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This is a "Wild Mass Guess" entry, where we pull out all the sanity stops on theorizing. The regular entry on this topic is elsewhere. Please see this programme note.
Jessie
Luke's birth mother was an unwed teenager.
That's why Christina Ross was afraid to tell him the truth and thought he was too young to understand. That's also why the audience doesn't get to directly hear what's in the letter she left for Luke. Alternatively,

If you look at it that way, Luke resembles Jessie in some way or the other. There could have been some untold story about Jessie that no one knows, mostly her getting pregnant at an early age before age 14, and Luke was the end product of it. Somehow, Jessie's father, trying saving face for his daughter's "secret shame", had Luke left on the orphanage when there's no one to take him. Years later, he was found by the Rosses and got adopted. Later on when Jessie started to work for them, she had no idea that Luke was her "missing son." (Idea for WMG here.)
  • Jessie was 18 at the start of the series. Luke was 10 or 11. So, no.

Bailey will appear on the series
And be revealed to be Jessie's Evil Twin

Creepy Connie is a cousin to Olive Doyle
Identical cousins frequently exist in the DCLAU

Alternatively the show takes place in the DCU
That's why Bertram's Butler's Association was going to roast Alfred Pennyworth and how Luke could so easily believe he was from Krypton. The Krypton thing had a precedent and since Gotham is supposedly in New York's neighbor state of New Jersey the Butler's Association could be regional.

Jessie is Bailey under Witness Protection/hiding for some reason
This theory's been a big part of the Fanon ever since the show began.

The whole show is the result of Bailey going through a It's a Wonderful Plot -type experience.
Someone or something is trying to show Bailey what her life would be like if she never tried to sneak onboard the S.S. Tipton. She would've stayed home and attended a regular high school, and then instead of college would've been stuck as a nanny with all of her attempts at big dreams ending in Failure Is the Only Option. It's meant to show that by attempting to sneak onboard and by befriending London, Zack and Cody, she would've learned to let go of her inhibitions and gain the life experiences she needs to be successful.

Jessie actually was possessed by the "evil" nanny in "The Whining."

Bailey either dropped out or got kicked out of Yale (or never attended in the first place)
So out of embarrassment she changed her name and her backstory (figuring that Texas is a lot like Kansas) and ran off to New York (or simply stayed in New York, as it conveniently was the last destination of the S.S. Tipton, reinforcing the "she never attended in the first place" theory). Not to mention lying she was in a military family, which her family isn't.
  • At the end of Graduation On Deck, Bailey lied to Cody about being accepted into Yale, but after finding out that Cody was also rejected, she felt so ashamed and embarrassed about the lie that she could never bear to tell Cody the truth. So she jumped ship right there after the S.S. Tipton was scrapped in New York City and stayed, changing her whole identity and eventually stumbling into the Ross family - all in an effort to hide from Cody due to the massive shame she feels.

The song/poem Zuri wrote in the Austin & JESSIE & Ally Cross Over is a message to Jessie to give up her dreams and remain as her nanny.
The first verse of the song is about someone who's gone off songwriting and working in a studio to the point where she might as well be just an imaginary friend. As the rest of the song goes, she comes back and they finally meet "face to face" again. Obviously this is a subtle message on Zuri's part that Jessie would be better off just staying with them.

How the series will end
It'll be some big day for Jessie, like her and Tony's wedding or something. She'll be late for some reason, so she'll have to take a cab. She forgets her purse and gets ejected from the cab (like in the pilot), which knocks her out. She wakes up in bed, in the process waking up London. She's actually Bailey, still on the SS Tipton, and the entire series was All Just a Dream, a la Newhart's finale. Might go over kids' heads, but it could still work.

Alternatively, Emma will get her own show after Jessie ends.
Peyton R. List is rapidly becoming a fan favorite (in much the same way as Ryan on Suite Life), so it's certainly a possibility.

Jessie is related to Sidney.
Be one hell of a twist wouldn't it?

A future episode will feature Jessie running into her doppelganger: Bailey Pickett
Just to prove that Bailey and Jessie are not the same character.

Jessie's best friend Darla will visit some day
And she will be played by Brenda Song!
  • Partially Jossed already, from a certain viewpoint - Word of God statements on Twitter have confirmed that it's in fact Jessie who will be visiting Darla in Texas in the Season 2 finale along with some hints that she may indeed be played by Brenda.
    • The Wiki says that Darla is going to be Alyson Ashley Arm but the wiki's proven to be very unreliable so far.
    • Also Jossed on Brenda being Darla, according to IMDb.

Debby Ryan secretly wishes she was Asuka
She dies her hair red, and then look at all the Hair Colors tropes that fit her character, especially the ones that happen to cross over to apply to Asuka or even anime in general.

Debby and the Jessie crew are Tropers
Look at the Headscratchers that were eventually addressed in their own episodes and other things in response to this article.

Shaylee Michaels from "Jessie's Big Break" is a Newtype.
Considering she has her own strength and can hear almost anything, She could be one... all that's missing was the advanced sense (Since she failed to know the truth about McD, it took Luke's recording for her to believe) and piloting a Mobile Suit.

Bertram and Jessie really are the Scuba Bandit and Sweetheart Bandit
And they don't even realize who the other one really is!

"Quitting Cold Koala" will be replaced with a brand new episode about Celiac's disease
Just like what happened with the Hannah Montana episode "No Sugar, Sugar"/"Uptight (Oliver's Allright)"
  • Jossed, they simply edited out the offending scenes (the episode eventually aired 7/5/13).

There will be another All Just a Dream episode
Disney is fond of forcing wish-themed episodes on non-fantasy-themed shows. It's pretty common for boys Luke and Ravi's age to wish their older sister was an older brother and quite feasible for them to film an episode like that.
  • Confirmed on a few points! There will be an All Just a Dream-themed episode (or something like) set to air July 26, and it will be a part of another Disney Channel theme weekend. The episode is titled "The Jessie-nator: Grudgement Day" and will be similar in plot to Suite Life on Deck's All Just a Dream episodes, "Starship Tipton" and "A London Carol".
  • At this point it's almost safe to say that any out-of-place episode pertaining to a theme event will turn out to be an All Just A Dream episode (there have been no less than two so far for each of Seasons 2 and 3).

Jessie Prescott's dad's name is Jesse Prescott
Debby revealed in a twitter about the Season 2 finale that we'll meet Jessie's dad, and that his name is "J.W. Prescott" along with "watch out for what the initials stand for." Really, it's not hard to put two and two together here.
  • Also, Jessie's middle initial is W., just like her dad's.
  • The J.W. stands for John Wayne.

Ravi K. Ross' middle name is KHAAAAAAN!
Because it would be too hard for a show like this to resist.

Spencer List will make an appearance on the show in some role
There seems to be a demand for it, at the very least.

There's a high chance now that Luke will win Jessie's heart.
With recent events in the show (which will not be spoiled), I think there might be a big chance for Luke to win Jessie's affections (at most, in the finale). Unless Tony decides to fix things...

Emma was a Hannah Montana fan. And Hannah inspired Kitty Couture.
Odds are, Emma saw when Miley took off her wig on Jay Leno, and learned Hannah was a fictional character, so she decided to get famous through a fictional alter ego herself.
It's Always Sunny in PhiladelphiaWMG/Live-Action TVJekyll

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