At What Point Did Roose Bolton Decide to Betray Robb

[Good Guy Garlan]

I might be wrong, but I somehow doubt the garrison/troops at the Dreadfort would follow Ramsay's orders blindly enough to provoke a small civil war in the North. So I think Roose left orders to kidnap Lady Hornwood, and he authorized the whole thing, hoping it would weaken Robb's position. It was a calculated risk for him: if things worked out for Robb in the South, Roose could always blame Ramsay and deny any involvement in the kidnapping/burning of Winterfell deal, like he did in aSoS when Cat confronted him about it. 

[Celtic Cross]

When Stannis' forces lost at Blackwater. It had huge implications on the Northern cause, and Roose knew that for possibly the first time since Robb arrived south the scales had tipped against their side.

[Universal Sword Donor]

I might be wrong, but I somehow doubt the garrison at the Dreadfort would follow Ramsay's orders blindly enough to provoke a small civil war in the North. So I think Roose left orders to kidnap Lady Hornwood, and he authorized the whole thing, hoping it would weaken Robb's position. It was a calculated risk for him: if things worked out for Robb in the South, Roose could always blame Ramsay and deny any involvement in the kidnapping/burning of Winterfell deal, like he did in aSoS when Cat confronted him about it. 

I tend to think Ramsay did the Hornwood acts on his own (so he wouldn't be a bastard anymore, but a lord). The sacking of WF, OTOH, I think has Roose written all over it. It's something like a month and a half after he had seized HH, he knew about Theon's betrayal, and there was plenty of time and ability for him to send a raven to the DF with general instructions.

[jarl the climber]

I tend to think Ramsay did the Hornwood acts on his own (so he wouldn't be a bastard anymore, but a lord). The sacking of WF, OTOH, I think has Roose written all over it. It's something like a month and a half after he had seized HH, he knew about Theon's betrayal, and there was plenty of time and ability for him to send a raven to the DF with general instructions.

Roose tells Theon that it was his taking Winterfell that brought about Robbs demise, I think we should take him at his word in this instance. Even if Stannis had won, it doesn't preclude Bolton from betraying him. 

[Artos Cold]

Once he realized that Robb was going to lose them the war and get them all killed. I think him marrying Jeyne was the last straw, but all the times Robb ignored his advice for sure added up to it

I think youre confusing the show with the books, in the books Robb splits his army in two and gives his foot to Roose who marches down to meet Tywin while Robb goes to Riverrun with his cavalry. They dont meet again until the Red Wedding. 

[BadWo1f]

I strongly doubt he wanted to betray Robb from the start, Robb was wining and Roose was in no position to betray him. I think he decided to do it once Tywin won against Stannis and alliance with Tyrells was formed. He will chose the best option for him, if Robb was wining, that was the best option for him, at the time. That silly marriage also triggered Roose.

[Wavey Sauce]

I think youre confusing the show with the books, in the books Robb splits his army in two and gives his foot to Roose who marches down to meet Tywin while Robb goes to Riverrun with his cavalry. They dont meet again until the Red Wedding. 

Correct. But Roose was still sending over what he thought should be done and Robb would ignore. Also even with him being away from Robb Roose was still able to hear of his mess ups

[Artos Cold]

Correct. But Roose was still sending over what he thought should be done and Robb would ignore. Also even with him being away from Robb Roose was still able to hear of his mess ups

Do we know for certain they were corresponding? 

[marsyao]

When Stannis' forces lost at Blackwater. It had huge implications on the Northern cause, and Roose knew that for possibly the first time since Robb arrived south the scales had tipped against their side.

I believe Roose started having second thought after the blackwater, but as long as the alliance of North and Riverland holds, King Robb still had a chance to have a reasonable negotiated peace, so blackwater and the fall of Winterfell alone were not enough to making Roose to betray Robb, but Robb's brainless stupid marriage and later his killing of Karstark made it clear that the Northern alliance would not hold, which means Robb and anyone stood with him would be destroyed in the way, and as a smart man, Roose would not go down with him and, by betraying Robb now, he even could have much to gain

[Lord Lannister]

Roose probably started thinking about it when Robb was declared king of the North and in earnest after the Blackwater. As close as he plays his cards though there's no real way to know precisely.

[Daendrew]

As soon as he was borne. Killing Starks is the Bolton family tradition.

[Wavey Sauce]

Do we know for certain they were corresponding? 

2 main commanders in the same army do tend to correspond. Almost goes without saying. But as Robb as king he is the one who would give orders of important things etc, it would be impossible during a war that they wouldnt correspond

[marsyao]

As soon as he was borne. Killing Starks is the Bolton family tradition.

Boltons haven't  killed no Starks for at least one thoustand years, before that Starks killed at leas as many Boltons as killed by Boltons

[thelittledragonthatcould]

Correct. But Roose was still sending over what he thought should be done and Robb would ignore. Also even with him being away from Robb Roose was still able to hear of his mess ups

This seems doubtful as Robb spent much of his time after Riverrun in the Westerlands. There seems no indication that Roose was being ignored or was particularly (publicly at least) displeased with Robb and his decisions.

