SPOILER Why was Robb Stark killed
When did the traitor turn around?
"When" is a good question. I think the answer is Roose plans all the time. When Robb called the Banners, Roose was probably going through his options and trying to make the most of the situation.
Spoiler ADWD below
We get a glimpse of Roose's thoughts through Lady Dustin, who claims that Roose is a psychopath who has no feelings and likes to manipulate people for his own pleasure. Even so, Roose likes to stay "under the radar" and let others take the blame while taking advantage of it. Walder Frey, for example, certainly assumed most of the blame for the Red Wedding, although I suspect Roose Bolton was the bigger culprit (he personally killed Robb).
It's like Jaime said in ASOS (paraphrase) - that every lord has recalcitrant flagmen who envy their power. Tywin had the Tarbecks, the Tyrells had the Florents, host Tully had Walder Frey, Ned Stark had Roose Bolton. Strength is the only thing that keeps such men in check. And when they smell weakness, they turn around.
Spoiler ADWD below
Roose Bolton himself told Theon in ADWD that he had to thank him for winning the North. The Stark house was ready when Theon dismissed Winterfell. This was almost certainly not the time he was planning treason, but it would have encouraged him to move on with his plans. We also don't know if Roose and Ramsay intended to attack Winterfell, or if Ramsay did it on his own initiative and Roose felt compelled to hold out. We know Roose sees Ramsay as his only option for House Bolton to survive (unless he lied to Theon about it in ADWD).
Roose was in the possession of many important hostages and the leader of large armies. Above all, of course, he found Jaime, who opened a dialogue with Tywin. He also got his hands on the Frey boys in Winterfell, which he undoubtedly used as a lever against Walder Frey. He sent Robett Glover and Ser Helman Tallart to ambush Duskendale, where they were ambushed and defeated by Randyll Tarly and Gregor Clegane. No doubt this was done on purpose to kill Stark loyalists. He's done a couple of maneuvers like that.
It is interesting to note that Roose would never have believed he could conquer the north on his own behalf, he is too realistic for that: the north would never support Ramsay or a Bolton, only a Stark. Because of this, you couldn't see that he was directly involved in the Red Wedding and why fake Arya was so important to his plans.
When Roose started planning it, I think the answer is, he always planned it. It was just a matter of when he could do something about it, when he was given opportunities, and when Robb showed weakness.
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