Who will win the battle of Winterfell?

[Damar]

What I find interesting about this battle is that it's a total coin toss on who will win, as both sides have enough advantages to make for a believing victory, and it all depends on who GRRM wants to win in accordance with how he wants the story to proceed.

[VaramyrSixchins]

Roose and Ramsay are doomed, doomed, doomed.

1. Stannis holds all the tactical "cards".He has a secure base at the Wall, the northern clan's allegiance, the grudging fealty of a force of wildlings at the Gift, he knows of the Karstark betrayal, he has a fresh influx of resources from the Iron Bank, both Greyjoy heirs, and most importantly, "Arya". More on this below.

2. Manderly/Umber Fifth Column. In aCoK, Manderlys/Umbers were ordered to work together to build boats. We know from Davos chaps that the boats WERE built, and that Manderly's raising men. Therefore, an open channel of communication between the Manderlys/Umbers existed, and still does. We also know from Cersei in aFfC that at the time the Umbers threw in with Ramsay, Moat Cailin was still held by ironmen and that Lord Manderly had "killed" Davos. We know from Stannis in aDwD that when the Umbers came to him, Moat Cailin was still held by ironmen. In short, we see a split Umber allegiance, unknown to the Iron Throne, that happened AFTER Manderly "proved" his loyalty but BEORE Roose joined with Ramsay. For the remainder of this post, I'm referring to them as the Mumberlys, cause they are one in their goals, and have been for a while.

3. Manderly is the master of whispers. Manderly tells Davos that a) the Stark kids are alive, B) He knows it was Ramsay, not Theon, that sacked Winterfell (having learned these things from Wex) and c) the Bolton's played a part in the RW (how he knows this he doesn't say). The only Bolton "secret" he doesn't mention is "Arya's" identity, but as the always brilliant poster tze points out in another thread, his request of "Brave Dany Flint" at "Arya"'s wedding indicates he knows that secret, as well. It's a sure bet that Manderly has told these secrets to at least the Umbers, if not more northmen. Glover knows as well. If the northmen think he can be believed, Theon can confirm all of the secrets, which is one of the reasons the letter demands he be returned.

4. The pink letter is 99% lies. The logical inconsistancies have been cited already, so I won't go into them here. but the bottom line is that only the bit about Mance and the spearwives holds water.

5. The importance of "Arya" and the true purpose of the letter. Numerous times, the point is made in aDwD that the Bolton's claim rests with "Arya", that the northmen would turn on the Boltons in an instant without that marriage. Indications are that many northmen know "Arya" isn't Arya, but they can't call B.S. for a variety of reasons. From the Bolton's view, someone calling B.S. is a bigger threat to their northern supremacy than Stannis's army could ever be. Losing her is a defcon 5 disaster, but the only thing worse is her escaping to someone who has the both the firsthand knowledge and the political neutrality to be able to call B.S. Someone like Jon Snow, the last son of Eddard Stark. Who would call him a liar if he proclaims "Arya" a fake? Therefore the letter is simply Roose's last desperate attempt at blackmail to ensure Jon's silence. "Tell the north about my bride, I tell the north about Mance. Oh, and your ally is dead. You're alone." Obviously it didn't work. Just as obviously, to me anyway, is that the letter was an unintended byproduct of Stannis/Mumberly's deception. Which brings me to:

6. The Battle of the Ice. If we take for granted Mumberly collusion, we see that the Freys are caught between two northern allies under the walls of Winterfell. I don't like their chances. We know that "Arya" made it somewhat safely, sans nose, to Stannis, which means the Boltons must hold the allegiance of the northmen in WF while keeping her escape secret somehow with her rescuer supposedly in a cage for "all the north to see." I don't like their chances. In order for the Bolton's Karstark ace-in-the-hole to be played, Karstark has to escape captivity and order his men to turn. I don't like his chances. Then the Boltons, with only Dreadfort men, must defeat the entire north, plus Stannis. I don't like their chances.

I believe the conventional wisdom about the Mumberlys killing the Freys and revealing themselves to Stannis will hold true, and this will set in motion the "Stannis is dead" subterfuge in the pink letter. I see a march on Winterfell and the northmen inside slitting some throats and opening the gates.

