Pobeb's theory is the best I've seen about the Pink Letter. Let me add a few things: * The pink letter says that all of Stannis' army was smashed. Stannis had much more knowledge about the events than Bolton. Bolton got a map with Stannis' camp, but he knows that and will adapt accordingly. Stannis knows the Karstarks were supposed to betray him and disabled them. He also knows that the Freys and Manderlys are coming. While per total, Bolton's army is greater, it's safe to assume the Frey + Manderly army is about half of that ... let's say a total of 3,000 ? Do we actually have numbers about Stannis? Remember that hundreds (I will use 1,000) from his army was supposed to turn cloak - so the Frey + Manderly + Karstark army would be let's say 4,000, while assuming Stannis had 5,000 initial - he would be left with 4,000. So how would the Frey army *smash* Stannis? Even from the Bolton perspective, it would be an even fight, with them having the element of surprise (the karstarks) + having information about how they were deployed, but relatively equal numbers. So "Ramsey following" would be to "finish off" the few survivors, in case Stannis won. But I think he never intended to follow. Why would he? Winterfall was full - so sending the Freys and Manderlys would result in: less overcrowding, less trouble, less of Stannis after the fighting. Why then risk and get out when the weather is so bad? They can just wait them out. Roose knows he's safe in Winterfell, and Ramsay is no fool. Thus, I think Ramsey never indented to follow in battle. * From the above + the sample chapter I think it clear that: 1. Stannis easily wins the battle, especially since the Manderlys will attack second, so the Freys are virtually surrounded. If indeed he will use the lake, then he will probably have virtually no casualties. If there will be a battle, there will be a Frey massacre, with probably tens of casualties for the combined Manderly + Stannis armies. 2. Even with no casualties, and the addition of Manderly - 5,000 - 1,000 karstarks + 1,500 manderly = 5,500 vs almost 4,000 (>6,000 - 3,000) - there is NO chance he can take Winterfell. So obviously, there must be trickery involved! It's clear that Tybald's ravens go to Winterfell, and Stannis kept them with intent to use them. How else but to send fake messages to the Boltons? Now, Ramsay said the battle was 7 days. This means the letter was sent at least 10 days after the Frey/Manderly army was dispatched. 3 days road + 7 days battle + raven. If he indeed has heads on the wall, and Lightbringer, this means that the letter was sent at least 13 days after: 3 days road + 7 days battle + 3 days road back. Another possibility is that Stannis won the battle, then attacked Winterfell and lost. This is very unlikely: 1. this places the events way further on timeline: 3 days road + battle 1-2 days at least + recovery and raise camp 1-2 days + 3 days road to winterfell + 7 days battle at winterfell = around 17 days - by that time fArya would have arrived at Castle Black; 2. He says he has Lightbringer, and his mens heads, but not Stannis's head. How would he have Lightbringer but not Stannis's head? So either he doesn't have Lightbringer (but was fed the information it was captured), or indeed he has the sword, from the Manderlys that came back - as a ruse to have the doors opened. 3. Stannis would have either Theon with him, or have him already executed - in both cases Ramsay would have known Reek's fate. He is looking for Reek at the wall, so this must be more fake information he was fed. 4. GRRM said there will be 2 fights. One it's in Mereen, we've seen chapters. Second must be The Battle by the Lake . I think he would have mentioned a third battle (of Winterfell) if that was the case. The clues point to Stannis faking his death (from the discussion with Justin Massey) to trick the Boltons. Also, I find it very likely that the Boltons have Lightbringer as part of that ruse. Here's how I think things went down: 1. Freys attack. Very possible they are on that lake - it's the obvious "natural defence" Stannis can make use of. Manderly attacks them from behind. Very few losses for Manderly + Stannis. 2. Theon is taken to the tree to be beheaded. I think it's clear to Asha that Theon is a broken man - both mentally and physically. She cannot use him for the kingsmoot, nobody would follow him. He is clearly in a lot of pain. And Stannis was clear that he will be executed, that nothing could save him. She is a prisoner herself, more or less. So either he will die in pain from his wounds/treatment (being hung 6 feet up) wwaiting execution, or he will be burnt alive. It's even possible Stannis intends to burn him alive before the fight, a sacrifice to have the red god on their side in the fight. (So then move this before the above.) Knowing this, Asha insists on the beheading, to save him the suffering. We've seen through Theon how Asha looks at him, clearly she just want him put out of his misery. 2'. At the tree, don't expect super display of Bran magic. There would be probably a few words heard, either from the tree or from the crows, words which would make Theon confess about the miller boys. (if the execution is before the fight, this will be enough for Stannis to postpone the execution to get more information). Theon is no kinslayer, but still turncloack. Maybe he's got even more information. Execution postponed. More input data required. 3. Surprisingly (for Stannis), Manderly killed the Freys. Discussion ensues. Wyman tells a wild story about Davos being sent to fetch Rickon from Skagos. No, it was not his head. Oh, you think my idea of deception with fake head on a spike was cool? Yes, I will let you use it against the Boltons too. Stannis also verifies from 2 sources that Rickon is alive. This means Theon was right, which means Bran might be alive too. His problems with who inherits Winterfell are also over. Northmen will fight more vigorously now knowing Starks are about. Maybe even Davos and Rickon show up for further motivation (unlikely... but not VERY unlikely - Davos + Osha + Rickon can travel quick: Osha has experience with travelling fast in snow, she knows what a warg is and maybe figures out Rickon is one, and then Shaggydog is used for reconnaissance and Shaggydog finds Stannis's camp) 4. Planning ensues for a few days. Camp is going to be left behind. Karstark sends raven message that battle was won. Manderly messenger is send ahead with news of victory, Lightbringer, and a few heads. Maybe even a few of some of Stannis's knights that died in battle. A few Stannis men dress up as Freys. The remains of Manderly + Frey army will be a few days behind, after tending the wounded. 5. Messenger arrives full of lies/sword/heads. Ramsay sends the Pink Letter. 6. Couple of days later, Frey + Manderly soldiers are at the gate. Gate opens. Boltons are game over. I don't even think there will be a fight, since Stannis will have opened doors and more men, and the element of surprise. Like said previously by many: Stannis is thankful to Jon for his letter, he would never send a fake letter. By GRRM, timing of the letter is after the battle. And Asha - what would she gain by having a few Nights Watch men coming to attack Stannis in Winterfell after 2-3 weeks? Their scouts would see it's Stannis, then have a warm cup of wine together, so... ? PS: sorry for length and if my writing is hard to comprehend :D I hope you do get my reasoning tho.