Jefferson's Hats

Jefferson's Hats is a magical hat which possesses the ability to open portals to lands with magic; however, there is a condition - only the amount of people who travel through the portal are allowed to make the return trip, so if one person goes through, only one can return, and if two go through, two return, and so on.

It was owned by Jefferson, who was often employed by Rumplestiltskin to travel to various lands, until he decided to give up world-crossing to care for his daughter, Grace. The Evil Queen tricked it into her own possession, but eventually it was thrown onto a fire by Albert Spencer to prevent David Nolan from reuniting with his lost family.

Before the Curse
Rumplestiltskin employs Jefferson to use his hat to go to Oz in search of both a crystal ball and a pair of silver slippers; however, he is only able to retrieve the ball. He proceeds to find a mopey Regina, still grieving for the loss of her true love Daniel, and offers to bring her Viktor Frankenstein - a man who can supposedly bring back the dead. As it turns out, this is all a ploy organized by Rumple. Viktor fails on purpose so that Regina will finally move on, and Jefferson uses his hat to return the doctor to the Land Without Color.

Jefferson decides to give up world-crossing following the death of his wife, Priscilla, in Wonderland; instead, he opts to raise his daughter Grace, a stores his magical hat in a hat box for safe-keeping.

Queen Regina shows up at Jefferson's hovel, in need of the hat. He refuses to help her until he realizes how his poverty is affecting his daughter, and so he brings the hat to Regina on the condition that his daughter will want for nothing. He explains the rules - how if the two of them go through, only two can return - and they set off for Wonderland via the Hall of Doors. However, Regina wants to go there to rescue her father. She leaves Jefferson stranded while she and Henry go back to the Enchanted Forest. Jefferson spends years trying to create another magical hat so that he can make it back to his daughter, but this drives him insane.

Regina holds on to the hat and gets Captain Hook to use it to head to Wonderland and kill her mother, Cora (also known as the Queen of Hearts). He takes the dead body of Claude with him so that he will be able to bring Cora's body back in return, but when she learns of what her daughter has planned, she fakes her own death, going through the hat with Hook while beginning a plot of her own.

Season 1
After the casting of the Dark Curse, Jefferson is punished by retaining his memories in Storybrooke while not being allowed to see his daughter. He kidnaps Emma Swan because he believes her to be magical, and gets her to make him a new hat. It is left ambiguous as to whether or not she is successful.

When Regina needs a way to get rid of Emma Swan without killing her, she leaves a White Rabbit playing card on the bike of Jefferson's daughter so that he will see it and seek her out. She reveals that she still has his hat, and needs him to use it for her (in exchange for new memories). He cannot do so because they are in a Land Without Magic - but Regina has some magic stashed away in her vault. She takes him down there and puts a few trinkets into the hat, but it's not enough. She is then forced to part with her magical engagement ring, which bares Daniel's face, but even this only creates a portal big enough to retrieve a mere object. Regina realizes that she can get her poisoned apple, and she successfully snatches it from out of the past, then needing a way to figure out how to get Emma to eat it.

Season 2
When Emma breaks the curse, Mr. Gold simultaneously brings magic to Storybrooke, which allows him to summon the Wraith to gives Regina a fate worse than death, in penance for locking up his true love Belle. To get rid of the Wraith, Regina and the Charmings try using Jefferson's hat to banish it to some far-off realm. Emma recognizes it immediately for what it is, but Regina plays dumb, going on to try and open a portal as the Wraith is battled. She is unsuccessful - at least until Emma touches her shoulder - but then the Wraith goes after her. Emma pushes her out of the way as the Wraith is sucked into the portal, but it thus thinks that she is Regina and drags her down with it. Unable to lose her daughter again, Mary Margaret follows. David tries to do the same, but the portal closes before he can do so, and he instead squishes the hat while his family remain in what's left of the Enchanted Forest.

David gets a locator spell from Mr. Gold and uses it on the hat, leading him to Jefferson. Jefferson tells him a little about it, but ultimately runs away. Grumpy and the other dwarfs begin mining fairy dust in order to power it and bring Snow and Emma home.

The dwarfs find magic diamonds in the mines and Mother Superior begins distilling them into fairy dust to power the hat - however, Albert Spencer (previously King George) steals it and throws it on a bonfire in order to gain revenge over David.

Season 6
After the Black Fairy's Dark Curse banishes Zelena back to Oz, where she notices the land is fading out of existence, she somehow finds one of Jefferson's hats and uses it to help herself, her daughter, and some of the munchkins escape to the Enchanted Forest. She then reaches Regina's old palace and brings her sister and the other heroes into the hat's portal of doors to show them that, besides Oz, various realms are also disappearing for an unexplained reason. Through discussion, they figure out the magic sustaining the worlds is dying out because Emma's belief is depleting. Later, other residents from a number of realms arrive into the portal of doors, presumably through the use of one of Jefferson's many hats. As Regina comments to Zelena about seeing an Arendelle native with fresh snow on his shoulders, Jasmine and Aladdin greet the heroes, having just escaped from Agrabah. As the Enchanted Forest begins collapsing because of Emma's fading belief, Regina teleports everyone out of the hat and to her palace so she can work on a way back to Storybrooke.

Trivia

 * According to the Mad Hatter, the number of people that go into the first hat must come out. He explains it as a rule for the hat, not for a world. Otherwise, the circumstances of Jefferson, Dr. Frankenstein and Rumplestiltskin's travels from and to the Land Without Color have yet to be explored.
 * However, the second hat appears to forgo this rule, with numerous people fleeing their dying worlds and escaping into the Portal of Doors.
 * The first hat was able to travel in time between Storybrooke and the Enchanted Forest during the Dark Curse.
 * Rumplestiltskin states the hat can only reach worlds with magic. Therefore, travelling to the Land Without Magic via the hat is impossible. {{E|The Doctor")
 * Zelena later notes this rule applies to the second hat as well.
 * The walls and floor on the storybook page with the door, which Henry finds, have the same design as the inside of the first hat. {{E|Unforgiven}}
 * A door inside the second hat features the same motif as the floor in Hades' Lair: a pentacle with pitchforks at the edges. {{E|The Final Battle Part 1}}
 * The Triangle Pattern Door greatly resembles the triangle patterns on the domes and walls of Jasmine's Palace in Agrabah. {{E|The Final Battle Part 1}}
 * Another door carries the same insignia as the thrones in the DunBroch Castle. {{E|The Final Battle Part 2}}

TBA {{E|The Final Battle, Part 1}}