Running from the Battle of Ice.

[The Sleeper]

Let's take at least one aspect of the Pink Letter at face value. Ramsay had reason to believe that Jeyne and Theon were at Castle Black. They are not. There two questions that arise. Why does Ramsay believe they would be there? Particularly because Theon was last seen impersonating a tapestry and was marked for either a beheading or a barbecue. And second, where are they?

One assumption we must make is that Ramsay believes that Jeyne's impostesure to be intact, because otherwise the letter would be 

The simplest answer to the first question is that Ramsay simply assumes that they would be there because he thinks of Jon as Stannis's ally and the latter has stashed important persons with Jon. The other option is that he has gotten actual information. Option one: he made his inferences from the spearwives and/or Mance. This could be the case. All of the info in the Pink Letter could have been provided by Mance along with the assumption that both Jeyne and Theon were heading straight to Castle Black. Option two: he interrogated some Umber outside of Winterfell. They might have misled him to believe that both Theon and Jeyne were heading for Castle Black, but they would not have much information about Stannis. Option three: he made contact with an ally from Stannis's camp, either a secret ally or a prisoner he interrogated. A lot of the information could have been gotten out of such person but it would still leave the question of why he thought Theon would be at Castle Black. Option four: he ransacked Stannis's camp. In terms of information this is a more problematic scenario than it first appears. While he would potentially get out know everything, there is no guarantee that the right people who know stuff would be captured alive, there would be contradictory accounts and sorting through all that would take time and have uncertain results. 

On the other hand there definitely four named individuals that were supposed to leave for Castle Black. Jeyne Poole, Alysanne Mormont, Justin Massey and Tycho Nestoris. They were also supposed to leave immediately after Massey took his leave from Stannis. So if things went according to schedule they indeed should have been in Castle Black, by now. It might be very important that only Jeyne is mentioned in the letter. After all Mormont, Massey and particularly Nestoris are all important in their way. The first possibility is that they simply floundered in the snow and are simply late or maybe lost or dead. The other option is that they deviated from their course. Massey and Nestoris need to get to Braavos. But how were they supposed to get there? There are after all no ships currently in Eastwatch. White Harbor is likely to be considered hostile territory and in general heading to the East would be a long arduous journey through hostile territory. Would they know that? Nestoris signed off on the use of the Braavosi ships for the Hardhome mission, so he may expect his ride not to be there. Another reason they changed destinations would be simple prudence. If the battle went ill after all, or even if it didn't, people could be after them. Or even some one who escaped from he battle caught up with them and warned them that Ramsay was looking for them. Long story short they could be somewhere in the woods heading for parts unknown. And Theon is in the wind. 

[aryagonnakill#2]

11 hours ago, The Sleeper said:

Let's take at least one aspect of the Pink Letter at face value. Ramsay had reason to believe that Jeyne and Theon were at Castle Black. They are not. There two questions that arise. Why does Ramsay believe they would be there? Particularly because Theon was last seen impersonating a tapestry and was marked for either a beheading or a barbecue. And second, where are they?

One assumption we must make is that Ramsay believes that Jeyne's impostesure to be intact, because otherwise the letter would be 

The simplest answer to the first question is that Ramsay simply assumes that they would be there because he thinks of Jon as Stannis's ally and the latter has stashed important persons with Jon. The other option is that he has gotten actual information. Option one: he made his inferences from the spearwives and/or Mance. This could be the case. All of the info in the Pink Letter could have been provided by Mance along with the assumption that both Jeyne and Theon were heading straight to Castle Black. Option two: he interrogated some Umber outside of Winterfell. They might have misled him to believe that both Theon and Jeyne were heading for Castle Black, but they would not have much information about Stannis. Option three: he made contact with an ally from Stannis's camp, either a secret ally or a prisoner he interrogated. A lot of the information could have been gotten out of such person but it would still leave the question of why he thought Theon would be at Castle Black. Option four: he ransacked Stannis's camp. In terms of information this is a more problematic scenario than it first appears. While he would potentially get out know everything, there is no guarantee that the right people who know stuff would be captured alive, there would be contradictory accounts and sorting through all that would take time and have uncertain results. 

On the other hand there definitely four named individuals that were supposed to leave for Castle Black. Jeyne Poole, Alysanne Mormont, Justin Massey and Tycho Nestoris. They were also supposed to leave immediately after Massey took his leave from Stannis. So if things went according to schedule they indeed should have been in Castle Black, by now. It might be very important that only Jeyne is mentioned in the letter. After all Mormont, Massey and particularly Nestoris are all important in their way. The first possibility is that they simply floundered in the snow and are simply late or maybe lost or dead. The other option is that they deviated from their course. Massey and Nestoris need to get to Braavos. But how were they supposed to get there? There are after all no ships currently in Eastwatch. White Harbor is likely to be considered hostile territory and in general heading to the East would be a long arduous journey through hostile territory. Would they know that? Nestoris signed off on the use of the Braavosi ships for the Hardhome mission, so he may expect his ride not to be there. Another reason they changed destinations would be simple prudence. If the battle went ill after all, or even if it didn't, people could be after them. Or even some one who escaped from he battle caught up with them and warned them that Ramsay was looking for them. Long story short they could be somewhere in the woods heading for parts unknown. And Theon is in the wind. 

The village where Stannis is located is only 3 days ride from WF, even including a day of battle and 3 days back to WF is the 7 days mentioned in the letter.  On the other hand it is a long way from Castle Black.  I don't think there is any inconsistency in that timeline.

[The Sleeper]

8 hours ago, aryagonnakill#2 said:

The village where Stannis is located is only 3 days ride from WF, even including a day of battle and 3 days back to WF is the 7 days mentioned in the letter.  On the other hand it is a long way from Castle Black.  I don't think there is any inconsistency in that timeline.

You're right, in that Ramsay could well have sent the letter ahead of the party. We know from Tyrion's chapter way back in games that it is more than eighteen days from Winterfell to Castle Black and in what should have been better conditions. But if Massey left as planned the party should have the full measure of time between Theon's and Jon's chapters to arrive at Castle Black and it is not like the raven would have teleported. Ramsay, however sounds like he was frothing at the mouth when he wrote the letter, so it is not out of the question that he would send the letter ahead of the party. 

It does seem that Ramsay expected to find them there (after all, how would Jon know what Reek is) and that they would have too much of a head start for him to send people after them. Or that he couldn't for whatever reason.