(Spoilers ADWD) I think most people overlook one Brotherhood spy, whose name is... (Now with a different tag!)

Note: Reposted because I apparently used the wrong spoiler tag.

Hildy.

I think this is a pretty obvious observation, but I hadn’t seen anyone make it here, so I thought I’d write it up.

Who?

You know. Hildy. The washerwoman/camp follower/whore who’s getting plowed by Jonos Bracken in ADWD 48.

Wait, what?

Okay, bear with me. The Brotherhood Without Banners uses innocuous-seeming smallfolk as spies, who they plant in Lannister/Frey-aligned camps across the Riverlands. After all, Jaime encountered Tom o’Sevens at Riverrun. Tom had already managed to insinuate himself into the Frey camp, and by the time Jaime departed, he had been left to the Freys as their singer (after spending a conspicuous amount of time alone with Edmure). And to top it all off, he likely gave the BWB a heads up so they could ambush Ryman Frey when he left camp.

Hildy is doing the exact same thing. She has infiltrated the Bracken camp to monitor the siege at Raventree Hall. As with Tom, no one would suspect her of anything. Washerwomen and singers are common fixtures in a siege camp. And like Tom, she finds cause to place herself where she has the best access to information. Specifically, she plants herself in Lord Bracken’s command tent.

Okay, but isn’t this just supposition? There are whores everywhere. What makes this one a BWB spy?

Unlike Tom, we don’t know that Hildy is working for the BWB. But there are other indicators that she’s no simple whore. First, she has a conspicuous amount of page space, and a name to boot. Few camp followers can say the same. Second, she’s quite the actress. She plays at modesty when Jaime busts in on her and Lord Jonos, and once Jaime calls her out, she starts in on him with thinly veiled flirtation and attempts at seduction. Compare her to Ryman Frey’s washerwoman, the Queen of Whores. Where she is crass and unapologetic, Hildy is witty and subtle. I humbly submit that we’re seeing more than a zany, clever whore. I think we’re seeing tradecraft in action.

But the reason I most suspect Hildy of being a BWB agent is what happens after Jaime leaves Raventree that evening. As you recall, Jaime speaks with Lord Jonos (after Hildy is dismissed), promptly treats with Tytos Blackwood, takes one of his sons as hostage, and leaves Raventree before dusk. He and his men then take camp in nearby Pennytree (the smallfolk having taken refuge in their sturdy keep) and lo and behold, Brienne appears out of thin air.

The timing is uncanny. It’s too coincidental to be coincidence. Someone at Raventree Hall alerted the BWB that Jaime was in the area, and I can’t think it would have been anyone but Hildy. Bracken’s out—he’s on the same side as Jaime. I doubt it was a Blackwood, either. They’ve been under siege after all, and didn’t know Jaime was around until he came to Lord Tytos that afternoon. There wasn’t enough time for Lord Tytos to alert the BWB, and for the BWB to then send men to overtake Jaime. I also doubt it was the people of Pennytree, who are hiding in their keep, and who wouldn’t have known Jaime Lannister was present until he made himself known. (Note: I’m sure that the Blackwoods and Pennytree...ites could have seen Lannister banners approaching. But the fact that the BWB sent Brienne means they knew Jaime specifically was among the Lannister men. That’s a fact that could only be confirmed by someone who actually encountered him.)

That leaves Hildy. She left Jonos Bracken’s pavilion only minutes after Jaime arrived. If she got word to the BWB straightaway, they would have had all day to picket the surrounding area with scouts, and send Brienne to Jaime directly.

Oh, okay. Great catch, u/TheRockefellers!

Thanks!

tl;dr: Hildy, Lord Bracken’s camp follower, is a BWB plant who ratted out Jaime to the Brotherhood, which is why Brienne conveniently appears at Pennytree.

Edit: A lot of people have asked, "Couldn't Tom o'Sevens just given the BWB a heads up when Jaime left Riverrun?" Yeah, sure. It seems pretty likely. But Tom also knows that part of the reason Jaime is moving in force is to draw attention away from Edmure Tully's convoy. So Tom already knows that Jaime's trying to lure the BWB into a conflict. That being the case, it's even more imperative that someone at Raventree confirm Jaime's presence in person.

And in any event, it doesn't have to be an either/or situation. The way I see it, it's quite likely that the BWB would want spies in both camps.