Interesting theory. There is definitely something suspicious about Ochoku and the WG's involvement with Hachinosu.
Kaido's line about pirate betrayal continues to stick in my head about the Rocks pirate. Whether he betrayed them, or WB betrayed them, or Ochoku, or some combination of them, or if it even happened with them, remains to be seen.
But we do know a few more interesting things related to them as of the last chapter.
1. Ganzui and Silvers died and ended up as Moria's zombies
2. Shiki, WB, Kaido, and BM went on to be notable pirates on the seas
3. Stussy fucked off to MADS
4. Gloriosa went back to Amazon Lily
So that leaves out Marlon and Ochoku as for Rocks pirates we have little frame of reference for past Rocks' death. Let's table Marlon for a moment and focus only on Ochoku.
Ochoku went on to become the Admiral of Hachinosu. That's a very specific title, one that isn't particularly pirate-like and much more marine-like, to have control over a pirate island (and we know it was still designated as such because Law stole 100+ pirate hearts to prove his Warlord worthiness during the Rocky Port incident). That also begs the question why the Rocky Port, a passenger ship that had a king and nobility of a WG country on it, bore the same flag and affiliation of a smuggling ship with ties to Hachinosu?
Law assumed the ship he was hijacking was the smuggling ship veiling as a passenger ship using the same flag of a WG affiliated nation, only for that assumption to be wrong and hijacked a real one. He hijacked it to get to Hachinosu and steal the poneglyph there, Koby and BB caught wind of what was happening and showed up for their own purposes (Koby to save the Rocky Port civilians, BB to take Hachinosu).
So in totality, we know that Ochoku ended up as ruler of Hachinosu post Rocks (somehow), maintained it long enough during the era of the 4 Yonko such that they never took it from him, and apparently despite it being a pirate island was being visited by a smuggling ship with a WG affiliated country's flag on it? This, by the way, is after the WG had already slinked on to Hachinosu to steal its crown jewel, presumably to be used as a reward at God Valley. So the WG would not be unaware of how important an island it would be on top of the gold mines it has. Something doesn't add up, how could Ochoku be that powerful?
I yapped a lot here, but just to make it clear: I don't think Ochoku was directly working with the WG, but I do think much like his sons, he's cunning and not oblivious to important information. He used opportunities to his advantage to open up trade Mother Carmel-style with WG affiliated countries and enjoy a somehow perplexing amount of protection from his foes during his reign over Hachinosu. He was either individually strong as fuck, or had a really fucking good network of allies and crews that he gained workshopping shady deals with WG countries.
Oda will probably never deliver much on this topic, but I am curious what the fuck happened.