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I don’t know why you think he expected to be caught, I’d argue him being so reckless means he didn’t think he would be since players were mostly awful, if he was a little careful he would of likely never been caught unless his inside man turned on him.
While I do not believe for a second he “expected to be caught”, it is entirely possible that he believed that whatever conditions and circumstances that allowed for him to cheat like he did would be fixed eventually, not because he would be caught, but for any one of many possibilities - if it was simply the presence of an inside man with access and no oversight, maybe said man gets transferred to another position, or he’s removed from that position, or a new hire ends up, either accidentally or intentionally, removing the lack of oversight.
Maybe the room adds another camera that significantly hinders the ability to check phones during hands discreetly. If it’s a software problem, maybe a casino wide update removes whatever problematic part of the software enabled Postle.
They did remove cell phones at one point, and postle then came up with the bone conductor in his hat. He might not have known during his crotch theory optimal phase that the bone conductor thing would work, so he was operating under the assumption the room could easily decide to not allow cell phones and he’d be out of luck.
There’s also the possibility the inside man had such a significant role in the operation (and/or such a bad understanding of poker) that postle felt he needed to squeeze as much money as possible out of each game or the inside man was pushing or encouraging him to be as aggressive as possible in winning every possible dollar they could each session. Given what we know of JK’s lack of poker and his willingness to absolutely deny postle was cheating and deny that it was even possible to cheat, if JK was the inside man, that certainly is possible.
Now, I’m not saying that was his thought process for sure. I still think the most likely thing is that he’s a very short sighted moron who stumbled onto a situation (possibly not even being the one who came up with the idea) and never really gave a thought to not playing as aggressively and exploiting the situation as much as possible. There have many an absurd number of similar situations to this where a person stumbles onto a situation where he can essentially steal/cheat undetected for years, and the only reason he or she gets caught is that he steals too much or makes it too obvious. Getting caught due to shortsighted greed isn’t unique to postle. For Christ’s sake, “you can sheer a sheep many times but only skin him once” comes from the same basic concept.
It is true that when he first started out, he was very cautious and careful in regards to his phone. We know the session he began crotch theory optimal. He doesn’t start the session in CTO, but at some point, he begins fidgeting with his cell phone, placing it between his legs and looking around to see if others can see his phone. He did this for a decent amount of time. So at the very least, he understood he needed to take multiple steps to ensure the cell phone was obscured and he also tinkered with what seat to be in (I forget which one he settled on, but I do remember he eventually settled on one seat in particular).
Maybe someday we’ll find out.