[ADwD Spoilers] Does Roose know what Ramsay did?

[alienarea]

I like the OP's analysis and the idea that Roose's statement about boy lords being a bane is going to bite him in the end is definitely something that GRRM would come up with.

[Meddler]

In regard to the Freys at Winterfell--it's pretty easy to construct a reason that Ramsay would want to keep them alive even if Roose didn't order the sack. Little Walder is Fat Walda's brother. It's possible, even likely, that in communicating simply regarding the status of Winterfell, Roose specifically asked after the boys at the request of his wife.

However, it's pretty easy to establish that it's unlikely Roose was even communicating directly with Ramsay. He may have ordered his garrison at the Dreadfort to do something like sack Winterfell, but even that is implausible.

The first problem is that Ramsay is believed to be dead. This report comes from Rodrick Cassel, who also takes "Reek" prisoner. "Reek" has no way of communicating with Roose, so Roose has no opportunity to receive a report to the contrary. If he was in communication with the Dreadfort, it wasn't with Ramsay. The first opportunity he would have to communicate with Ramsay is after Theon releases "Reek" and he returns to the Dreadfort. This brings us to the second problem....

....the timeline. The timelines of various events can be difficult to synchronize, but it does not appear possible that the Sack of Winterfell could have been part of the Lannister/Frey/Bolton plan to betray the Starks. The Sack happens at the end of ACoK. This is roughly around the same time as the Battle of the Blackwater. No one has yet received word of Robb's marriage in King's Landing as far as we know. Unless the timelines are highly out of synch at this stage, Robb is concurrently still on his campaign in the Westerlands, which ends with the Battle of the Crag. During the Battle of the Crag, Robb takes a wound, is nursed back to health by Jeyne Westerling, sleeps with her, then marries her. Even after that, it takes time for news to reach Riverrun, which is much closer to the Crag than King's Landing, the Twins, or even Harrenhal. It is also the precipitating event of the Frey's betrayal, and the Freys have every motive to support Robb prior to his marriage with Jeyne. It's also worth emphasizing: The Lannisters still consider Robb Stark a threat leading up to the Blackwater. Roose has to take Harrenhal after Tywin abandons it by cunning and force, Tyrion has no knowledge of Robb Stark's marriage, and Tywin isn't observed writing the letters that preceed the RW until after he claims the Handship in KL. This means the RW could not have been planned prior, and it is not likely Roose would have ordered such an aggressive act against the Starks as Sacking Winterfell independently. Even if it somehow promotes a personal agenda regardless of the Freys and Lannisters, it's incredibly risky, and Roose is far too cautious to make such a bold move without support.

The third problem is lines of communication. Ordering the Sack of Winterfell from Harrenhal, surrounded by Robb's supporters, while sitting on contested ground, by sending a Raven into the North, more contested ground with a population predominantly in support of Robb, is almost as risky as committing the Sack itself without support, and very out of character for Roose. When Lysa Arryn sends "news" of the Lannister involvement in Jon Arryn's murder, she doesn't send a raven, she sends a rider, all the way down from the Vale, up through the Neck and into the North, and this is during peacetime. Roose doesn't have this option. Moat Cailin is held by Ironmen, so the lines of ground communication are cut off. That leaves one option--sending a message by ship. This would most likely entail sending someone to Maidenpool or Saltpans, have them find a ship bound preferably for White Harbour (Eastwatch would work too but it's a longer journey) and then have them travel from there to the Dreadfort. This would not be a swift journey, and we also know the weather on the narrow sea is not forgiving at this time. The amount of time between news of Robb's marriage reaching Roose and the Sack of Winterfell would have to be rather large, almost impossibly so.

My thinking is that Ramsay must have arrived at the Dreadfort with his own plans for Winterfell. While he was there, he learned of his father's marriage and Roose's concern over the Walders. Even if Roose's marriage may present a hurdle for him down the line, he's not yet been legitimized and must become so before even considering the issue of inheritance, and even in that case, it would be Walda's children that would pose a problem, not her brother and distant cousin, who could even serve as potential allies if a domestic squabble does ultimately arise.

[VaramyrSixchins]

You bring up some fair points regarding the logistics of communication. The only stickler in your analysis for me is the inference that Robbs wedding was the deciding factor in Roose's decision to turn. It wasn't. He was weighing his loyalties as far back as GoT. If anything, Theon taking WF in the first place was his deciding factor. As he tells Theon "The Starks were done & doomed" when WF fell.

Your thoughts have made me question the timeline, however. Does anyone remember which battle the Hornwood heir was killed in? Was Roose in the same battle? Could he have been in communication w Ramsay @ this point, exploring their options on exploiting the war's events?

[Meddler]

You bring up some fair points regarding the logistics of communication. The only stickler in your analysis for me is the inference that Robbs wedding was the deciding factor in Roose's decision to turn. It wasn't. He was weighing his loyalties as far back as GoT. If anything, Theon taking WF in the first place was his deciding factor. As he tells Theon "The Starks were done & doomed" when WF fell.

Your thoughts have made me question the timeline, however. Does anyone remember which battle the Hornwood heir was killed in? Was Roose in the same battle? Could he have been in communication w Ramsay @ this point, exploring their options on exploiting the war's events?

It's not so much that I doubt Roose's lack of true loyalty to Robb prior to the Frey betrayal, it's that I doubt he would have sacked Winterfell without the support of the Freys and Lannisters, and we don't have any indication he had the support of either at the time. He might have designs on finding allies to use to overthrow Winterfell at some point if the opportunity arose, but directly ordering such an aggressive action prior to securing these alliances is out of character. Meanwhile, we don't need an order from Roose to give Ramsay motive--we know Ramsay is ruthless and more impulsive, and he was angry after his altercation with Rodrick Cassel.

Your second point is interesting though. Lord Halys Hornwood did die with Roose Bolton, at the battle of the Green Fork. This is also before the Ironmen came down on the North, so Moat Cailin was passable and Ramsay was probably still at the Dreadfort, meaning they very well could have been in contact. There was a male heir to Hornwood that wasn't with Roose though--Daryn (who we later find out was betrothed to Alys Karstark), who was slain by Jaime Lannister at the Whispering Wood in Robb Stark's contingent.

The idea that Roose played a role in what happened at Hornwood is definitely interesting, even likely perhaps. If anything, Roose and Ramsay may have discussed possible outcomes from the war, and the Hornwood would almost certainly have come up in this discussion considering it's proximity to the Dreadfort. Directly ordering a sack of Winterfell so early in the sequence of events still seems out of character for Roose (though not for Ramsay), but it's possible Roose planted the idea and was prepared to take such action if things got any worse (as we know they did). It actually probably benefits him if he didn't give the order, or at least can't be tied to it, as it's some manner of potentially saving face if (when) the information comes out and he has to scapegoat Ramsay, as others have suggested.