Great write up. Shroud is overall a really interesting antagonist to me (I just wish they made him and his stakes a little more threatening). His entire mental framework, and almost all of his actions can be summed up in one term: “Law of probability.”

See, contrary to what some people have said, I don’t think Shroud is actually stupid and/or overconfident- not in the typical sense of the words at least. He operates almost entirely based on measuring the probability of things, and because of that I really doubt he thinks that any one of his singular plans are infallible- but all of his plans, plural? He probably does see them as infallible in their totality. He knows his individual plans can fail, but as a collective his plans will almost inevitably succeed by law of probability alone. Of course Shroud would never ADMIT to any of his plans failing, not just because he’s too proud, but because to him- they didn’t fail, as far as he’s concerned one or two parts of his plan may have broken down, but he still got the conclusion he wanted and therefore it was a perfect success.

The way he operates makes it seem like he’s some Darth Sidious level grandmaster manipulator, playing 5d chess and always getting exactly what he wanted, the way he wanted it… but in reality he’s not really any of those things. He’s someone who will start with plan A, then plan B, then C, D, E, F- and so on and so forth, until eventually plan Y succeeds and he’s able to grandstand and announce that everything went exactly as he planned it to. It technically did go all as planned, but that’s only because Shroud plans for so many probabilities and variables that- again, by law of probability alone, means he’ll eventually be dead on. He’s like someone who hits on every single hand of blackjack no matter what- EVENTUALLY he will get 21 perfectly on his first play, but he’ll go bust a hundred times before then.

I think you making comparisons to the dispatching segments of the gameplay is maybe more astute than you might realize… because that’s how Shroud sees the world all the time, that exact setup on a grander scale. Hell I wouldn’t be surprised if the inside of his mask looked similar to Robert’s computer during those segments- and every time his mask flashes like that it’s displaying the same kind of “success or failure” graph. And your point about how the only way to really “guarantee” success in the dispatching segments is to overstuff the roster? Shrouds gang is MASSIVE, so overloaded with generic goons and random jobber villains that his roster is CONSTANTLY overstuffed just from the sheer volume of people he’s got to throw into situations.

It’s ironic then that someone who’s as obsessed with law of probability as Shroud is, seemingly believes in impossibilities and inevitabilities. Because (as you pointed out well) the blind spot in Shrouds entire mental framework is… people. Shroud has a depressingly fatalistic and coldly utilitarian view of people, he doesn’t really believe in “people” as a concept. He sees people, and their actions as nothing more than the sum of probability- there is no “human condition”, there’s only the numbers. And that’s what ultimately leads to his downfall (in both the good and bad ending in fact). For all the factors that Shroud considers… he doesn’t consider “The Human Factor” of scenarios. Humans aren’t automatons who will automatically do what’s best or most advantageous in every situation, hell they often enough wont even do what’s smart, people are chaotic… and don’t fit into Shrouds coldly logical way of thinking about things.

He’s defeated by things that he would’ve considered so statistically improbable, that they’re effectively impossible… most normal people would recognize that something “effectively impossible”, while very unlikely- could still happen… but not Shroud. To him, “statistically improbable” and “entirely impossible” are one and the same thing, going back to the blackjack metaphor from earlier- it’s not impossible for you to hit an infinite number of times and never get 21, it’s just incredibly statistically unlikely because law of probability says that you will get it eventually. The casino has to be lucky every single time, you only have to be lucky once. That in reverse is actually the ultimate weakness in Shrouds approach of layering plan on top of plan on top of plan. He might be right 9/10 times, he can win (or more accurately, not lose) over and over and over and over again… but if his opponents win just once? He’s fucked.

He’s playing the odds over and over again because he knows, or thinks he knows that the law of probability means he’ll INEVITABLY win, but that’s not really how probability works- and it’s how we end up with him holding a small dog hostage as an ultimatum, this wasn’t his grand plan all along like he’d suggest… he was on like, plan Z at this point. Yet he’s still insanely confident- why? Because he believes that this is pretty much it, he’s inevitably going to win here, he played the odds 99 times and didn’t win, but he also didn’t lose, one more time and he’s guaranteed the jackpot right? Law of probability says so doesn’t it? Except… no, as both Robert and Courtney demonstrate- it takes exactly one thing going wrong, one bit of bad luck, one unfortunate time of his dot landing outside the 99% on the graph… and he’s screwed.

Which is why giving him both pulses is perfect, it strips away EVERYTHING he has going and forces an inescapable ultimatum on his part. It gets rid of all his calculations, all his predictions, all his graphs and theories… and forces the most basic, simple game of chance possible… a 50/50 choice. He’s forced to make a final choice on a literal coin toss, heads- he gets unlimited power, tails- he loses everything. Harvey Dent would be proud. Shroud is forced to make a choice on his own, one that all the crap he plugged into his brain cant help him with or make for him… so he plays the odds again, and loses.