As to Lord Varys's point that Ramsay would seek confirmation of Stannis's death before acting, I think it's worth remembering that Stannis has captive Karstark, someone who the Bolton's believe is an ally, and the Dreadfort's own maester. If the maester was forced to write a letter claiming Stannis was dead, and Karstark was forced to sign it, and the letter arrived with the returning Manderlys, who carried Lightbringer and confirmed the story, would the Boltons be as skeptical? Especially as preoccupied and panicked as they are sure to be about "Arya's" escape and the failure to recapture her?

[Lord Varys]

The thing is:

Does it make sense after reading the gift chapter that Ramsay is not going to participate himself in the coming Battle of the Ice? That's what Theon assumes will happening.

You are right about the devastating effect the missing 'Arya' would have on the Northern army in Winterfell. That means they would have to hide the fact that she is gone from the common soldier/pro-Stark lords. Which means that the ruling cabal (Roose Bolton and Lady Dustin) will most likely order Ramsay to bring them back Stannis's head when they sent him out with the main host after the Freys and Boltons have gone.

Roose and Ramsay know that Jon Snow was behind Mance's infiltration to free 'Arya'. And the Pink Letter really indicates that the fear that Arya might actually arrive at the Wall. I really don't see why 1. we should believe Ramsay's claim that he has Lightbringer, nor do I believe Ramsay/Roose would believe anyone (most certainly not some Manderly knights) that Stannis is dead with only Lightbringer as proof.

The Karstark maester and his ravens could be used to deliver disinformation to Roose in Winterfell, but I'm not so sure that he would actually believe Stannis dead if only a letter told him that was the case, a knight of dubious loyalty delivered him a sword. Especially since Roose himself obviously used a letter containing lies to trick somebody else.

If Boltons soldiers/Ramsay would arrive after the battle and meet Manderly knights telling them that the evil usurper was dead, and his army slaughtered, they would insist on seeing the corpses (especially Stannis's corpse) for themselves. Even Ramsay is not stupid as this.

And I can't imagine Ramsay will return alive from the coming battle. If he fights, he will die. Afterwards, Stannis might try to lure Roose out by delivering truths and lies via the Karstark maester to Winterfell. But this might not be necessary. All Stannis has to do if he wins the battle is march to Winterfell, proclaim his victory, tell the North that he has 'Arya', tell them about Bran and Rickon and the Sacking of Winterfell (which he should find out from either the Manderly knights or Bran himself on the weirwood island), and the remaining Stark loyalists within the castle will open the gates.

But I'm not sure if Roose will not see that coming. My guess is that he will command Ramsay to write this letter, send him out to defeat Stannis, and then is going to abandon Winterfell and retreat to Dreadfort. Roose is way to cautious to risk everything, especially since he knows that he won't be able to save his skin if Stannis takes the castle. Roose looked scared to Theon back in ADwD when he last looked at him. He knows that if they did not get 'Arya' back, they are lost either way. Even if Stannis would be defeated, House Boltons would lose its claim to Winterfell. Nor idea why the North should stick to House Bolton afterwards.

[Jedi Master Hot Pie]

Robett Glover.

[Faint]

My guess is that he will command Ramsay to write this letter, send him out to defeat Stannis, and then is going to abandon Winterfell and retreat to Dreadfort. Roose is way to cautious to risk everything, especially since he knows that he won't be able to save his skin if Stannis takes the castle. Roose looked scared to Theon back in ADwD when he last looked at him. He knows that if they did not get 'Arya' back, they are lost either way. Even if Stannis would be defeated, House Boltons would lose its claim to Winterfell. Nor idea why the North should stick to House Bolton afterwards.

Explain exactly, in a way that makes sense, why the Boltons would ever assume that Theon is still alive and at the Wall?

Also, if they were going to lie to Jon anyway, why not just claim that they have Stannis' head? Why only mention that they have his sword?

So, let's get this straight:

Before Ramsay even left the castle to join up with the Manderly and Frey men, Roose instructed him to write a letter to Jon Snow, for reasons that are not entirely clear, and in that letter, Roose instructed Ramsay to say the following:

(1) To demand the return of 'Arya Stark' and Theon Greyjoy (despite the fact that they have no clear idea what happened to the two and whether they are even alive).

(2) To tell Jon Snow that they had defeated Stannis Baratheon and that they have his sword (but not his body).

