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Flynn is Lucy's real father. At some point in the past, he will have a relationship with her mother, which ends on bad terms, explaining why Lucy always believed Henry was her father.

  • Jossed. Lucy is actually the child of a big wheel in Rittenhouse.

Flynn and his helpers are actually the good guys, and unbeknownst to our trio, Mason is the one trying to change history.

  • Jossed. Mason is somehow involved with Rittenhouse, but he's absolutely terrified of them.
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Flynn is purposely disrupting history as an extremely over the top way of calling out Rittenhouse

The idea being that Rittenhouse is engaged in a nefarious plot to change history for their own ends (we don't know if Rittenhouse is a person or group of people or a corporation), and Flynn is trying as many outrageous means of disrupting the time stream as possible, knowing full well that the government will step in to stop it. In doing so, he hopes to catch the attention of Rufus, Wyatt, and Lucy and get them to help wipe out Rittenhouse.

Flynn is from the future

The notebook makes it pretty clear that either he's from the future, or he's in contact with people who are. It's probably a Bad Future, and given that he wants to destroy Rittenhouse (whatever it or they might be), they're probably involved in making it that way, whether directly or indirectly. Either way, they did something bad enough for Flynn to think that the only way to prevent it is to eliminate Rittenhouse altogether, no matter what other damage his actions might cause.
  • Jossed, as to the central premise, but elements of this are confirmed. Rittenhouse assassinated his family just because he stumbled on covert monetary transfers to Mason's time travel company, and as a consequence Flynn has decided to wipe out Rittenhouse completely.
  • In "The Red Scare" Flynn comments to Lucy that she "ages very well", implying that Flynn either is from, or has visited, the future.
    • Or that he's been visited by someone from the Future. While the limitation of visiting a time you already exist in is a problem, there's no reason why Lucy couldn't visit Flynn during a time when Young-Lucy is in the past, taking advantage of San Dimas Time.

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Flynn is Lucy's Son

Lucy, Wyatt, and Rufus continue to change the timeline, until it becomes unrecognizable to them or America descends into a dystopian nightmare or somesuch. Lucy begins to keep a journal of all the events that she remembers happening, but that are now different because of time-travel meddling. The trio regret their actions, but as they cannot travel back to a point they previously changed they are unable to un-do the damage they've caused. Lucy eventually has a son, names him Flynn, gives him the journal, and tells him to go back in time and stop her from upsetting the timeline. He accepts, with the full realization that if he succeeds in his mission he can never return to his own future, as Lucy would never have become his mother.
  • Jossed, unless he's lying, as his stated motivation is to get his family back.
  • Also Jossed by the fact that we're eventually introduced to his mother, Maria Thompkins.

The Space Race unfolds entirely differently after Apollo 11

Every aspect of the Apollo Program is heavily scrutinized after the communication failure that almost doomed Apollo 11. As a consequence, the defect in the oxygen tank stirrer that caused the Apollo 13 disaster is caught and that mission is flown without incident. Apollo 18-20 receive funding as well. On the other hand, the fake Moon landing conspiracy theories are even more virulent in the resulting timeline, with theorists claiming NASA had to generate footage on the fly after Apollo 11 crashed.

Lucy will become Flynn's wife

That would explain a lot about the strange fixation between them, his seeming unwillingness to kill her, and the reason why her future journal is in his possession.
  • Now that Jessica is back, the relationship between Lucy and Wyatt appears to be over. Flynn is on the same side now, and increasingly appearing to have been Right All Along. As of the ending of "The Kennedy Curse", neither is making an overture to the other, but there appears to be a moment of bonding. It could happen.
  • But then Jessica turns out to be Rittenhouse, eventually driving Wyatt to an Anguished Declaration of Love to Lucy.
    • Ultimate Jossed He sacrifice himself to get Rufus back although according to the journal he have an relationship with Lucy in an alternative timeline. Regardless Lucy names one of her daughters Flynn after him.
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Future Lucy wrote the journal, and sent it to Flynn as part of a plan to stop Flynn and get her sister back.

Her plans include her and the team thwarting Flynn a lot of the time—and she leaves that out of the journal so that Flynn won't skip any of the crucial parts of the plan.

The Rittenhouse family is special because they retain memories of timelines after they've been changed.

In a conversation with Lucy, her father knew things that have since been undone by time travel. Similarly, Lucy instinctively knew what to check when Wyatt came back from a rogue trip to The '80s.
  • Actually, her father probably just knows about Lucy's sister and the fact she didn't used to be engaged due to spying on the team's conversations.

Jiya has acquired the ability to see multiple timelines

At one point she sees what could be a flashback to the 1930s, but it could be that of an alternate timeline.
  • Jiya also sees the Golden Gate Bridge in ruins which could either be a vision of the future or of an alternate timeline.
    • The Golden Gate flashback actually shows the bridge under construction, with cranes operating and stacks of uninstalled components visible on the unfinished spans, so it’s a look at the past. However, it’s gone so quickly that it’s practically a Freeze-Frame Bonus, so it’s very easy to think it shows a ruined Golden Gate unless you’re able to pause at just the right moment.
  • Played with. She is confirmed to be able to see possible futures. Whether or not they always come back is debatable. Her vision of Rufus's death differs in details, but the outcome was still the same.

