`Theon's Mistake

[Fear of Drowning]

A lot of people think Theon taking and trying to hold Winterfell was a bad move. I disagree and think it was a great idea. Theon's mistake was expecting Asha to put the interests of her people and the overall success of Balons war before her own prestige and desire to succeed her father. IMO emotonal Stark nationalism also often clouds peoples assessment of Theons actions.

In A clash of Kings Asha tells Theon (CoK 56):

“You might have thought of that before you took it. Oh, it was cleverly done, I’ll grant you. If only you’d had the good sense to raze the castle and carry the two little princelings back to Pyke as hostages, you might have won the war in a stroke.”
...

“Your prize will be the doom of you. Krakens rise from the sea, Theon, or did you forget that during your years among the wolves? Our strength is in our longships. My wooden pisspot sits close enough to the sea for supplies and fresh men to reach me whenever they are needful. But Winterfell is hundreds of leagues inland, ringed by woods, hills, and hostile holdfasts and castles. And every man in a thousand leagues is your enemy now..."

We have the claim that holding Winterfell is a bad move from Asha's lips, but to my knowledge from no-where else. On the surface this sounds plausible and Asha is a likeable character. However, she is Ironborn, her fathers daughter and a player to boot. If Theon were to successfully take and hold Winterfell, Asha has no chance of being Balon's heir. It is in her interest to see Theon fail. I name her words here self serving lies.

Holding Winterfell is a realistic proposal with a relatively small number of men. Maester Lewin (CoK 66) tells Theon:

“If you had a hundred archers as good as yourself, you might have a chance to hold the castle”

Given 300 seasoned Ironborn, a mixture of archers and melee troops the odds would be in Theons favour. With 500 he could hold Winterfell comfortably.

500 men is a tiny part of the Ironborn strength. Of the estimates I have seen on these forums for the Ironborn total strength 12'000 is the lower end. Removing 500 to hold Winterfell does not seriously dent these numbers, and Winterfell is worth holding. Winterfell is a symbol. The Ironborn holding Winterfell is a massive blow to northern morale and the prestige of House Stark. It was Theon's taking of Winterfell that convinced Roose Bolton to betray Robb Stark. If the Ironborn are to be successful in their war they need the north divided and demoralized. By taking and holding Winterfell the Ironborn show their cunning and prove that they are more than primitive, opportunistic sea raiders, they deal a crushing defeat to House Stark on its own terms. It is a good idea for precisely the reasons Asha claims it is a bad one. It is likely to lead to some opportunistic Northern Houses switching sides, weakening the enemy while bolstering the Ironborn forces.

Should the Ironborn garrison winterfell with ~500 men, they tie up many times that number should the Northern Lords attempt a siege. It makes a pincer movement attack on Moat Cailin from the north as well as the south much more difficult, or perhaps even impossible.

So Theon needed men to hold Winterfell. He was IMO foolish to put all his eggs in one basket and expect them from Asha. Indeed he should have realized that she would want to see him fail. Where else could he get them?

1. Most obviously there is his own command. He is given 8 longships which ac old ~80 men. That's ~640 men. He allows himself to be intimidated by Aerion and leaves the bulk of his forces (6 ships) with his uncle. Of the 160 that remain to him he sends the bulk with Dagmer in his feint against Torrhens Square. A bolder man that Theon would have arranged an accident for Aerion and taken his entire command. As it is, Theon did not push very hard for the men he needs - for a 50/50 split or to leave Aerion with 2 ships and take 6. The Ironborn may have faith in their god which they don't have in Theon, however they are not ascetic like Aerion is. They are greedy for plunder and glory. By leveraging this, promising the men the moon and also by being less squeamish (i.e. Drown Tallhart himself) Theon could IMO easily have taken more men than he did.

Further, he could have given Dagmer orders to disengage and make his way to Winterfell. There is a chance Dagmer would disobey, wanting glory of his own, however this is definitely worth a shot, Theon should have tried every avenue open to him to get men to Winterfell.

2. Victarion at Moat Cailin. Victarion has not proved himself a rival the way Asha did when she humiliated Theon. He is a dutiful warrior and IMO a much better bet. Of course he didn't assist Theon when Theon was already in trouble and under siege, begging for help and offering nothing. Things may well have been different if Theon had offered something in return and asked earlier from a position of strength rather than desperation. Theon did not expect to find the Reeds at Winterfell, but he did expect plunder, the Winterfell silver and Bran/Rickon.