And they're doing this to draw out Jon Snow to Winterfell even though Roose plans on fleeing to the Dreadfort.

Should I go on, or do you realize now that none of this makes any sense?

[Faint]

As to Lord Varys's point that Ramsay would seek confirmation of Stannis's death before acting, I think it's worth remembering that Stannis has captive Karstark, someone who the Bolton's believe is an ally, and the Dreadfort's own maester. If the maester was forced to write a letter claiming Stannis was dead, and Karstark was forced to sign it, and the letter arrived with the returning Manderlys, who carried Lightbringer and confirmed the story, would the Boltons be as skeptical? Especially as preoccupied and panicked as they are sure to be about "Arya's" escape and the failure to recapture her?

Exactly.

I'm convinced the letter was written under the following circumstances:

(1) Ramsay is back in the castle with Stannis' sword, having tortured Mance and Melisandre's plot out of one of the spearwives.

(2) Ramsay has been told by those returning from the battle that Stannis was defeated but Theon Greyjoy and 'Arya Stark' had been sent to the Wall beforehand.

(3) Ramsay sees a bunch of bodies (i.e., Freys with Stannis' banners) littering the battlefield but none of them are Stannis; there are also bodies inside the now open lake (it's even possible that the Manderly men and the Karstark men tell him that Stannis was one of those who drowned in the lake when the ice collapsed).

(4) The castle is getting restless, and the loyalty of the other Northern lords is growing increasingly questionable, especially since Ramsay and Roose don't have 'Arya Stark' anymore.

[Arkash]

Again, I've said this in the first page of this thread, but the image is so vivid in my head, I cant refrain myself for saying it again:

Ice lake trap !

I so want to read this with GRRM's writing, it can be visceral, and one of the best moments of the whole saga !

[thunder_chicken]

Again, I've said this in the first page of this thread, but the image is so vivid in my head, I cant refrain myself for saying it again:

Ice lake trap !

I so want to read this with GRRM's writing, it can be visceral, and one of the best moments of the whole saga !

Don't we know that Roose has a map of Stannis' encampment (and therefore where the lake is?) It will be interesting to see which of the three forces (Manderley, Frey, or Ramsey) did not get that information.

Also, one thing bothers me about the letter. Ramsey's absolute number one favorite thing in the world is hunting down escaped prisoners, something that he is apparently quite good at. To me this makes it unlikely he wrote the letter in some short window of time after the battle with Stannis, when he still thought he had the opportunity to track them.

[Free Northman]

The Freys will be slaughtered at the Battle of Ice. But most of Stannis's southern knights will die too, with minimal losses among the Northern Clansmen.

And something bad will happend to Stannis at this battle. I don't think he will truly die, but he will be removed from the game in some way.

However, the result of the battle will be kept a secret, with news coming back to Roose and Ramsay in some way that they actually won a victory.

As a result, Ramsay will write his letter, believing it to be true.

Winterfell will eventually be won by the loyalist northern forces using the secret passage into Winterfell alluded to in the final episodes of Season 2 of the TV series.

This is also what Mance's women were trying to question Theon about.

I don't think Stannis will enter Winterfell, but the loyalist (to the Starks) northern forces will take it.

Maybe with Rickon as their figurehead, or maybe with a resurrected Jon Stark leading them.

I can see Ramsay and Roose holing up in Winterfell until Jon or Rickon are ready to enter the scene, though. Stannis's victory at the Battle of Ice won't settle the matter of Winterfell until Jon or Rickon are ready to take it back. (Rickon as a figurehead for loyalist Manderly forces, but still, it will be northern loaylists as opposed to Stannis's forces that take Winterfell back.)

[TheeMikeHoncho]

quick questiton,

Since grrm states that tWoW takes off right from where aDwD ends and we know that Stannis is alive through theon's chapter, Isnt that proof that the letter is a lie?

[Arkash]

No, some events of Twow will take place earlier than some of Dance...

[Faint]

quick questiton,

Since grrm states that tWoW takes off right from where aDwD ends and we know that Stannis is alive through theon's chapter, Isnt that proof that the letter is a lie?

The letter, specifically, hasn't even been written as of end of the latest Theon chapter, whereas in the last Jon chapter in A Dance with Dragons, it has already been delivered.

