostova? Ressler: Yes, she was a KGB officer. Reddington: Would it surprise you to learn that she and I had quite a complicated history? Sex, drugs, rock 'n' roll... Ressler: Almost nothing you do surprises me. Reddington: How about that Katarina hid the fact that she was a KGB agent, stole the coordinates for the submarine U.S.S. Gideon, and passed them on to her superiors? That she, in fact, was responsible for the deaths of those brave young men?... Agent Ressler, was I a good intelligence officer? Ressler: Raymond Reddington was one of the best. Reddington: Sorry? Raymond Reddington was? Ressler: Yes. Reddington: Hated by the KGB? Ressler: Very much so. Reddington: Would they have liked to see him disgraced? Ressler: Definitely. Reddington: Enough to forge a communique? Sima: Objection! The witness cannot possibly know what the KGB would or wouldn't do... Reddington: Mr. Sima asked you if I was a traitor. You hesitated with your answer. Why? Ressler: What difference does it make? Reddington: Is it because you're uncertain or aware of mitigating circumstances that have given you a different opinion of me? About who I am today as opposed to who I once was? Ressler: I don't think you want me to answer that. Reddington: Oh, but I do. Ressler: I don't.

Attorney Sima calls Lawton Nuss to the stand to backup Ressler's testimony. 

Sima: Please state your name and occupation. Lawton B. Nuss. I'm a Retired Forensic
Accountant with the FBI. Sima: When you were with the Bureau, did you discover that the Russians paid Raymond Reddington for information leading to the sinking of the U.S.S. Gideon? Nuss: Yes, sir. Reddington: I would object, but I so enjoy a good yarn. Sima: Describe how the money was handled. Nuss: A month before the incident, a corporate account was opened in a Cypriot bank known to work with Soviet intelligence. The only person with the power to withdraw funds was the company president. Sima: And who was that? Nuss: Raymond Reddington. Sima: I'm sure many accounts were opened in the weeks prior to the tragedy of the Gideon. What makes you think the activity in this account was connected to it? Nuss: Because a front company for the KGB wired $3 million into the account a day before the incident, and another $3 million the day after it. One week later, the entire amount was withdrawn. Sima: By Reddington? Nuss: Yes, using fingerprints and a password.

Reddington’s Cross Examination: Was the withdrawal made in person? Nuss: No, it was a wire transfer. Reddington: You said the withdrawal required fingerprints and a password. Nuss: It was done remotely. Reddington: So if someone had a copy of my fingerprints and knew the password, they could have made the withdrawal, and no one at the bank, nor yourself, would have known the difference? Nuss: I, uh, suppose that's possible. Yes. Reddington: You know what else is possible? That I was framed by Katarina Rostova, which I could prove if Your Honor would grant me even the shortest...

(S6 E9) Another connection to Katarina Rostova. As Reddington tries to clear his name of treason charges, he gives the task force a blacklister who uses incriminating evidence to extort people. "I have a case. Minister D. A serial blackmailer. He takes his name from the villain in Edgar Allan Poe's The Purloined Letter. However, unlike his namesake, this man's never been identified." Why now? Today of all days? Because I'm innocent. And he can prove it. How? The explanation will be obvious once you've found him. Minister D listened to phone calls, transcribed them using a typewriter and sent blackmail letters. Task Force: Reddington told us to look for a very specific needle in this haystack. A recording taken on December 7, 1990. Cooper: Please tell me you found something. Team: We did. Just not what we were looking for. Elijah Bailey is an alias. We matched his DNA to a Jordan Loving, a retired corporal in the Army Corps of Engineers. Now, he disappeared from a hospital 4 days after he made the recording that Mr. Reddington says will clear his name. Loving was admitted with severe burns after an explosion at his house injured him and killed a man identified as Zachary Tempkin. We found this picture at Bailey's. It can't be a coincidence that Reddington is looking for a recording made on December 7th, and, on December 11th, an assassin injures Bailey and murders a man who appears to have been his lover. Maybe he used the tape to try and blackmail someone who didn't take kindly to being blackmailed. But who? And how the hell is it connected to Reddington?

Elizabeth to Minister D: Your scar. Katarina Rostova gave that to you, didn't she? She took Zachary from you. You found the tape. You blackmailed the wrong person. Minister D: I thought I could use the tapes to punish people for what they'd done. To cash in on what they'd done. To make a good living off the backs of bad people. Liz: You hurt a lot of people who deserved it. But you also hurt yourself. Minister D: No, I didn't. Katarina Rostova did. Out of all the tapes, why ask me about this one? Liz: Because Katarina Rostova took someone away from me, too. Minister D: I'm sorry. Liz: So am I. Thanks to your tape I think she just gave him back to me.