"Someone must have the courage to say it," Ser Hosteen said. "The war is lost. King Robb must be made to see that."

Roose Bolton studied him with pale eyes. "His Grace has defeated the Lannisters every time he has faced them in battle."

Roose may well have been disappointed with Robb's decision making from close to the start, but there was no indication he was sharing these thoughts with Robb. he gave the impression that he completely supported Robb.

[Wavey Sauce]

This seems doubtful as Robb spent much of his time after Riverrun in the Westerlands. There seems no indication that Roose was being ignored or was particularly (publicly at least) displeased with Robb and his decisions.

"Someone must have the courage to say it," Ser Hosteen said. "The war is lost. King Robb must be made to see that."

Roose Bolton studied him with pale eyes. "His Grace has defeated the Lannisters every time he has faced them in battle."

Roose may well have been disappointed with Robb's decision making from close to the start, but there was no indication he was sharing these thoughts with Robb. he gave the impression that he completely supported Robb.

Was Roose fighting his own war? Calling all the shots? Of course they will speak and send messages, it is Robbs war he is the king, he wouldn't just put someone in charge of half his force and let set person do whatever they want without being on the same page

[thelittledragonthatcould]

Was Roose fighting his own war? Calling all the shots? Of course they will speak and send messages, it is Robbs war he is the king, he wouldn't just put someone in charge of half his force and let set person do whatever they want without being on the same page

No one is denying that there may have been some contact between the two men, though it would have been sparse considering that Robb was constantly on the move in the Westerlands, but your claim that Roose was offering advice to Robb and was being ignored. Zero evidence for that.

[BadWo1f]

As soon as he was borne. Killing Starks is the Bolton family tradition.

Starks killed Boltons as well, all of that happened very long time ago.

[Damsel in Distress]

So I'm not convinced that this was his plan from the very beginning. But I can't figure out when exactly he made this decision. I haven't exactly figured out the timeline. My guess is that he decided right after Robb married Jeyne. For me, it doesn't make sense that he would do this before is point because Robb was essentially winning. He definitely wouldn't initiate the plan imo.

 

What does everyone else think? Is there any evidence that I'm missing? I'm aware of the Duskendale thing so obviously it was determined well the Red Wedding but other than that what else?

Roose crossed over when he decided to let Jaime leave Harrenhal instead of taking him back to Robb Stark.  There was no going back for Roose from that point forward.  He has to kill Robb after that to preserve his own life.  Should Robb find out he helped Jaime escape, Roose would get the same punishment as Rickard Karstark but Catelyn gets off with treason unpunished.  There must have been an agreement between Roose and Jaime at Harrenhal.  Jaime had to know that Roose was betraying Robb in letting him go.  Jaime knew Roose would kill Robb and they could have planned it together.

[Lord Wraith]

Roose Bolton was seated by the hearth reading from a thick leather bound  book when she entered. “Light some candles,” he commanded her as he turned a page. “It grows gloomy in here." She placed the food at his elbow and did as he bid her, filling the room with flickering light and the scent of cloves. Bolton turned a few more pages with his finger, then closed the book and placed it carefully in the fire. He watched the flames consume it, pale eyes shining with reflected light. The old dry leather went up with a  whoosh, and the yellow pages stirred as they burned, as if some ghost were reading them. “I will have no further need of you tonight,” he said, never looking at her.

I always wondered what was in that book and whether or not it had something to do with Boltons betrayal?

[The Broke Howard Hughes]

Being an opportunist it was probably always in the back of his mind. He waited,  biding his time saw an opportunity an jumped. He probably made the actual decision when word spread that Theon killed Bran and Rickon. Ironically the smarter move on his part would have been to plan the RW with Walder and Tywin but inform the Northern Lords of the plan. It would have given you control of the bridge, dealt with the Freys and showed all of Westeros AGAIN that Tywin Lannister is just a man. Beating him militarily and politically,  even just the once would be enough to show everyone he's not invincible. This would have endeared Roose to everyone in the North given his house some prestige and in return he could have gotten almost anything from Robb. Including Sansa. He could have then bide his time and likely came up with a plan that didn't ensure his eventual murder by the same men he hoped to rule. By betraying Robb he doomed himself to that exact same fate. The RW seemed like a good idea at the time but everything had to go exactly right, and of course that never happens.  Roose likely always had ambitions to be the man and that ambition trumped his common sense. Had he asked himself what if... He would have seen clearly that Tywin was using him, and not only that he was giving him something he planned on taking away almost immediately (Warden of the North). And if he'd work behind a defiant Robb's back with you to solve his problems why wouldn't he do the exact same thing with you when you didn't follow his orders? It was a foolish plan start to finish. A dream his family has likely had for a thousand years that he saw an opportunity to fulfill but didn't think through. First sign of weakness he broke ranks and went rogue, a few months, maybe a year of power, but ultimately the end of house Bolton.