Summary

• "I can only lead you to the truth." - Reddington's prophetic quote emphasizes his role as a guide throughout the series.
• "A man who's willing to burn the world down to protect the one person they care about, that's a man I understand." - Reddington values loyalty and will go to great lengths to protect his loved ones.
• "Once you cross over, there are things in the darkness that can keep your heart from feeling the light again." - Reddington warns Ressler about the consequences of crossing moral boundaries.

James Spader's character in NBC's hit show The Blacklist is a man of many words, and the best Raymond Reddington quotes show why he's become the face of the show. Much of this character's charm is due to his sharp tongue, quick wit, and control of the English language. The lovable criminal portrayed by James Spader is known for his long-winded monologues, tall tales, and clever one-liners. His dialogue sometimes serves as humor, sometimes as wisdom, and other times the audience is just as lost as the characters Reddington is talking to. However, among all the nonsense lies some truly remarkable, inspirational, and unforgettable Raymond Reddington quotes.

The best Raymond Reddington quotes are a key reason The Blacklist was such a hit for NBC, with Spader's performance earning him a Golden Globe nomination in 2014. The Blacklist wrapped up in 2023, and Red finished the story in his own unique way. While he no longer had Liz to trade barbs with, fans continued to see James Spader deliver many more memorable and incredibly quotable Raymond Reddington lines during his final season on the show.

25 "Lies By Omission Are Still Lies, Harold. Some Would Argue They're The Worst Kind."

Raymond Knows The Power Of A Partial Truth

Raymond Reddington knows a lot about lying, since he has an incredibly complex relationship with the truth. To say he's known to bend and twist facts to suit his plans is an understatement. However, this Raymond Reddington quote from a conversation with Harold Cooper shows two things — that he's not unaware of the moral implications of lying, and that he knows that withholding aspects of the truth still counts as deceit.

Raymond is a master of lying by omission. There are many times in The Blacklist that he manages to manipulate those around him by only partially revealing the truth, leaving out key details to skew and shape the reactions of those he's speaking to. As is evidenced by this Raymond Reddington quote, the mysterious character is fully aware that often deceit by omission is more effective than outright falsehoods — and both methods are just as ethically questionable.

24 "People Say Money Can't Buy Happiness, But It Can Buy You A Yacht Big Enough To Sail Right Up To It."

The Raymond Reddington Take On A Common Idiom

There are many moments in The Blacklist that are memorable due to Raymond Reddington putting his own spin on common idioms, though few are as poignant as his take on the saying "money can't buy happiness". Reddington is shown time and time again to have an incredibly uncanny understanding of the way the world works, and this extends to his views on money.

As a criminal mastermind, it's a given that money is a key motivation for Raymond Reddington, as it's unlikely he became the FBI's most wanted simply because he enjoys playing mind-games with law enforcement (even though he's incredibly good at it). This quote, however, shows that it's perhaps not the money itself that's important to Raymond, but what he can achieve with it. Despite his incredibly complex character, Raymond's end-goal is the same as almost everyone's — a peaceful, happy life. Where he differs from others is, clearly, his definition of happiness, and the lengths he's prepared to go to get the money that will enable it.

23 "There's Nothing That Can't Be Accomplished With A Little Ingenuity And A Lot Of Explosives."

A Funny Quote That Reveals A Lot About Raymond Reddington's Philosophy

This is a Raymond Reddington quote that's incredibly funny on the surface, but also reveals a lot about his approach both to life and to his criminal dealings. Raymond Reddington is a mastermind when it comes to social manipulation. There are dozens of moments in The Blacklist that show this, and it's often the cast that Raymond has been behind the scenes pulling the strings to ensure his various plans come to fruition without a hitch. However, there are also times when he simply resorts to murder.

While he always seems to prefer nuanced ways to overcome obstacles in his path, there are other times when he simply opts for violence and killing to remove those in his way.

This mixed approach is summed up incredibly well by this quote from The Blacklist. "A lot of explosives" is meant literally, of course, but it can also be seen as a metaphor for the times that Raymond resorts to blunter solutions to problems. While he always seems to prefer nuanced ways to overcome obstacles in his path, there are other times when he simply opts for violence and killing to remove those in his way. With this quote, Raymond demonstrates that even the most astute criminal mastermind sometimes needs to take direct action.

22 "There's No Such Thing As Luck. Just Well-Placed Opportunities."

Raymond Reddington Has No Time To Think Himself Lucky

There are many characters in fiction who can be said to make their own luck, and Raymond Reddington could definitely fall into this category — as much as he himself would heavily dispute this, as this The Blacklist quote shows. There are many moments in The Blacklist when Raymond Reddington's carefully-laid plans and schemes can be said to have worked because of various lucky breaks. Raymond, however, doesn't believe in luck. All that he sees in these 'lucky' moments are sudden opportunities that he can use to his advantage.

While viewers may dispute whether luck has helped Raymond Reddington in his criminal career, the character himself would clearly attribute none of his success to it. Given how deftly he seems to be able to manipulate the situations and circumstances he finds himself in, it's clear that his approach when it comes to how he views luck is working for him. What can't be disputed is that, whether they're considered lucky breaks or well-placed opportunities, Raymond is a master at using them to advance his goals.