Judge: Reddington has called Assistant Director Harold Cooper to the stand. Reddington: Hello, Harold. Thank you, by the way. Cooper: For what? Reddington: Being honest. I regret I had to rely upon your integrity just to get this hearing. I wish there'd been an easier way. Attorney Sima: Objection!  Reddington: I haven't even asked anything yet. Judge: Something tells me that's the objection. Do you have a question for Director Cooper? Reddington: Just one, Your Honor, and it's this. Would you do it again? Cooper: Excuse me? Reddington: The deal we made...my cooperation in exchange for my freedom. As the man who oversaw the arrangement in all its grand and often gory detail, would you do it again? Cooper: Yes. Reddington: Why? Sorry, I had two questions. Cooper: Because it saved lives. I don't know how many since we started. Maybe thousands. Sima: Objection! Your Honor, I fail to see how this witness's subjective assessment of the agreement has any relevance to its scope as a matter of law... Reddington: Your Honor, I object to almost every thing about him, beginning with his power tie and ending with his general demeanor. Judge: Enough. Mr. Reddington, if you are going to insist on representing yourself, you will conform yourself to the rules of the court... Let the witness speak.

Cooper: We made this deal for one reason...so you could help us find those criminals we never knew existed. Reddington: And you've done that. Cooper: Violent people, evil people are dead or in prison because of you. In some cases, we recovered dangerous weapons or avoided catastrophic outbreaks... A few years ago, we learned some of those criminals were inside our own government...the Attorney General, a National Security Advisor, the very people our country depends on to maintain law and order. To be clear, none of that would have happened without Mr. Reddington. So, would I do it again? You're damn right I would.

Sima: You are aware that the defendant has been indicted on multiple counts of treason? Cooper: I am. Sima: For selling this nation's most highly classified secrets, for betraying our country? Cooper: Yes. Sima: You're aware that, for almost 30 years, he's maintained a vast criminal empire, that the charges against him as the so-called Concierge of Crime are so extensive and so heinous, they occupy a unique place in our country's history? Cooper: I'm aware of the allegations. Sima: I'm sorry. Allegations? Is it your position that the defendant is innocent? Cooper: Until proven guilty. Or is it your position that I should ignore the Constitution? Sima: My position, sir, is that some people are irredeemable, that a deal granting immunity to a man like Reddington is beneath the dignity of a country that prides itself on the rule of law. Reddington: Objection! He's arguing with the man, and, frankly, being incredibly self-righteous... Sima: Sir, is there no one you wouldn't make a deal with? If not this defendant, is anyone too offensive to be given a free pass by your standards? Reddington: Well, now he's just being insulting. Judge: I said move on, Counsel. Cooper: To be clear, nobody gave Mr. Reddington a free pass. He has to earn his freedom. There are rules he has to abide by. Sima: I see. And does he abide by them? Cooper: Yes. Sima: Really? So, to your knowledge, he hasn't committed any crimes since becoming your informant. Cooper: I won't discuss specific cases. What we do is classified and often involves matters of national security. Reddington: Okay, Your Honor... Judge: You opened the door to this. Sima: Director Cooper, does he abide by the rules or not? I'll ask you again. To your knowledge, has Raymond Reddington committed any unsanctioned crimes since becoming an informant for your task force? Cooper: I have no direct knowledge that he has. No.

United States v. Raymond Reddington

Harold Cooper to Cynthia Panabaker, White House Counsel: You can't just walk away. Panabaker: Actually, Harold, I can't do anything else. Cooper: You know the good this Task Force has done. Panabaker: Yes, I do, and the bad. We knew this was a possibility when we made his deal, which is why the government lawyers who papered it were very clear about what our position would be if it did. In the event of Reddington's arrest, we disavow. Cooper: We papered it 5 years ago. Since that time, thanks to Reddington's blacklist, this Bureau has killed or captured over 100 high-value targets and saved a tremendous number of lives in the process. Panabaker: Harold, I like you, and I admire the way you have milked this mad cow, but you knew from day one that the government would never publicly acknowledge having an immunity agreement with the #1 man on its most-wanted list. Cooper: I'm not asking you to go public. He was arrested in New York. If you inform the U.S. attorney of the Southern District... Panabaker: The publicity hound who wants to run for governor and, God forbid, president? You have any idea how long she'd sit on that intel? We'd be in turtle mode for a month of Sundays. Cooper: There must be something you can do. Panabaker: There is, and we are very good at it. Absolutely nothing. Cooper: Cynthia, I know that the Task Force has crossed lines. I know that there has been collateral damage, that Reddington is a criminal who someday must answer for what he has done, but that day is not today. Today, because of Reddington, we stopped a terrorist from bombing the United Nations. You disavow, and, tomorrow, we may not be so lucky. Panabaker: And that would be a tragedy, but there is nothing I can do about it.