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Jefferson's hat 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
Jefferson and Regina jump through the hat. ("Hat Trick")
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. ("The Doctor") 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. ("Out of the Past") 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. ("Hat Trick") 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. ("Queen of Hearts")
After the Curse
Regina seeks out her poisoned apple. ("An Apple Red as Blood")
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. ("Hat Trick") 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. ("An Apple Red as Blood")
The hat is destroyed by Spencer. ("Child of the Moon")
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. ("Broken") 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. ("We Are Both") 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. ("Child of the Moon")
After the Third Curse
TBA ("The Final Battle, Part 1")