[bemused]

I 'like" all these posts.. :D. I love a good brain wrestle...

Another possibility is :

We know Ramsay is sly and crafty, but not really a good tactician. Sure he cozened Theon when he held WF, but Theon was already desperate and unravelling somewhat at the time. Though Roose has repeatedly pointed out the folly in Ramsay's plans and suggestions, Ramsay doesn't really think father knows best , and he was just having a public argument with Roose ( that had Walda terrified ) right before they received the map of Stannis' whereabouts.

If , as Theon thinks, Ramsay will be deployed in mop-up position...and if he should receive word that the battle was well in hand , but that " Arya " and Theon had been sent on to the wall with only a slight lead... I think his lust for the hunt and his psycho-sexual sadism would kick in, and he'd be off after them . In his mind , it would be justified by the importance of "Arya" to the Bolton claim , but in his sick soul , he'd be slavering at the thought of having his favourite victims back in hand...Once started , I don't think he'd turn back even if it became apparent that their lead was considerably better than he thought. He'd just pillage as necessary on his way forward.

Roose has said Ramsay's passions would be his downfall , if he couldn't control them , and they may contribute to Roose's downfall as well.

Mind you , this would mean Ramsay probably didn't write the letter...

[Rockroi]

I was going to write a lengthy post but Varamyr Sixskins wrote a really really compelling argument that comports well with my own thought. I strongly suggest people read it. I believe a position very close to his, namely

I want to add a few points that may or may not add to his hypothesis.

1: Roose led the men out of Winterfell because he had to, not because he wanted to: One thing lost in this ruckus is what was happening inside Winterfell in the days and hours prior to Roose's march. Men were being terrorized by a secret killer; Manderlys and Freys were at each others throats complete with bloodshed and deaths. Winter had come to the North and there was no hope of resupply or escape. Men were not just getting restless but were becoming increasingly impotent as they could do nothing and fight nothing. And also, don't forget, these men were not actually experiencing Winter- they were snug, warm and being very well fed (Martin pay's great care in describing the tons of food they have). Now, this same army made up of disparate, waring parts marches out in the snow-filled expanse of the North searching for Stannis. These same men who were being well fed and protected from the elements are now thrust into the storm, with limited food and limited options and they are chasing Stannis.

This is not the army you want to be on the loose chasing after Stannis Baratheon in the snow in Winter. They 1) do not have the fortitude to stand up to this ordeal and 2) they do not have the unit cohesion to stand up to this challenge.

This says NOTHING about having to face Stannis.

2. Rush So Roose KNOWS he has to find Stannis and find him fast. His army is not equipped to march for 2 weeks in the snow and then do battle with Stannis- he has far too many men, far far far too many horses. Roose cannot feed all those men and horses not after the snow starts falling. So he has to find Stannis and Stannis is going to - very soon- WANT to be found. Historically speaking armies that rush out to do battle have met with disaster. The Spanish Armada was defeated because it was hastily rushed together and it was made up for disparate parts of the Spanish far-flung empire (also the ships apparently were made of new wood and gave off a putrid, noxious odor). The last German offensives of World War I and II were both thrown at the West and were defeated not just because they hit a well-organized and capable enemy but because they were no longer capable of supplying their army properly. It was either win or die.

Roose is doing the same thing- he is on the move against an unknown and unknowable enemy and he is rushing an unprepared, overly large army of disparate parts into a hostile environment. Roose does not have the supplies to feed this army nor does he have the ability to find his enemy. Roose's only valuable is this - the Karstarks. But we know the Karstarks have been caught (if Theon I is to be believed). Therefore Roose Bolton is rushing an unprepared, ill-fitting, hungry and soon-to-be disparate army made up of parts that hate each other into ... Stannis Baratheon.

3. Stannis the Mannis: The reverse side. Unlike Roose, Stannis' army has been bitchy with each other but they have NEVER come to blows; they are actually well fed, small and have commonality of purpose. They are also stationary and do not HAVE to move; they can wait. They are also remarkably well lead, well organized and perfectly situated.

And they have Stannis.

Stannis has a plan to use the terrain to his advantage against an all-or-nothing Roose et al. Stannis has the Karstark's neutralized and has taken their men. Therefore, Stannis has not only taken away men from Roose and augmented his own forces accordingly, Stannis has also taken away from Roose his "Ace in the Hole" and replaced it with a deuce.