21 "The Past Is A Ghost That Never Truly Leaves Us."

Of all the memorable Raymond Reddington quotes, this one is perhaps the most poignant given his mysterious backstory and connection to Elizabeth Keen. While very little is ever confirmed about the origins of Raymond Reddington, it's clear he didn't become a borderline-sociopathic criminal mastermind by choice. It's heavily implied that he became the character fans of The Blacklist love so much due to experiencing some kind of deep trauma.

His connection to Liz Keen, and the fact he kept such close tabs on her throughout her life, is also a key reason this Raymond Reddington quote particularly stands out.

His connection to Liz Keen, and the fact he kept such close tabs on her throughout her life, is also a key reason this Raymond Reddington quote particularly stands out. It shows that even the great Raymond Reddington isn't immune to the effects of the past, and that — despite the fact he does his best to appear emotionally aloof and distant — he has a deep connection to events and people earlier in his life.

20 "I Can Only Lead You To The Truth."

Raymond Reddington On His Only Path

In the first season of The Blacklist, Raymond Reddington was already leaving breadcrumbs to his motives, and for him, it was always about getting things done. However, he also knew that he could only do so much. In this case, there was evidence that Tom Keen was responsible for a murder, but there was also some chance that Red was setting up the man. However, it made Liz question whether she could trust Tom. Red then said, "I can only lead you to the truth. I can’t make you believe it."

This was an incredibly prophetic Raymond Reddington quote. Of course, Red was right about the truth being one Liz struggled to come to with. Tom turns out to be a villain the entire time, which leads to Liz shooting him. This was just one of many times that Red helped Liz and the FBI without being completely open with his knowledge, setting up a game he played throughout every single one of The Blacklist's 10 seasons.

19 "That's A Man I Understand."

Raymond Reddington On What Impresses Him The Most

Raymond 'Red' Reddington has a lot of quotes that he loves to say he lives by. However, when it comes to his ideas of what it means to be a man and to stand up for what he believes, he always lives by this one specific quote. In full, it has him saying, "A man who's willing to burn the world down to protect the one person they care about, that's a man I understand." Red has always been someone who will do anything in his power to protect those he loves, and this slams that point home.

This Raymond Reddington quote came as Red was talking to Liz about why Barnes would do anything in his power, no matter how devastating, to protect the life of his child. He also made it clear he would do anything to protect Liz and keep her alive, even if he couldn't follow through on that promise in the end.

18 "Have I Threatened You Before?"

Raymond Reddington Makes His Presence Known

Red Reddington has prided himself on delivering one-liners that ensure that the person he is speaking to knows exactly who he is and what he is capable of. He also makes sure that anyone he is talking to knows that he is not someone to be messed around with. What was best about this quote was that it wasn't a threat or an intimidation tactic. One of the best Raymond Reddington quotes, it was here just a source of confusion for the man.

What is funny is that this isn't a quote only used on The Blacklist. This was also a quote that Captain Jack Sparrow used in the first Pirates of the Caribbean movie when he met Will Turner. It worked in that situation as well, and, for men like Raymond Reddington and Jack Sparrow, all the confrontational encounters merge into one after a while.

17 "I Consider Jealousy To Be A Base Emotion."

Raymond Reddington On Ignoring One Rule

Reddington has never found it easy in The Blacklist to give his trust to anyone. However, with Elizabeth, that was all different. As their relationship strengthened, Elizabeth began to feel jealousy at certain things in Red's life. When Raymond Reddington was searching for Zoe, and Elizabeth believed she might be his daughter, she showed jealousy at that entire situation. That caused Reddington to just tell her, "As a rule, I consider jealousy to be a base emotion, but in this case, it’s quite endearing." It was a nice way to let her know it was okay.

It subtly shows the more human side of his enigmatic character.

Of course, Zoe wasn't Red's daughter but was the daughter of Milos Kirchoff, whom he wanted to help the two reunite. Raymond Reddington was always one step ahead, but even in that case, he knew how Elizabeth felt about him, and he was willing to drop some pretenses to let her know he was there for her as well. It subtly shows the more human side of his enigmatic character.

16 "There Are Things In The Darkness"

Raymond Reddington On Going Too Far

Raymond Reddington knows what it is like to do bad things. He also knows there is a need to warn other people about when they are about to cross over that line where there is no coming back. This is made apparent in a Raymond Reddington quote taken from while he was talking to Agent Donald Ressler. Reddington tells Ressler, "Once you cross over, there are things in the darkness that can keep your heart from feeling the light again." When Ressler says all he feels is hate, Reddington says that it is "Good, You're gonna need it."

This came in the wake of FBI Agent Sam Raimo, who disemboweled himself to save his own family from a Yauka Boss he had previously arrested while hunting down Red. While seeking out Tanida, the Yakuza boss kills Ressler's former fiancé in front of him. When Ressler learns it was his old friend Jonica who caused Tanida to come after everyone, he finally steps down from killing him himself and allows the man to commit seppuku, the same fate that Raimo suffered.