[WARNING: Post contains spoilers for The Final Dossier.]

From the very beginning of The Return, I was intrigued by the character of Ray Monroe, so I was excited when I heard there would be a Ray chapter in The Final Dossier. I went into it thinking I would get some answers about the man who (almost) got the drop on Mr. C. but after reading the Ray chapter, I was left wanting more. We know Ray was a paid FBI informant, but who was he before that? Where did he come from? And, perhaps more importantly, how much did he know about the extra-dimensional aspect of the work he was doing?

We are led to believe early on that Ray is just another one of Mr. C’s employees—an average criminal who somehow got involved in DoppelCoop’s extensive network of bad guys. We don’t know what else Ray may have done for Mr. C, but in Part 2 we learn that Ray’s current (and most important) task is to acquire the coordinates from William Hastings’s secretary, Betty. Mr. C can deny it all he wants, but he NEEDS the coordinates, and he’s tasked Ray Monroe with getting them.

It’s clear from the start that Mr. C doesn’t trust Ray. He’s a bit too cocky for Mr. C’s liking and he asks too many questions. Mr. C is also very suspicious of the fact that Betty will only deal with Ray. It’s not long before we get confirmation that Ray and Darya are planning to double-cross Mr. C, which comes as no surprise to the boss man. He had already killed Jack and was all set up to record Darya’s incriminating phone call; he just didn’t have all the pieces of the puzzle. He needed to know who was behind the plot to kill him.

According to Ray’s phone call to Darya, made from a burner inside federal prison, the person who put the hit out on Mr. C is the long-lost Phillip Jeffries. Even though Ray had just referenced “Jeffries” on the phone, Darya tells Mr. C she doesn’t know who hired them—that only Ray knows and didn’t tell her. Perhaps she’s just playing dumb in a desperate attempt to save herself, but the fact that Ray mentioned Jeffries on the call is pretty solid evidence that she did know, and this isn’t lost on Mr. C. This begs the question of exactly how much Darya knew about Ray’s involvement with Jeffries. The fact that she was engaged in a sexual relationship with Mr. C is pretty solid evidence that Darya wasn’t an informant herself, but she definitely knew more than she let on.

Darya’s reaction to the symbol on the playing card has always fascinated me. She knows Mr. C is about to kill her, but when he shows her the playing card she seems even more scared of it than she is of him. If Darya was truly in the dark about everything, why would a random symbol give her such a visceral reaction? I believe that Darya had some knowledge of the Lodge-related aspect of the whole thing and this information would have had to come from Ray.

Darya’s story is cut short pretty quickly (and The Final Dossier doesn’t mention her) so we will likely never know the extent of her knowledge. But as The Return progresses we learn more about Ray (although, in true Twin Peaks fashion, this information presents more questions than it does answers). The central mystery, at least to me, is not whether Ray was working with the actual Jeffries—I believe he was, and Jeffries himself seems to confirm that when Mr. C goes to see him at The Dutchman’s in Part 15. When Mr. C asks Jeffries, “Why did you send Ray to kill me?” Jeffries responds, “What? I called Ray.” This doesn’t answer Mr. C’s question per se, but it does confirm that Jeffries knows who Ray is.

The real mystery here isn’t if Jeffries was working with Ray but how they were working together. With Jeffries only really existing in some sort of ethereal state at The Dutchman’s—a place itself not of this world—how did he recruit and stay in contact with Ray? Ray claims that he only ever spoke to Jeffries on the phone. While I’m willing to concede that Ethereal Teapot Jeffries can make phone calls, I keep going back to Ray’s final words about The Dutchman’s: “It’s not a real place.” If he’d only even spoken to Jeffries on the phone, how would he have any conception of the true nature of The Dutchman’s?

Let’s examine what The Final Dossier tells us about Ray Monroe:

– Ray was a deep-cover informant recruited by “someone involved in [the Blue Rose] task force” to work on the “missing Cooper” case.

– Ray penetrated Mr. C’s inner circle and worked with him in the “months or weeks” prior to Mr. C’s surfacing in Buckhorn.

– Tammy believes that Ray first came in contact with Mr. C in Las Vegas. In her preparation of the dossier, she came across a “vague reference” indicating that two years earlier, Ray began the operation in Vegas where Mr. C had established part of his organization with Duncan Todd as the principal operative.

– Tammy came across a “partially garbled phone message” to an agency intermediary, in which Ray claimed that he was reporting directly to a Blue Rose Task Force member but did not identify this person.

