#who is self-professed about not caring about rukia or being involved with any of this shit in any way

[bleachbleachbleach]

I wanna know what Ikkaku knows about Urahara:

[Bleach 087]

Like, do they... know each other? The visual suggests that someone in the scene knows Urahara was a captain, and it sure ain't Ichigo. So I feel like we're meant to understand that Ikkaku knows this.

Urahara's name also holds weight in terms of Ichigo's viability as an opponent, which suggests Ikkaku knows Urahara as someone other than some rando criminal, or just as a Mad Scientist type. It's Ichigo's movement that impresses Ikkaku, not his strategic craftiness.

I don't try that hard to keep the Gotei's 20th Century straight in my mind, but we do know that during TBTP Zaraki wasn't 11th Captain yet, and therefore Ikkaku may not have been in the Gotei at that point then, ether. (There's a whole dispersal of 11th backstory filler eps, which I've been assuming aren't in the manga in any form, but who knows, maybe some of this backstory info also holds true here, too. In the anime, Ikkaku and Yumichika follow Zaraki into the Gotei.)

In any case, apparently Ikkaku has a whole Seireitei family (see: TYBW), so maybe they were well-positioned for all the hot TBTP goss regardless of whether Ikkkau was enlisted at the time.

Or does everyone just know who Urahara is? Obviously, he's a poorly kept secret at least as far as his outpost goes; he's made a whole business out of it. But if Rukia knew he'd been a captain she doesn't harp on it.

And if there's something you can count on me for, it is knowledge of random-ass Hitsugaya panels:

[Bleach 237]

Hitsugaya says he doesn't know who Urahara is. Well, he's heard the rumors about Urahara, but says Urahara is someone whose true nature can't be ascertained. He probably does know what Urahara used to be a captain. He's heard that he's formidable, and probably isn't someone to let your guard down around. Which, really, is all the things we know Ikkaku knows about Urahara. Hitsugaya's just not willing to extrapolate further based on rumor alone. Maybe Ikkaku is.

But based on how Urahara's name influences the way Ikkaku chooses to fight Ichigo, I feel like Ikkaku is not operating solely on rumor, either. Someone's battle prowess/skill as a mentor doesn't seem like something he'd accept without firsthand knowledge, even if he's willing to roll with it for other stuff. So I feel like it's perfectly defensible to argue that even if Ikkaku wasn't actually in the Gotei while Urahara was in the picture, he still had an ~encounter (and probably not while Urahara was in his Innocent Shopkeeper era).

Maybe Ikkaku ran into Urahara in the woods when Urahara was off making an impression on Kuukaku [1][2]. Or Ikkaku's Seireitei family sic'd the Onmitsukidou on him while he was off playing hooky in Rukongai! Tons of fun possibilities!

Of course, this raises the time-honored question of what, if anything, anyone in the current Gotei knows about TBTP. Because it really seems like they know nothing, and didn't even know there was something to not know. But for a lot of them that might be an effect of their willingness to pretend they know nothing? So I feel like you could go in a lot of directions with that. Not to have blorbo disease again, but Hitsugaya seemed like he was learning Vizard Lore in real-time during the Winter War, so apparently it's not like, part of some kind of Area 51 folder you gain access to when you become a captain lol. YOU HAD TO BE THERE. (BUT ALSO SOMETIMES NOT EVEN THEN)