IMO the sensible move would have been to dispatch 5 men on winterfell horses to Moat Cailin with Rickon, the Reeds, the Winterfell silver and any other valuables that are easily carried as soon as he took the castle (with a larger force because he didn't let Aerion cow him). Bran stays to cement the hold on Winterfell. Moat Cailin is next to the sea, the silver and Rickon are to be delivered to the Iron Islands, the silver used to raise men to replace the ones at Moat Cailin sent to Winterfell. The Reeds as hostages would help Victarion immesurably. Were Theon after men from Moat Cailin from the get go he would have realised this and made use of them. Possibly Theon goes to Moat Cailin to make his case. If not he gives his representatives a detailed description of why holding Winterfell will benefit the Ironborn war effort in general and Victarion mission at Moat Cailin in particular.

If Victarion refuses, some of the silver and the promise of richer plunder may be used to induce some of his men to head to Winterfell anyway. House Codd I'm looking at you.

3. Asha. If it is clear Theon will be getting men from elsewhere Asha may well reinforce him as well, to avoid looking like a traitor. Send the same detailed letter about the benefits of holding Winterfell, ensure it is read before her men. Worth a shot.

Theon, of course, also didn't have any contingency plans - which was silly in such a high risk endeavor. He would never be capable of burning Winterfell and retreating because that would mean killing everyone he had grown up with. He should have realized this and planned for it. Thus going to Moat Cailin himself and naming a castellan may have been the best option.

- - -

TLDR: Theon taking Winterfell was a stroke of Genius. Holding it was a good idea. What was stupid was expecting Asha to help him upstage her by providing reinforcements. From the get-go he should have been looking for reinforcements from elsewhere.

[aryagonnakill#2]

Gotta disagree, Asha had the right of it. The best move Theon could have made was sacking the castle and taking Bran and Rickon back to Pyke and presenting his father with a Direwolf coat. Robb would have granted them any consessions they wanted.

[Tynned Lannistark]

I think Asha was very right in her words to Theon. I think it was a solid advice and not sure at all it was driven by her own ambition.

Taking Winterfell was a brilliant move - Theon proved skill, cunning, courage and most importantly that he was not loyal to the Starks.

It had a devastating effect on the Starks as you mentioned - casuing Roose to switch sides, eventually killing Robb and denying the Northreners any possibility for retribution which was a real risk in Balon foolish and uncareful plan. Theon may have just saved their asses big time and if it wasn't for Stannis, IB would still rule some of the north.

The iron born are raiders. They do not have the power to rule a land like the north. The only way they could have conquered any additional land is what Asha suggested in the kingsmoot.

There is no gain for Theon in Winterfell. Only troubles. Had he razed winterfell and went back to Pyke with the captive princes and plunder he would be a huge hero and made a huge step towards becoming Balon's heir.

But Theon is an arrogant fool who thinks like the people he grew up with, not like an IB, which is why he keeps Winterfell and inevitably fails.

[Fear of Drowning]

Obviously Theon would have been in a better position had he kept Bran and Rickon as hostages rather than letting them escape. However this is separate to the question of whether or not to hold Winterfell. I agree the best move would be to send one of them back to Pyke as a gift to Balon. Separated there is less chance of losing them both.

I don't think King Robb would have given Balon whatever he wanted just because Balon held Bran and Rickon. Balon wants the entire North or as much as he can get. Bran and Rickon are valuable bargaining chips, however their worth is not unlimited. If Robb offers his entire kingdom and sells out all his bannermen in exchange for them his bannermen rebel and this nullifies the deal. Winterfell is also a valuable bargaining chip. You get a better deal offering Bran, Rickon and Winterfell back than you would just offering Bran and Rickon.

You look stronger and Robb looks weaker if you take and hold Winterfell, than if you take Winterfell, burn it and run away. There is also the fact that Theon is not emotionally capable of burning Winterfell. That means killing everyone there, everyone he grew up with. Theon is not capable of this.

The Ironborn are Raiders, but they are more than just Raiders. Once they were conquerors. Before Aegons conquest they held the Riverlands.