– At some point before his death in Western Montana, Ray made a call from a burner phone later found at the location of his body. Based on the data retrieved from the phone, Tammy concludes that Ray believed he was working for and had initially been recruited by Phillip Jeffries.

– They found a relatively new matchbook from The Dutchman’s on Ray’s body at The Farm, but the real-world Dutchman’s motel was demolished in the late 1960s.

The presence of the matchbook from The Dutchman’s opens up a very interesting possibility—and one that I’ve been toying with since The Return. I think it’s very possible that Ray Monroe has been to The Dutchman’s to “see” Jeffries. I also believe that the “intermediary” that Ray contacted was the “Impostor Jeffries” that Mr. C spoke to in Part 2. In our Black Lodge/White Lodge series article, “Judging Jeffries,” I took the position that Impostor Jeffries was MIKE, and I stand by that theory. I would add at this point that I think Jeffries and MIKE were working together to get DoppelCoop back into the Lodge. We know that Ray ended up with the Owl Ring and that the last person seen with the ring was MIKE, who got it after the Dougie tulpa disintegrated. Ray tells Mr. C that he got the ring from some random prison guard, but since Ray is constantly lying to Mr. C and knew he was about to die, I don’t think we can take this as gospel truth.

We know from Part 17 that MIKE is able to physically enter The Dutchman’s, and I believe MIKE brought the ring to Jeffries after he got it back from Dougie. I would argue that, at some point before his “arrest,” Ray physically visited The Dutchman’s, which is where he acquired the ring (and the matchbook) along with instructions from Jeffries on how to use it once he killed Mr. C.

There are several instances that point to the fact that Ray knew more about the Lodge aspect of things than initially suspected. First, when he calls Jeffries after he witnesses the Woodsmen with Mr. C in Part 8, Ray says, “I saw something in Cooper. It may be the key to what this is all about.” He also says that Mr. C got “some kind of help” (which, for my money, is the funniest line in the entire Return) but he doesn’t seem as freaked out by the whole situation as one might expect. Someone with no Lodge experience or knowledge, seeing a bunch of semi-transparent men emerging from nowhere and performing some sort of ritual extraction of a demon egg from a man’s body, would probably have some serious questions for his handler. After the initial shock and terror of seeing the Woodsmen reveal BOB to him, Ray seems (relatively) calm as he leaves a message for Jeffries. He seems more confused than anything else, as if he is to some extent aware that entities like this exist but he’s not quite sure how they operate.

Another thing that sticks out to me is the scene right before Mr. C kills Ray, when Ray tells him, “I know who you are.” To be fair, a lot of what Ray tells Mr. C in this scene is bullshit. He lies about the coordinates—he got them from Jeffries, not Betty. There’s no evidence to suggest that Betty would have even had access to the coordinates, and even if she did, the Hastings/Ruth coordinates are not the same as the trap coordinates Ray gives to Mr. C. He also lies about Jeffries not mentioning Major Briggs, which is later confirmed by Gordon in Part 17 when he tells Tammy and Albert that Ray “sent a cryptic message indicating that the Cooper we met at the prison is looking for coordinates—coordinates from a certain Major Briggs.” But despite the fact that Ray is lying through his teeth about a lot of things, the line “I know who you are” rings true to me. He’s a Blue Rose informant, after all, and it doesn’t get any bluer than Mr. C.

At this point, Ray knows he’s going to die. He knew it pretty much the second Mr. C started arm wrestling Renzo. At this point, an aside: can we please as a fandom just take a moment to appreciate George Griffith’s facial expressions during the arm wrestling scene?

Ok, moving on.

I think when Mr. C tells Ray to put on the ring, he knows exactly where that ring is going to send him. Ray’s body stays in Montana and his soul (or whatever you want to call it) ends up in the Lodge. Perhaps this was part of Jeffries’s plan all along, or perhaps it was Mr. C’s way of giving that f^cker Ray his just deserts. Either way, Mr. C comes out on top and lives to fight another day and Ray gets a one-way ticket to Lodge-ville.

Of all the characters in The Return, I would not have guessed that Ray Monroe would end up as a Lodge dweller, but I’m intrigued by what his Lodge life would be like. Is he doomed to lie on the black-and-white floor, bleeding from the head for all eternity? Is he going to wake up and start hanging out with Leland? Will he continue to do MIKE and Jeffries’s bidding from beyond the grave? We’ll likely never know, but as frustrating as the not knowing is, there’s something to be said for keeping the mystery alive.