Balon Greyjoy's military strategy, and why it's so retarded:
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Let’s set to one side that Balon, whose main political objective is the independence of the Iron Islands from the Iron Throne, decides to attack the one combatant in the War of Five Kings who is also fighting for independence from the Iron Throne and who wants to ally with him. Even if you take the point of view of an Ironborn who wants to conquer the North, this is a shoddily-designed plan. Note that Balon’s plan envisions a distracting attack at the Stony Shore, a small assault aimed at Deepwood Motte, and a main attack at Moat Cailin – and that’s it, no attack on Torrhen’s Square, no attack on Winterfell itself. The entirety of the interior is left untouched.

Balon assumes that Winterfell will fall, but his plan gives him no way to actually project force the 590 miles from Moat Cailin to Winterfell, or the 300 miles from Deepwood Motte to Moat Cailin, let alone the hundreds and hundreds and hundreds of miles he’d need to actually make the interior “ours, forest and field and hall,” as he intends. Not only is this poor logistic planning, but the assumption falls down on the first hurdle. We know from ADWD that Deepwood Motte is right next to three thousand hill clansmen who hate the Ironborn, and that there are thousands of Northern soldiers in the central interior who can be mobilized even if they weren’t distracted by the Hornwood affair, and thousands more in the eastern half of the North which Balon has no way of actually attacking.

But even if none of that were true, it’s still poorly designed from an amphibious invasion perspective. In the northern sector, Bear Island is the superior landing zone. To begin with, it’s an island that’s separated from the mainland (an island that the Ironborn were historically able to actually control for extended periods of time), which would allow the Ironborn to attack an isolated House Mormont, and then establish a forward base that can’t be attacked by the landbound Northmen, giving Asha a naval base from which she can dominate the whole of the Northwest, while still maintaining the operational flexibility to reinforce other areas as needed. In the south, while taking Moat Cailin is critical for ensuring that Robb Stark can’t easily fight his way back North, Balon neglects the opportunity to use the riverrine approaches that would lead the Ironborn straight to Barrowton or Torrhen’s Square, which would offer him a forward base in the interior, a short march away from Winterfell with clear lines of supply and reinforcement. Likewise, Balon makes no provision for transshipping the Iron Fleet from Moat Cailin to the Bite, which would allow Victarion to attack White Harbor, Ramsgate, the Dreadfort, Last Hearth, and Karhold, again using riverrine approaches to preserve the Ironborn’s lone strategic advantage.

Instead, Balon pushes the “hard heart of the Greyjoy strength” to Moat Cailin and leaves them there, hoping that the Lannisters will do his fighting for him. But he doesn’t do anything with this strength – in the seven months between the initial attack and Balon’s death, the Iron Fleet doesn’t move from Moat Cailin. Given that the Moat can easily be held against an army from the south by a few hundred men, this is an insane waste of time and manpower that could have been put to better use actually conquering the North instead of grabbing two castles and thinking that means the war is won. Consider what would have happened if the North had put Moat Cailin under siege from the North, especially if they’d been able to cut Victarion off from his boats? Balon’s main strength would have been cut off, starving, diseased, and poisoned, withering on the vine.

As this suggests, Balon’s plan is almost deliberately ignorant of the realities of Ironborn manpower. When Theon arrived at Pyke, he found “fifty or sixty longships,” and Dagmer sent to “roust the Stonehouses and the Drumms,” and in this chapter, “Lord Goodbrother of Great Wyk had come in the night before with his main strength, near forty longships.” 90-100 longships, carrying 30 men each, works out to 2,700 to 3,000 men. Add on to this the 100 larger ships of the Iron Fleet, which can hold 100 each, adding up to the “hard heart” of 10,000 men. That’s it; 13,000 men to defeat and hold the whole of the North. And as I said, Theon is sent with eight ships (approximately 240 men) and Asha with thirty ships (900 men), and everything else, around 12,000 men, is completely wasted at Moat Cailin.

The Ironborn simply do not have the numbers to take the whole of the North. The North is between 900,000 and 1.5 million square miles, so that the Ironborn would have one soldier per 69-115 square miles to try to occupy the whole of the country. Moreover, to really hold the country, the Ironborn would have to batter their way into at least 12 castles (that we know of) and all the defensive multipliers they offer, and then garrison them. All of this on lines of supply and communication stretching 2,000 miles. And winter is coming.

The only thing that can explain this complete irrationality is, once again, the inherent racism built into the Iron Island’s warrior culture. To Balon, the North is full of “cravens, old men, and green boys,” fit only for being “thralls and salt wives,” its lands existing only as a lebensraum to be conquered rather than to be comprehended as the strategic and logistical challenge they are. To know better is to remember the shameful defeats of Ironborn history – Theon the Hungry Wolf, King Rodrik; Rodwell, Beron, and all the other Starks who refused to give in to Dagon Greyjoy; and Eddard Stark, who brought the fury of the North down on Pyke. And Balon refuses to remember anything but the victories of the past.

The bottom line is this: Balon’s plan never should have worked.