[Nerevanin]

I think it was clever of Theon to capture Winterfell, he proved that he is clever and brave and surely he wanted to impress his father. His mistake was thinking that he could hold it and rule. He should just take the loot, Bran, Rickon, maybe someone else as hostages and leave. If he wanted to do some damage to Starks (to Robb) - which I doubt, I think his only reason was to impress his father - he could keep the castle until Robb turns to the North or something, which would give time to Lannisters to recover a bit, and then flee.

[Victor227]

I think Asha's perspective was based around the fact that she thought the conquest of the North was a stupid and impossible idea from the get-go. She doesn't believe the Ironborn can hold the North, let alone rule it successfully, so to her Winterfell has absolutely no value whatsoever.

Her suggestion about taking Bran and Rickon as hostages and razing the castle in his wake shows she believes the war to be a ephemeral thing that can be 'won' through means other than total conquest. The double-blow of losing his heirs and having to rebuild his castle would certainly force Robb Stark to the table and burn away his prestige, but he'd never hand over the North for his siblings, not to the Ironborn.

Asha wanted land and concessions, she didn't want the North, and likely never thought conquering it was a realistic prospect.

[Fear of Drowning]

Why couldn't he hold it though?

Of course he couldn't hold it with ~20 men. However he was only in that situation because he expected Asha to reinforce him and she didn't. If he had taken steps to ensure he had a few hundred men he could have held the castle. Maester Lewin implied as much. Theon had many more motivations than impressing his father. Being Prince of Winterfell is what he dreamed of all his adult life. In Dance he pretty much says all he ever wanted was to be a Stark. Conquering and ruling Winterfell is the next best thing. He envied Robb/Bran/Rickon and wanted what they had.

Asha's concessions were to come in exchange for handing back Deepwood Motte and Moat Cailin. Following this route, more concessions could be gained handing back Deepwood Motte, Moat Cailin +and Winterfell+

[Tynned Lannistark]

Why couldn't he hold it though?

Of course he couldn't hold it with ~20 men. However he was only in that situation because he expected Asha to reinforce him and she didn't. If he had taken steps to ensure he had a few hundred men he could have held the castle. Maester Lewin implied as much. Theon had many more motivations than impressing his father. Being Prince of Winterfell is what he dreamed of all his adult life. In Dance he pretty much says all he ever wanted was to be a Stark. Conquering and ruling Winterfell is the next best thing. He envied Robb/Bran/Rickon and wanted what they had.

Asha's concessions were to come in exchange for handing back Deepwood Motte and Moat Cailin. Following this route, more concessions could be gained handing back Deepwood Motte, Moat Cailin +and Winterfell+

Exactly like Asha told him, the IB strength is in their longships. On land, surrounded by enemies he has little chance to survive. Even if he had more men he is surrounded by enemies who hate him and want him dead and even if he survives, what good is being a prince of a kingdom that is in the size of one castle?

His goal is to win back his position among the IB. They respect raiders, not castle owners. The guy just proved himself the top raider in the gang. All he has to do is go home and enjoy the fruits of his actions.

But exactly like you say , he doesnt want to. He can't bring himself to burn Winterfell. he wants to rule it. In his heart he is not IB, he thinks like the Starks and wants to be like the Starks. This is where he fails.

[Fear of Drowning]

Exactly like Asha told him, the IB strength is in their longships. On land, surrounded by enemies he has little chance to survive. Even if he had more men he is surrounded by enemies who hate him and want him dead and even if he survives, what good is being a prince of a kingdom that is in the size of one castle?

His goal is to win back his position among the IB. They respect raiders, not castle owners. The guy just proved himself the top raider in the gang. All he has to do is go home and enjoy the fruits of his actions.

But exactly like you say , he doesnt want to. He can't bring himself to burn Winterfell. he wants to rule it. In his heart he is not IB, he thinks like the Starks and wants to be like the Starks. This is where he fails.

Harrenhal

If the Ironborn do not respect castle owners why did they pick the Greyjoys of Pyke as their overlords? What is Pyke? Holding castles is a huge part of their history and traditional way of war. Doing this is not 'thinking like the Starks'.

