The Winds of Winter: Who wrote the letter that killed Jon Snow?
Did Wyman Manderly write the Pink Letter?
Wyman Manderly is the obese lord of White Harbor, and he is in command of more men than any other northern lord. The Bolton hold over the North is heavily dependent on the resource-rich Manderlys being on their side. But we know that the Manderlys are attempting to undermine the Boltons and reinstall the Starks as the Lords of the North.
In one of Davos Seaworth’s chapters from Dance, he arrives in White Harbor to try and get the Manderlys to support Stannis. At first he seems unlikely to succeed, as the Freys are already there and the Manderly family seems to be fully behind the Bolton-Lannister-Frey alliance. Much to his surprise, Davos is taken to a secret meeting with Wyman Manderly and Robbett Glover where they reveal their knowledge about Ramsay Bolton burning Winterfell and that Bran and Rickon Stark are alive. While they do not not know location of Bran, they know that Rickon was taken to the island of Skagos by the wildling Osha. Lord Wyman tells Davos that he will support Stannis Baratheon as his king if Davos safely retrieves Rickon from Skagos; Wyman’s intention is to make Rickon the Lord of Winterfell after they defeat the Boltons.
Cut to the end of Dance, and Wyman and the Manderly army are among the northern men at Winterfell. The Boltons are struggling to keep order. The Manderlys and Freys come to blows when a character named Little Walder Frey is found murdered. Someone even slashes at Wyman’s throat during the fighting. Roose Bolton announces that he is sending the assembled army to fight Stannis, and that the Freys and Manderlys will march separately to avoid any more infighting. This puts the Manderlys in the perfect position to help Stannis defeat the Boltons.
So with all of this in mind, why would Wyman write the pink letter? If Stannis is defeated or Davos’ mission to get Rickon is unsuccessful, Jon Snow could be a backup plan for Wyman. He may have written the letter with the intention of making Jon the lord of Winterfell.
Or it could go deeper than that. Wyman not only knows Jon was raised by Ned Stark, but he could know that Jon is secretly the trueborn son of Lyanna Stark and Rhaegar Targaryen. Robbett Glover is the brother of Galbart Glover, who is currently in the Neck with Howland Reed. Reed just so happens to be the only living person who was at the Tower of Joy when Lyanna Stark gave birth to Jon Snow. There is a theory that the northern lords know about Jon’s lineage, and Wyman writing the letter could be their attempt at getting Jon to willingly leave the Night’s Watch to realize his destiny as the true King of Westeros.
I think this is a fairly likely scenario, especially because the Manderlys and other northern lords know how cruel the Boltons are, and about their participation in the Red Wedding. Wyman’s son died at the Red Wedding, and most every lord in the north probably had family members either killed or imprisoned there, not to mention the murder of their king Robb Stark. They are no doubt eager to get revenge and restore the dominion of their true liege lords, the Starks. And if they know that Jon is a true born half-Stark half-Targaryen, who better to lead them?