Stannis also has the men galvanized. There is no signal from anywhere that Stannis' men are not coordinated properly or are sewing the seeds of rebellion. In fact, the Karstarks were taken so efficiently and so quickly that one must suspect that Stannis men are still running on better-than expected operating levels. Not only did he cut the head of the Karstark leadership but took all the men with virtually no difficulty. That's a far, far far cry from men butering each other in the Halls of Winterfell and then jumping on horses to get Stannis.

Stannis has a major difficulty but its manageable. Stannis biggest problem is the same now as it was after Blackwater- keep his movement moving, fighting and winning. That's that. IF the newest problem for Stannis is Roose Bolton, the PROBLEM is the same; only the head has changed.

Besides not needing to move, Stannis has the North's leading experts - Wull, Norey, etc -on the terrain, the weather, the local population, rivers etc. Stannis will not be caught with his britches down. By contrast, Roose's most capable men are all from the South of the Neck- the Freys; everyone else is potentially about to double-cross Bolton (Manderly and Dustin). This means that Roose has a ticking timebomb in his army and the only way to defuse it is to find Stannis and kill Stannis. And Stannis knows this.

Stannis is also a hardened, battle-tested soldier possibly the best battle-field talent left in Westeros. He's not going to bungle into Roose; he's going to make Roose come to him. In doing so, Stannis is acting to HIS strengths- Roose must rampage through unfamiliar terrain with an army filled with enemies and fight HIM on turf STANNIS chooses. So when Stannis and Roose meet it will be with Roose coming AT Stannis and not the other way around. With that Roose will fight Stannis on ground Stannis chooses, at a time Stannis chooses and in a way Stannis chooses. And Roose has no choice at all. He cannot dilly dally. He must stick with the attack; he must find Stannis and engage him in battle. And he must win.

With all that said, if you had to pick a winner in all that, who would you put your money on? Even if we throw in some odds, isn't it Stannis something like 4 to 1? 8 to 1?

But then we have the letter.

4. The Letter If we did not have the letter EVERYTHING would be in Stannis' favor. But the letter throws a wrench in that. The letter is almost entirely false (Martin has all but said that). BUt how false? And then how true?

For starters I do not think Ramsey left WF. I think he stayed. Therefore, he did not witness anything. Stannis pulled a big trick on him. Why? Because he cannot besiege Winterfell. He needs to force a battle. So if he can get Ramsey to open the gates- pull a Tywin to Ramsey's Aerys - then he wins the North- from the Wall to the Neck - for a song. Ramsey sending that letter shows that Ramsey - and I believe Ramsey sent the letter -is doomed. Ramsey thinks his men won, defeated Stannis and killed him. Ramsey, though, has a problem. He lost his bride and his reek (he says it like 4 times in the letter). Therefore, he can win a battle, but in RAMSEY's mind if Roose et al return in force and Ramsey is bride-less he's fucked.

But What Ramsey does not know is this: he just let Karstarks into his castle who are now loyal to Stannis; Manderly has crossed over and the bulk of the Frey legions are dead or captured.

THe letter represents a story that only exists if everything broke right for the Bolton forces and NOTHING has broken right for them. From "Arya's" escape to the Karstark capture to the flight from Winterfell its all been an absolute nightmare.

Its just that Bolton didn't know it until it was too late. And Ramsey does not know it at all.

When all is said and done, Stannis will have the following:

1. An absolute and total victory over Roose Bolton, crushing the FRey-Bolton forces, creating a vacuum in the North and cutting the life blood from the Freys in the South;

2. Access to Winterfell, the Seat of the North and the absolute control of everything from the Neck to the Wall;

3. Insulation. Nobody can invade the North now.

4. He has the Stark heir on his way to legitimize not only his armies but his claim to the Iron Throne.

5. A legion of soldiers who will not only follow Stannis, BUT are open to helping Stannis defend against what is beyond the Wall.

5. Literary Consideration: One last thing: if Stannis is still alive why? Why would Martin not kill Stannis along with Robb, Renly and the other "pretenders?" Other characters are killed once their is no more need for them- Tywin, Obyren Martel, Ned, Quentin, Robb- once a character outlives their usefulness, their death is eminent. Well, why is Stannis still here? So Roose Bolton can be Warden of the North? So Ramsey can be a crazy person?

