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Mr. Fitch dropped few clues for us in the mid-season finale about the missing years of Red's life. We learned Fitch last saw Red right at the beginning of Red's life of crime. We also know Red set up a safety net for himself, ensuring the release of certain secrets, if he turned up dead. Fitch seems to know Red well, from before his criminal days. They made some kind of an arrangement where they don't interfere with Red, so long as he keeps their secrets.

As I see it there are three options:

1) Red was abducted by the Adversary and spent the four years in captivity, before being rescued by Fitch's shady government organization.

2) Red was abducted by Fitch's shady government organization and spent four years in their custody before they released him/he escaped.

3) Red spent the first four years trying to track the Adversary on his own, but ultimately realized the plan wasn't working and that he'd need to build a powerful organization of his own to have a chance of succeeding. He arranged a meeting with Fitch to blackmail him into giving him the intel he needed to start his business.

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Interesting theories here. I believe that while in the Navy Red was ordered to partake in a mission that he felt was morally wrong and spoke up about it. He then was abducted on his way home for Christmas in 1990, help prisoner while Mr. Fitch and his people released documents seeming like they came from Red to tarnish his name. Then either released him telling him that nobody would believe him if he told what he knew since he was now a wanted man for treason, and figured they would let the FBI take him down and deal with him.

Then Red, being as smart as he is, compiled proof of this mission and set it up to be released upon his death, then confronted Mr. Fitch to let him know this information and then was forced to lead a life of crime in order to survive. Hence his response to Ressler when he asked "How could you do it Red, give up the flag and betray your country". Red responded "We become what we are" or something to that effect. Which leads me to believe he didn't chose a criminal life he was forced into it. And now he wants to redeem himself before he dies or gets too old to continue doing what he is doing.
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I love the part of your theory that Fitch's group abducted Red and that they were the ones that that released the documents to trash his name. I think Red must have already had the safety measure in place before he was abducted, otherwise I think they would have killed him in those four years. I think they thought they would be able to torture the information out of him, but couldn't and they were worried about Red being declared legally dead before they could disarm Red's safety measure. Linking Red to treasonous activity would be an excellent way to remove him as a threat. I'm not sure where the Adversary, Liz, the attack on Red's family, and the girl in the photo fits in, but I definitely think this could be a piece of the story.

I also agree being a criminal wasn't something that Red ever wanted, it was a choice forced upon him by circumstances. Red says "You can't judge a book by isn't cover, but you can by its first few chapter, and certainly by its last." At the being of Red's story is a hero and a family man, the middle chapters, the ones we are supposed to ignore are the criminal years, and the last chapter is now, his years helping the FBI. This tells us how Red views who he really is.
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I think Red started out being on a deep cover assignment for Naval Intelligence. But over time, the cover story became real. All that power and money in his grasp; why give it up?

But Fitchs' group and the Adversary became too dangerous for him to deal with, or avoid. And vice versa.

Long term, the only way Red is going to survive is to take out the two groups. And the FBI is able to provide him with cannon fodder. Why sacrifice your own, loyal, CAPABLE minions when someone else is willing to do so for you?
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I don't think Red's motivations will end up being that selfish. The writers have spoken about Red's desire for redemption through Liz. I think his plan is motivated by something much more powerful than greed. His is not above using the FBI for his goal, but Red's behavior in Anslo Garrick shows us that self-preservation is not his number 1 priority.
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Who's Finch?
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Alan Alda's character. NBC's website calls him "Mr. Fitch" although originally the man was named Crowley.
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Hmmm, not sure about the timeline here - Fitch (or Crowley, this name-stuff is confusing) said he hadn't seen Red in 20 years, right? Since he went off grid in 1990, that would mean they could have been in touch for those three years before Red shook off the shady "bigwigs" and set out with his carefully prepared timebombs of sensitive secrets to ensure his safety and freedom.

So Red may have been roped in to go into deeeeeeep cover in 1990, perhaps starting out his criminal career as an unwilling, but loyal officer, and after three years he's become disillusioned, cynical, lost his family, etc, and says "Sayonara, douchebags!" and sets out on his own - or perhaps he's realized the people he's working for are the REAL bad guys, and sets out on a decades long quest to take THEM down?

Wondering about Liz too, by the way - she has a degree in psychology, if I'm remembering the pilot correctly, and she was HEAD of the NY Mobile Psych Emergency unit or some such, suggesting she didn't get the position when she was fresh out of college. Add BSU-training at Quantico - basic agent training is 20 weeks, but the BSU seems to do its training on a more individual level, when resources are available/needed, so there's no telling how long that took, and I find it hard to believe that she was 4 years old in 1990, which would make her 27 today...
Judging by the way she's presented in the show, she COULD be 27, but based on her CV, I'd add a few years to that - unless they just want us to realize how truly gifted she is.

Anyway, in my mind she's too old to be a four-year-old daughter left behind in 1990.

