I didn’t include this one in my Season 5 Finale Posting Spree, because Littlefinger didn’t appear in the episode, but this is still an open question for the end of Season 5: where is Littlefinger now, and what is he doing?
We haven’t seen him since Episode 7, in which he met with Olenna in the wreckage of his brothel.
Episode 6 showed him doing what is arguably the most Littlefinger-ish thing he has ever done. He meets with Cersei, acts like Sansa got to Winterfell all by herself, and offers to do the Iron Throne a favor. The deal with Cersei is that she names him Warden of the North, then he goes up there with his Arryn knights soon after the battle between King Stannis and the Boltons, and he snags Winterfell from whichever side won the battle, assuming it was a close battle and the victor suffered a lot of casualties. This is a very big assumption, and we’ll get back to it later. He promises Cersei that he’ll put Sansa’s head on a spike. I don’t believe for a moment that he means to do any such thing, but that’s what he tells Cersei to get her to name him Warden of the North. He promises to get the lion flying over Winterfell.
Next we see him is Episode 7, in which he has a private discussion with Olenna Tyrell, meeting in what remains of his brothel after the Sparrows did their number on it. He doesn’t seem to have seen that coming. I wonder how he’ll cope with the loss of income. Anyway, there’s some posturing between him and Olenna, as two of her grandchildren have been arrested, and he was her co-conspirator in killing Joffrey, but he promises to give her a handsome young man, as he gave to Cersei. The implication is that he introduced Cersei to Olyvar, who was vital in having Loras and Margaery arrested, and now he’s providing Lancel as a witness against Cersei. So he planned all along for Cersei to be arrested right after she gave him a new position.
Once Cersei was arrested, then I guess the plan was to take his knights up to Winterfell, have them kill Ramsay Bolton if Stannis hadn’t already taken care of him, claim his seat as Warden of the North, and take Sansa to wife. He gets yet another castle, control over yet another province of the realm, and he gets his sweet Cat’s daughter’s pretty ass on his greedy lap.
We don’t see him for the rest of the season. What is he doing now, I wonder? One major complicating factor is that he was assuming Stannis would put up a better fight in marching on Winterfell. Littlefinger’s scheme of re-capturing Winterfell presupposed that both sides would suffer a lot of casualties, so the victor would be unprepared for a fresh attack.
That didn’t work out so well, did it? He hadn’t anticipated Stannis losing so much of his army ahead of the attack. What remained of his host was obliterated, while the Boltons are still in good shape. And I’m sure Littlefinger knows how big an army the Boltons brought to the fight. He was at Winterfell not long before the battle. Since it wasn’t a close fight, the Bolton host would not fall easily to the Arryn knights.
The Boltons don’t seem to have lost many knights in the battle, but they DID lose Sansa and Theon. And you can bet they’re not the least bit happy about that. They’re making it their business to get their remaining Stark back in the castle ASAP, or at least find her body. I suspect Ramsay is flaying some household knight who failed to stop his pretty bride and Loyal Reek from jumping off the wall. But mostly they want to find her.
What Littlefinger does next depends a lot on what he knows about the situation at Winterfell. I’m sure he’ll find out how the battle went, and when he does, he’ll postpone his plans to take the castle. He’s way too knowledgeable not to find out about Stannis marching with a piddling army of foot soldiers and getting utterly annihilated. I don’t know whether he’ll hear about Sansa’s escape, though.
If he hears that Sansa jumped off the castle wall and her body hasn’t been found, I’m sure Littlefinger will be interested in finding her. He’ll go up there with some knights and try to figure out what happened to her. And he’ll let the Boltons think he’s there as their ally.
(By this point, he probably still hasn’t figured out that Ramsay is a disgusting sadistic monster who kept Sansa locked in her chamber all day, brutalized her by night, and would have been happy to dismember her.)
If he doesn’t hear about Sansa leaving the castle, though, then he’ll probably stay put in King’s Landing. He’ll hold off on re-taking Winterfell until the Boltons suffer some other vulnerability for him to exploit. Maybe he’ll focus on rebuilding his brothel. Or he’ll take an interest in Cersei’s trial. Now that Uncle Kevan is Lord Regent and Protector of the Realm, Littlefinger might want to get to know him.
Uncle Kevan probably doesn’t know about Littlefinger’s deal with Cersei. He’s not supposed to know. I’m sure he wants to have the lion flying over Winterfell, but he doesn’t trust Littlefinger to make that happen, because Littlefinger is not trustworthy.