Noooooo... THere is a reason to this and that reason is that Stannis Baratheon ... is a serious man. And as a serious man he has a purpose- he is going to fight the Others- AA or not. And to do that he needs the North.

And he's a bout to win it.

[Lord Varys]

Rockroi,

why do you think Roose Bolton would 1. lead the attack against Stannis personally, and 2. leave Ramsay in charge of the garrison of Winterfell?

All we know about Roose Bolton suggests the opposite thing. Roose is the most cautious man in the Seven Kingdoms. Yes, you are right, Stannis and the situation forced Roose to send his troops out to find and destroy him, at a place of his choosing. But why do you think he would accompany his troops?

In my mind the whole purpose of 'Ramsay Bolton' is to serve as Roose's enforcer. He is the guy Roose uses to do his dirty work, and that includes, to an extent, the leading of men into battle. If a quarter or more of the Dreadfort men would be sent against Stannis, Roose would send them out under the command of Ramsay and Steelshanks Walton. He would not go himself. He would rather rid the castle of most/all his potential enemies. If in the end only loyal Bolton men remained at Winterfell, Roose could fortify and hope to hold the castle successfully against Stannis, even if all his northern bannermen would abandon him (that is, as long as Stannis does not find a way to sneak in/open the gates).

But even if Roose for some reason would be leading his troops personally against Stannis, he would not die at the lake. He would remain in the rear, and retreat to Winterfell in time.

As I've already said, in my opinion it's much more likely that the Pink Letter has been written before the battle. And I think the Boltons are fucked even more. Not only is Stannis much more in control of the coming battle, he is also about to get 'divine help'. Bran and Bloodraven will interfere, I think, sending ravens and possibly even the trees against the Freys.

[7V3N]

I think Stannis will win because the Northern lords will join him.

But I certainly do not think this is the end of Roose Bolton by any means. Maybe he escapes through Winterfell's crypts or something? No way GRRM kills him off yet.

[Rockroi]

why do you think Roose Bolton would 1. lead the attack against Stannis personally, and 2. leave Ramsay in charge of the garrison of Winterfell?

In both cases he cannot trust anyone else to do it. HE certainly cannot trust Ramsey to lead an attack on Stannis and he certainly cannot stay at Winterfell while MAnderly, Frey or anyone else leads an attack to find Stannis. Roose is leading the attack because he HAS to; nobody else can.

In my mind the whole purpose of 'Ramsay Bolton' is to serve as Roose's enforcer. He is the guy Roose uses to do his dirty work, and that includes, to an extent, the leading of men into battle.

Oh I completely disagree- leading men and battle and doing diryy work are not the same thing at all. I think in the Reek chapter in ADwD when Roose talks to Reek at length about Ramsey it shows that Roose does not trust or like Ramsey. And he cannot- under ANY circumstances –trust Ramsey to lead troops in battle. Battle is not the type of “dirty” work that Roose has in mind for Ramsey, and Ramsey is NOT the type of person who can be trusted to lead men in battle and Roose knows that.

If a quarter or more of the Dreadfort men would be sent against Stannis, Roose would send them out under the command of Ramsay and Steelshanks Walton. He would not go himself. He would rather rid the castle of most/all his potential enemies. If in the end only loyal Bolton men remained at Winterfell, Roose could fortify and hope to hold the castle successfully against Stannis, even if all his northern bannermen would abandon him (that is, as long as Stannis does not find a way to sneak in/open the gates).

That ship has sailed. Roose cannot send ¼ of the WF troops out to find Stannis because, well, they may actually find Stannis- and get annihilated. That plan would also keep Roose at WF surrounded by Freys and MAnderly’s where BOTH would STILL be at each other’s throats It does not solve the problem. No half measure solves those problems. He cannot send out Ramsey with troops to fight Stannis because Ramsey would get butchered along with his men; he cannot send out other men because he does not trust them. No, Roose HAS to take all or he risks loosing it all. He must lead and leave Ramsey to hold the rear.

But even if Roose for some reason would be leading his troops personally against Stannis, he would not die at the lake. He would remain in the rear, and retreat to Winterfell in time.