So, anyway - I see "spent three years or so in more or less voluntary undercover work" as a viable option here.
The question is if he was hunting the Adversary then, and still is - or if Fitch and his fellows are his main enemy now? Somehow, I doubt it - I don't doubt that he would gladly take them down, but I don't think they're his focus.
Unless they target Liz, of course.
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I think Liz would have to be 28, she was adopted at 4, and Red was missing 4 years and and active criminal for 20. According to NBC Liz became "received board certification after three years with the FBI". For her to take that exam she would need to have finished 5-7 years of education after getting her BA. She would have been between 26 and 28. She was with the FBI for one year after that, according to the pilot, where she says she has been with them for four years. Assuming she didn't take any time off anywhere in there, she is between 27 and 29 years old. This naturally tells us nothing. Maybe we will get lucky and someone will throw Liz a birthday party...

Good thought on the deep cover work, although for him to have accepted that assignment, something would have had to happened to his family first, which means he must have already done something that made someone very bad (probably the Adversary) very mad...whatever that something is I feel is somehow tied to Liz.

I think, you're right, the Adversary is Red's focus, but that he is not a fan of Fitch's crew either. Two questions remain: When did Red set up his insurance policy? and What is Fitch's group worried about being exposed? My theory: Fitch's group recruited Red out of Naval intelligence and tasked him with infiltrating the Adversary's organization. Sam was Red's handler/partner in the operation. They gather enough intel on the Adversary to put him away, but instead they choose to leverage it to get force the Adversary to work for them.

Unfortunately for Red he has personally pissed the Adversary, by A) marrying his daughter (Liz's mother), B) Running away with his pregnant wife/mistress (Liz's mother) or C) Taking his daughter (Liz) and giving her to Sam to raise. Eventually the Adversary turns the tables and comes for Red and his family.
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Hmmm... What if nothing had happened to Red's family when he went undercover, but he went anyway (which is where the reluctant, but loyal bit comes in), perhaps only expecting to be gone for a short time. He asks his good friend Sam to look after his family while he's gone, everything goes sideways with the fire and what not, and Sam adopts Lizzie.

Or, given that it's becoming increasingly believable that Lizzie is NOT Red's daughter:
What if she was his step-daughter, while he was undercover? He hooks up with deadbeat single mom-with-kid, grows fond of her, especially as he can't be with his REAL family, and then stuff goes sideways - that way, Red could a) be the "career criminal" father they refer to in the pilot, b) not be genetically linked to Lizzie, c) NOT be her father, and d) qualify for the statement "It's complicated" (or words to that effect) which he uses at one point.
When everything comes crashing down, i.e. he's captured by The Adversary, or pulled out of the assignment by Fitch and his group, or something completely different, his handler/old friend/only contact with his old life - Sam - steps in.
Or maybe this is when his real family gets attacked and everything comes crashing down, and that's what gets him to stay under; he has nothing left to go back to?
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I have trouble believing the 1990 deep cover theory if nothing had already happened to his family. The way they found his car on the side of the road with the Christmas presents in the truck invites too much speculation and attention. Someone would have reported him missing. He may very well have met Lizzie while he was under cover, but I think it would have to have been prior to 1990. One thing is for certain though, something happened December 1990, because that is the date that is written on the stewmaker's photo. The girl in the photo is 12, which I think is too old to be Red's daughter. I would speculate her death must be connected to the tragedy at Red's house OR a mission against the Adversary that went wrong and Red feels responsible for her death.

The thing I struggle to make sense of, if Red is really not Liz's father, are these words to Sam, "You will always be her father, Sam. I can only hope to love her and protect her as you have." That sounds like Red is reassuring Sam he would never try to take his place as Liz's father. Why would that fear exist in Sam's mind at all, unless there was a some reason Red might have a claim to that position? What if Red did raise Lizzie, but she was not his biological child.

Red could have been undercover on an assignment met Liz's mother, who was the Adversary's wife/mistress, fell in love with her help her and her child escape the adversary, married her and raised Liz until the adversary caught up with them.

Another possibility is that he was pursuing the adversary in order to assassinate him, the mission went sideways. Liz's mother died, the adversary escaped, and baby Liz was left behind. Raymond decides to take the child and raise her as his own.
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I've always kind of thought he learned something while on mission for whatever government group (the Navy, I think) that he and Sam both worked for that he knew would get him killed, so he went into hiding. And he needed assistance while in hiding but that was when he got access to government secrets and whatnot (it would stand to reason that he continued to hold a few of those secrets and one of them is Crowley's group's) and decided he'd be as corrupt as everyone else.

I have had another thought that the 1990 disappearance is when if you go with that Red is Liz's father when Sam took over. What if Red had provided Sam with a new and totally scrubbed identity together with his daughter and heck maybe his daughter's name was Eliza, or Alyssa or something where Lizzie is still a possible nickname and Sam just registered her in nursery school as Elizabeth. I mean, it kind of clears up Liz's background, Sam's story could just be that an old girlfriend dropped her off one day and promised she'd be right back, so Sam took her in.
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