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Major spoiler for season 3 of GOT:

Lord Bolton betrays the Starks by returning Jamie Lannister to Kings Landing and then assisting in the massacre of the Starks by the Frays. In return, he is made Warden of the North (at least in the hypothetical Lannister victory version of the post war Westeros). Bolton had earlier served with distinction under Robb Stark, including leading the attack in which Jamie Lannister was captured in the first place. At what point did Bolton turn? How long had he been plotting with the Lannisters?

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"When" is a good question. I think the answer is that Roose plots all the time. When Robb called the banners, I think Roose went through his options and thought about how to gain the most from the situation.

Spoilers ADWD below

We get some insight into Roose's mind through lady Dustin, who claims that Roose is somewhat of a psychopath, who has no feelings and likes to manipulate people for his own amusement. Even so, Roose likes to stay "below the radar", let other people take the blame while he reaps the benefits. Walder Frey certainly took most of the blame for the Red Wedding, for example, though my hunch is that Roose Bolton was the bigger culprit (he did personally kill Robb).

It is as Jaime said in ASOS (paraphrasing)-- that every lord has unruly bannermen who envy them their power. Tywin had the Tarbecks, the Tyrells have the Florents, Hoster Tully has 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.

Spoilers ADWD below

Roose Bolton himself told Theon in ADWD that he had him to thank for winning the North. That house Stark was done when Theon sacked Winterfell. That was almost certainly not when he started plotting betrayal, but it would have encouraged him to set his plans in motion. Also, we do not know whether Roose and Ramsay planned to attack Winterfell, or if Ramsay did it on his own initiative and Roose felt compelled to see it through. We do know that Roose considers Ramsay his only option for house Bolton's survival (unless he lied to Theon about that in ADWD).

Roose found himself in possession of many important hostages, and the leader of big armies. Most notably, of course, he found Jaime which opened a dialogue with Tywin. He also got his hands on the Frey boys in Winterfell, which he no doubt used as leverage against Walder Frey. He sent Robett Glover and Ser Helman Tallart to raid Duskendale, where they were ambushed and defeated by Randyll Tarly and Gregor Clegane. No doubt this was done intentionally in order to kill off Stark loyalists. He did a few such manoeuvres.

It is interesting to note that Roose would never have believed he could take the north in his own name, he is too much of a realist for that: The North would never support Ramsay, or a Bolton, only a Stark. Which is why he could not be seen to be directly involved in the Red Wedding, and why fake Arya was so important to his plans.

So, as for when Roose started planning it, I think the answer is: He always planned it. It was just a question of when he could start doing something about it, when he was given opportunities and when Robb showed weakness.

  • Some spoiler tag for the ADWD part maybe ? I almost read it unwillingly :p – Kalissar Jun 13 '13 at 10:56
  • @Kalissar The book has been out for 2 years now, read it already. :P I'm not sure which part would be the spoiler... all of it? – TLP Jun 13 '13 at 11:03
  • The book may have been out for a time, but the series has not quite caught up with the books yet and the question is tagged game-of-throne (the series tag! the books tag is a-song-of-ice-and-fire) so I think it's relevant to put some spoilers, at least for the paragraph that begins with "Roose Bolton himself tells Theon in ADWD..." – Kalissar Jun 13 '13 at 11:07
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    @Kalissar What I mean is that if you like this series and fear spoilers you should just stop living dangerously reading internet forums and just go read the books. Its not like you haven't had time to do so, and at a certain point, you have to stop blaming others for that which you yourself is to blame. On a related topic: Yes, spoiler tags was a good idea, I added some. And no, this tag is for the book AGOT and the TV-show, read the hover text. – TLP Jun 13 '13 at 11:24
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    @TLP Check out this SSM for The George's take on this matter. – Möoz May 5 '15 at 23:30
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In the books it's suggested that Lord Bolton may have been planning something sinister from an early stage. Certainly before the battle of the Green Fork (the diversion he created so that King Robb could cross the Twins and liberate Riverrun). It was noted that during that battle only men loyal to House Stark were killed, while the men loyal to Bolton survived.

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    good spot. The hints are definitely there, albeit they are clearer in hindsight. One scene that sticks out in my mind is where Robb and his mother are discussing strategy for his campaign, and the diversion plan. Initially Robb wants to send the Greatjon to face Tywin: "he's always saying he would smash Tywin, let's give him the chance". However, his mother points out that the Green Fork will require cold calculation and cunning, not just brute strength and bravery. Immediately, Robb changes his mind: "Roose Bolton. He frightens me". – The Giant of Lannister Jun 13 '13 at 19:30
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Early.

I used to wonder this myself, and there are actually a lot more very subtle details in the books that make me think he was never truly loyal to the Starks.

As System Down notes in his answer, the battle of Green Fork is the first hint. So we cannot know for sure, but the doubt exists.

In the series, remember what happens to Winterfell ? I won't put it in spoiler tags because the question is a season 3 spoiler level, so the reader who reads my answer should have already watched it. After Robb offer to all the Ironborn (except Theon) mercy if they surrender, one of Theon's men knocks him out (after the great speech) and the next thing we know is that he's tortured by Ramsay Bolton.

It's clearer in the book : Winterfell is under the siege of Robb's bannermen (they want to take it back) but Roose Bolton sends his bastard Ramsay to infiltrate the bannermen and kill them (since the bannermen will think the bastard's been sent to help them, for he is on Bolton's side, who they think is loyal to Robb). After this, Ramsay burns Winterfell and takes Theon to torture him, too.

This is definitely treason. So, at least, he was already turned when Winterfell was burnt.

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I believe he was loyal to Robb's cause in his own way up until the Blackwater. He obviously kept his own troops in reserve during the majority of the war, but his military decisions were done with a tactical competence. He tried to catch Tywin by surprise on the Green Fork by marching through the night and attacking at dawn. He also recruited the Brave Companions and orchestrated the taking of Harrenhal with no casualties.

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