Oliver is the worst of that list.
House, Caesar, Ulysses? Hell, potentially even Benny....They all deserve respect. House, Caesar and Ulysses will tell you their plan and they'll justify it. They'll argue and show you they've done their homework, and while you may not agree with their conclusions, you should give them respect because what they say makes sense. To me, speaking with House, Caesar and Ulysses....it's as if the three of them were to show you a chalkboard, showing a mathematical equation as to why their actions are the best solution. The math is all there, and it's correct. It all adds up, just as they claim. BUT! But that does not mean there isn't another solution, another equation. Just because their equation is logically sound, doesn't mean you can't find another equation to apply that's also logically sound, but suits your style more.
And that's exactly how it is for me with those three. I have a lot of respect for them as they've put thought and reason behind their work, but I simply disagree with their goals, and thus I'll work on my own. Having said that, I'm not one to interrupt their work; let Caesar live and may he have a chance to lead his Legion to glory in Arizona, let Ulysses live and may he find new purpose.
And Benny? For what it's worth, even though he IS a snake that'll slit your throat if given the chance, I can't help but feel like he's got his moments of honesty. He's lying through his teeth when he says he'll work with you, sure, but when he's talking about his dedication to his plan and his desire for Indy Vegas? Maybe I'm stupid, but I believe him. In the face of death, when he's out of options to slit your throat, he doesn't desperately try to weasel his way out and keep going; no, he lets you in on his plan and encourages you to see it through. That to me says that although Benny maybe be absolutely ruthless in seeing his plan through, this is bigger than just him and his ambitions; he's serious about the need for an Indy Vegas, though we may never know why. But he truly believes in it and every throat he slits, he does it for a cause he believes in. If nothing else, you gotta give him that.
And who is Oliver? Just a child with a gun. He's an idiot who wants nothing more than fame and glory, the "why" of it doesn't matter. Such an ideology in the hands of a man with that much influence and power is dangerous. He's wreckless, careless and negligent, and with him in such a position of power, a lot of people are likely to die without the man ever stopping to justify those deaths, only caring about how much money and power he gains from it all.
And thus, I found myself saying "eh, what the hell" when I saw the option to toss him off the Dam.