Theons goal is to win victories, harm the enemy and generally make an effective contribution to the war. Winning prestige is a secondary effect of this. Why would he have 'little chance to survive'? Being surrounded by enemies who hate you means you are fighting a war. To effectively fight a war you face your enemies, you don't run away and 'enjoy fruits'. By holding Winterfell rather than running like a craven he ties up massive numbers of northmen and continues/extends the humiliation of House Stark.

If he survives he has taken the seat of House Stark, humiliated his enemy far more than he would have by burning and running, tied up their men and probably killed loads of them if they tried to storm Winterfell. He has effectively prosecuted the war.

[Slender Aimry Hill]

I find this pretty convincing - especially your point about Victarion and the Reeds, an astute bit of diplomacy which contrasts amusingly with Theon's actual reaction: 'ugh, mudmen. The girl isn't even that attractive and what in Westeros are they doing here'

I think Asha isn't clearly a consistently written character (slavishly pro-Balon ACoK, apparently a secret peacenik pragmatist AFFC, but supposed to also be a straight-talking non-hypocrite); by pointing out her deviousness and fallibility you thus also make a bit more sense of her motivation; well done.

I do like, however, to ponder on the what-if of Theon following her advice (I've always been amused by the thought it might have led him to being matched with Cersei).

[Fear of Drowning]

I don't find Asha inconsistent, just a devious and astute player. In order to get the +good+ peace she argues for in the kingsmoot the Ironborn have to negotiate from a position of strength. In order to get to that position of strength they need to take Deepwood Motte and Moat Cailin. The Glovers are willing to offer the Ironborn the land Asha wants in exchange for getting Deepwood Motte back. If she didn't take Deepwood Motte she would have nothing to offer at the bargaining table.

She clearly knows how to play Balon like a fiddle and massage his pride. Her humiliation of Theon clearly shows her selfish cunning and manipulative skill. In her POV's she makes clear that she hated Balon and often fantasized about killing him. She is just a great player and a great actress.

[BRANDON GREYSTARK]

Thinking that he was still Iron Born .

[Fear of Drowning]

Thinking that he was still Iron Born .

Euron isn't particularly Ironborn, as Aeron and Asha endlessly point out. He seems to do OK...

[devilish]

Asha was right. The iron islands had no chance in hell to beat the North head on. It simply had too many human resources. What they could do was hit and run.

[Steelborn]

Thinking that he was still Iron Born .

I have to agree. And this sums up the post I was about to send.

[Fear of Drowning]

Asha was right. The iron islands had no chance in hell to beat the North head on. It simply had too many human resources. What they could do was hit and run.

But that isn't what Asha (or Victarion) does. Her objective is to take and hold Deepwood Motte (Victarions to take and hold Moat Cailin).

[devilish]

Theon biggest mistake was betraying Robb. He simply underestimated himself for what he was ie Balon's only son who was raised by Ned Stark an honorable man. Having someone who valued honor and loyalty ruling the iron islands was every king's interest. No one wants mere pirates sitting close to his kingdom.

[devilish]

But that isn't what Asha (or Victarion) does. Her objective is to take and hold Deepwood Motte (Victarions to take and hold Moat Cailin).

They are both close to the sea. If things do get messy they can flee.

[Maid So Fair]

Even if he manages to hold the castle, it will have but symbolic value as it's put to to siege/stormed soon after. There would be absolutely no strategic benefit to the Ironborn because Winterfell, as Asha says, is way too far from their supply lines to use it as a stronghold to retreat to in an emergency or as a base for further conquest. Any Ironborn army seeking to even move to residence would be decimated en route (and it would take a lot more than a couple of hundred men to move past all the other lands to actually get to Winterfell in one piece). The only reason Theon succeeded was because he took a small force, created a distraction, and moved swiftly and under cover. A force openly seeking to cross half the North would be a sitting/riding duck for every northern soldier in the vicinity to ambush. Lady Dustin might not (claim to) like the Starks, but she's not letting an Ironborn army march through her lands unopposed.

[Steelborn]

Theon biggest mistake was betraying Robb. He simply underestimated himself for what he was ie Balon's only son who was raised by Ned Stark an honorable man. Having someone who valued honor and loyalty ruling the iron islands was every king's interest. No one wants mere pirates sitting close to his kingdom.

Who's this king? And why would the Iron Islands accept it just because a king of another place likes it?