In the latest installment of the second-best podcast about ASOIAF, Jeff Hartline talked about a parallel between Robb Stark's attack on Oxcross and two historical battles: Alexander the Great's use of a goat path to conquer the fortress of Tyros and Hannibal's sneaking into Italy by way of the Alps. The historical analogy is interesting, of course, and being a historian by profession, my mind immediately added one more: the German attack on France in 1940 through the Ardennes. While different in scope, I think it tells us more than Alexander's victory, other than Alexander inspiring the (of course great) literary trope of the goat path. The Germans and Hannibal didn't exactly use goat paths.
But I think the parallel is interesting for other reasons. The French, Sempronius Longus and Stafford Lannister all got a lot of flak for not being prepared for the result of this, but I think in part at least it's unfair. Yes, Stafford Lannister should've posted sentries, if only to make a habit out of it, but given how the Blackfish neutralized Jaime's outriders, I somehow doubt the sentries would've made much of a difference.
What the historical analogies show us is something different. The German attack through the Ardennes and the following encirclement of the Allied Forces (operation sickle cut, or, in its native German, Operation Sichelschnitt), Hannibal's crossing of the Alps and Robb's sneaking around the Golden Tooth all have something in common. They succeeded.
Duh, you might reply. Of course they did! They were brillant examples of maneuvering! Yes, of course, but they were also insanely risky. There's a reason these attacks achieved surprise and came totally unexpected. And that reason is that they really shouldn't work and could lead to utter disaster in a hurry. Let's have a look at the historical examples first before we check in on poor sod Stafford.
Let's start off with Hannibal. The route through the Alps was very treacherous and difficult and couldn't really be traversed with an army, let alone one containing elephants. Appropriately, Hannibal suffered high losses. It's unclear as to how high exactly; the Romans, never shy, attribute the number to 20.000 (roughly half his forces), but that's just insane propaganda. Much more likely are the lowest estimation of 500 to around 2000, cited by Delbrück. That means that Hannibal lost something between 2.5% and 10% of his troops crossing the Alps; famously, all but one elephant also died (a fact the Romans later left out to make him more scary). The army descending into Italy wasn't in very good order, exhausted and without any natural supply lines.
Now, had the Romans assessed the situation quickly or even gotten word in time, they could have blocked Hannibal there and then with their legions and obliterated him. Especially in the 3rd an 4th century AD, this problem would plague many would-be conquerors of Italy. Mountain passes usually only have one exit, so if you block it, the enemy army is trapped.
But, Hannibal got lucky. He then got lucky once again, as his opponent Sempronius let himself be encircled with 42.000 men, of which maybe 10.000 made it out of that trap alive. Well, not one for despairing, the Senate send the next army, which was obliterated at Trasime, to be followed by the infamous disaster of Cannae. That's three disasters that could've been avoided had Hannibal been a less brillant commander, his opponents a bit less daft and the luck not so decidedly with him.
Fabius, the famous "Cunctator" (translating roughly to "waverer"), recognized all this, refused to give Hannibal battle, played the logistics game and defeated him. Or rather he would've, if the Romans hadn't gotten fed up by being showed what jackasses they were and nominate different guys that then picked up the strategy.
Anyway, long story short, Hannibal's chances of being completely defeated by his trick were at least as large than the chance that he'd defeat Rome. As he soon learned, he had no supply train and no siege equipment. So while he could mount the biggest chevauchee of the period, he couldn't actually conquer Rome. And thus, he perished.
Wind forward 2300 years. The French and British armies were very confident in 1939/40 that they could defeat the Wehrmacht, since the Wehrmacht was under-equipped and couldn't hope to punch through Belgium and the North of France towards the Marne. Assaulting the fortifications of the Maginot Line was also out of the question, and the German economy was in such a bad shape that they'd lose the war in 1941 by sheer lack of ammunition. So, the Germans went for a rather drastic gamble, their hand forced after the initial plan of attack (which was the conservative one the Allies expected) fell into Allied hands because a staff officer mistakenly landed his plans on a Belgian airport and got arrested before realizing his mistake. Funny how history sometimes plays out.
The new plan had been discussed in the General Staff before but dismissed as way too risky, but Hitler, always one for betting everything on one result - a trait he shares with Hannibal and Alexander both - decided to go for broke. The German tank force would force its way through the Ardennes, a hilly and wooded terrain with very few passable roads (three, in fact), coming out behind the Allies and cutting through to the Canal coast - all with basically the supplies they had strapped on or could pillage. It was insane.
The length of the columns alone would have stretched from the Ardennes to the border with the Soviet Union if taken together, and if only one Allied plane had seen them, they could have blocked the passages with basically three AT guns and created the longest traffic jam in history, to be bombed at their leisure while driving their forces into the Ruhr.
However, while the traffic jam still occurred, the plane didn't materialize, and so the German tank forces emerged in the Allied backs. Even then, they could've been stopped with some decisive action, but the command structure was too slow and the commanders too inflexible to realize what was going on until it was too late, only to completely panic then.
The Germans also benefited from a few commanders, Rommel and Guderian most famous among them, simply ignoring orders and driving their battalions like hell without any contact to their troops or supply lines. One engagement at the wrong moment, and they're toast, the whole German line, fractured as it already was, breaks completely. In the event, that didn't happen (save for one isolated incident at Arras that clearly shows the insane danger they were in) and the guys became celebrities, but later in Africa and the Soviet Union, they would lose men and equipment in spades because this approach didn't work out.
Long story short, if not for a chain of factors that all needed to happen the way they needed, Germany would have lost the war by losing its tank force in the Ardennes and then the rest in short order in the summer of 1940.
And that takes us to Stafford Lannister and why we shouldn't be too hard on him. After all, sneaking past a complete army on horseback on a goat path is not what any serious commander should base their strategy on. If Robb Stark had been sighted, he could've been completely cut off. Even if he made it into the Westerlands, had the Lannisters been alarmed, all castles would have been manned, the cattle and treasure secured and the cavalry army without any siege equipment could have uselessly roamed around.
Robb's move, in the event, worked, but it worked because his enemy did EVERYTHING he needed them to do (much like Hannibal and Hitler, sorry for lumping Robb into that category). If the enemy is only moderately competent, if the commanders on the ground aren't at the absolute top of their game and taking insane risks on the spot, the whole thing falters. And operations such as these falter a lot more than they succeed and lead to immediate disaster, which is why usually, people prefer cautious and boring tactics.