For starters we do not know where Roose will be during this battle because Roose does not know when the battle will be joined. He could lead from the rear or the front. But also, if he does die in an ice-lake like battle, who is to say Ramsey knows he is even on the lake? And if he does NOT go on the lake, who is to say that Northern riders do not end up catching him?

Anything is possible because nothing has been ruled out yet.

[Lord Ben]

Personally I think the letter was written by Bran and delivered via Raven by himself in order to prod Jon to Winterfell and 1) Tip the scales towards Stannis. 2) There must always be a Stark in Winterfell and must is coming rather soon.

Maybe not but it's my crackpot theory.

[Lord Varys]

Rockroi,

I'm not sure if Roose does fear Stannis as much as you think he does. Tywin was bright enough to fear Stannis, perhaps because he knew firsthand what he pulled off before Fair Isle, but I'm not sure that Roose knows enough about Stannis to fear him (he has not watched 'Blackwater', after all ;-)).

Especially not since he still has reason to believe that Arnolf Karstark will betray Stannis. The Karstark betrayal would have broken the lines, and decided the battle before it even began. Even a fool like Ramsay could have done the rest. I'm not sure why Roose should change his mind on that. Especially since Ramsay most likely will be more than eager to march into battle to get his 'Arya' back (although I think the Boltons do indeed fear Theon and 'Arya' might be directly on their way to Castle Black, Ramsay would want to take his chance at Stannis's camp).

Roose showed fear in Theon's last chapter, but not so much because of Stannis, but because of the situation in Winterfell. His men were at each others throats. Sending out, even sacrificing the Freys, Manderlys, and other unsavory Northern troops, even Ramsay, might actually work to his advantage. He would be quite safe behind the walls of Winterfell, and would have more than enough food for himself and his garrison to outlast any siege conducted by Stannis.

I cannot see Roose taking a different approach. And the Pink Letter may be written in Ramsay's hand, but it was Roose's idea. Just as the letters to Asha and the first letter to Jon.

[Faint]

1. An absolute and total victory over Roose Bolton, crushing the FRey-Bolton forces, creating a vacuum in the North and cutting the life blood from the Freys in the South;

2. Access to Winterfell, the Seat of the North and the absolute control of everything from the Neck to the Wall;

3. Insulation. Nobody can invade the North now.

4. He has the Stark heir on his way to legitimize not only his armies but his claim to the Iron Throne.

5. A legion of soldiers who will not only follow Stannis, BUT are open to helping Stannis defend against what is beyond the Wall.

I question whether Stannis will actually be in such a cushy position following the defeat of the Boltons, even though, like you, I'm quite certain that he will indeed defeat them.

Various points to consider . . .

(1) With respect to the men he has right now, very few are his own men and even those grow less and less by the day.

(2) With respect to the men he has at the Wall, they find themselves smack dab in the middle of the chaos engulfing Castle Black in the midst of Jon Snow's assassination.

(3) Along with that, his men at Castle Black, including Melisandre and Selyse, last heard Stannis was defeated and slain. While they may soon receive contrary information, one wonders whether it will be soon enough, or whether his men there simply maraud beforehand (those that survive the possible conflict with the Wildings, anyhow).

(4) Justin Massey, who Stannis is counting on to acquire an army of mercenaries, is currently headed to Castle Black, where he might very well run into the savaged remainder of whatever is left of Stannis' men, along with the news that Stannis is dead and defeated.

(5) Manderly's support, and probably that of the other Northerns, is contingent on Davos retrieving Rickon. There is no telling when, even if Davos is successful, Stannis will know about it, or when Davos can make it to Winterfell.

In short, there are still a lot of questionable circumstances that would all have to break Stannis' way for him to secure the North even if he defeats the Boltons.

5. Literary Consideration: One last thing: if Stannis is still alive why?

So he can fall against Daenerys . . .

Glowing like sunset, a red sword was raised in the hand of a blue-eyed king who cast no shadow. A cloth dragon swayed on poles amidst a cheering crowd. From a smoking tower, a great stone beast took wing, breathing shadow fire. . . . mother of dragons, slayer of lies . . .

Martin, George R.R. (2003-01-01). A Clash of Kings: A Song of Ice and Fire: Book Two (p. 706). Bantam. Kindle Edition.