Watergate was orchestrated by Rittenhouse

Nixon was terrified of Rittenhouse, but also the one person at that point in history who could have possibly posed a serious threat to them. It makes sense that Rittenhouse would have infiltrated the press in order to steer suspicion away from their own activities; Woodward and Bernstein were likely Rittenhouse members to whom Mark Felt was unwittingly giving information. Given that Rittenhouse has already assassinated JFK, they aren't above taking down a president, but a second assassination would have put their plans at risk. Either politicians and law enforcement not affiliated with Rittenhouse would launch a massive investigation into the deaths of two presidents from opposite parties in the space of a decade, and/or the Soviets would perceive instability in the US government and decide it's a good time to launch World War III. So Rittenhouse sets out to discredit Nixon instead—and Nixon, being Nixon, made it very easy to do.

Lucy's fiancee was also Rittenhouse

Members are born into the organization, and comments made by Lucy's mother indicate that there is a social elite within Rittenhouse based on how long one's family has been involved with them. It makes sense that Lucy's fiancee is also a scion of an elite Rittenhouse family and the marriage is meant either to fulfill an organizational goal or to cement an internal political alliance. It's very likely that this is an Arranged Marriage.

Flynn tried to destroy Rittenhouse even earlier in history

Flynn tried to invoke the Grandfather Paradox on Rittenhouse by trying to assassinate one or both of his parents, but failed. The most likely outcome is that David Rittenhouse's historical mother was killed, but his father survived and remarried to a woman who would become alt!David's mother. This would explain why David Rittenhouse had one son instead of two daughters as in our history, and the Historical Villain Upgrade: his genetic makeup and personality had changed as a result of Flynn's meddling.

Connor Mason is the son of 'the Doc'

In "The Watergate Tapes", the trio help 'the Doc' escape to Hong Kong, where her family is hiding. She mentions that her child was recently born. Given that 'the Doc' is a young African-American woman who was born into a 'Rittenhouse family', it just might be possible that her child eventually grows up to become Connor Mason. The child would have been born in 1971, and that seems to fit with Connor Mason's age (he appears to be someone in his forties). This might be the reason why Rittenhouse contacts Connor and makes him such a crucial part of their plans - unknown to him, he is a Rittenhouse member by inheritance.

Jessica died in the new timeline to avoid a Grandfather Paradox

This of course assumes that time (or fate) has some kind of 'self-correcting mechanism' at work. Maybe it's impossible (or near-impossible) to willingly travel back in time and intentionally change the past in a way that prevents you from having any motivation to travel back and change the past in the first place (aka the classic Grandfather Paradox). Wyatt can't save Jessica, because if he did so, he would have no reason to hijack the time machine and jump back to 1983 in the first place. Now, Ripple Effect-Proof Memory takes care of the minor details - for instance, if in the new timeline, Wyatt had some other clues about the killer and he and Rufus steal the machine, the moment they leave the present, they land back in 1983 with memories of the 'original timeline' and original killer intact. But it's essentially that Wyatt actually has a reason to get into the machine in the first place.Now how does this work in the context of all of Flynn's trips? It's worth noting that none of Flynn's missions actually succeeded the way he wanted to, because of the team. The team's actions are probably a consequence of this 'self-correcting mechanism'. Flynn goes back to change the past, potentially causing a Grandfather Paradox. The team goes back and stops him. This results in a Close-Enough Timeline where the alternate versions of Flynn and the team both have a reason to go back in time in the first place, following which their original memories are restored. So far, in the entire series, there hasn't been a single case where someone has traveled back with the specific purpose of altering history and succeeded entirely.
  • Note that someone else trying to save Jessica can work, and eventually does.

The timeline Flynn is creating is the way history was meant to go.

He's just trying to Set Right What Once Went Wrong.

The Kennedy family timeline is changed.

While JFK wasn't able to avert his own assassination to any great extent, he is the only person from the past who's seen detailed information about the future. He can modify his own behavior in the time he has as a result. His own limited time in office may be much more ambitious, and he could have warned his siblings and his son in such a manner as to not betray his knowledge of the future to them. Joe Jr. isn't killed in World War IInote  RFK avoids assassination. Ted attempts to save Mary Joe Kopechne and/or calls for help immediately after the accident instead. John F. Kennedy Jr. avoids flying at night until he's more experienced as a pilot.note  JFK may have also avoided his skirt-chasing tendencies so that his legacy wouldn't be tainted by accusations of infidelity.

The Salem Witch Revolt becomes a landmark event in the women's rights movement.

The women sentenced to hang at Salem who (according to the changed history) fought back and escaped become the earliest heroes in the women's rights movement, and are held up as examples by the women's suffrage movement and the mid-20th century feminist movement. Emboldened by such ferociously strong role models, women's rights advocates may be able to push for equality sooner and more successfully than in our timeline. Given the experience of his mother, Benjamin Franklin may become one of the first prominent male advocates for women's rights (just as he was one of the first prominent abolition advocates in our timeline).

Jessica is Lucy's paternal half-sister and was always a ranking member of Rittenhouse.

Which is the real reason why her photo was on that Rittenhouse hard-drive Mason was working on.
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