You are interpreting the word "collaborationist" so broadly as to make it entirely useless. Apparently you would think that every prisoner in a work camp is a collaborationist if they don't immediately cut their own throats. The system we live in is way too all encompassing to somehow fight from the outside. Some level of interaction with the system is a requirement just to survive, and fighting back against the system can require even more participation in that system. You are trying to defend yourself against being called a collaborationist by muddying the waters and making the word functionally useless. When I used the word, it was in reference to the actual rhetoric you are using that is directly related to the conflict between American workers and Oligarchs. The Oligarchs have setup a system where they can kill us en masse with total impunity, but fighting back is out of bounds. You are taking a stance that is entirely unnecessary to take for any other reason but to defend the rules that keep us trapped in a broken system.

This entire argument stems from my refusal to reduce a man to his occupation.

When state catches the killer and puts them in jail, is it reducing them to nothing but being a killer? When we take certain actions in life, that is going to have consequences in how society interacts with us in the future. This creep wasn't just a health insurance CEO, he was by many measures the worst health insurance CEO. He traded other people's lives for cash, and that should have consequences. That's not a failure to recognize the breadth of his humanity, it's saying that actions have consequences.

Was Thomas Jefferson an oppressor, a rebel, or a collaborationist?

Who said that everyone can only fit in a single box? That sure wasn't me, I will point out though that doing away with slavery (to the extent that we did anyways) involved killing a whole lot of slave owners.

I don’t believe in free will, so this argument is kind of moot for me.

I personally think that free will as a concept is inherently nonsensical, and therefore I don't have a position on it at all. I'll call that agreement to that point. However, I'm not convinced that the concept of morality is entirely dependent on the concept of free will. A machine with a faulty mechanism still just does what physics say it must do, but we still call it a malfunction (bad function) and expect it to be modified to work properly. Anyways, I don't really want to delve into a nuanced discussion of moral systems.

I beg to differ, just look at the New Deal. When the Great Depression happened,..They elected a progressive candidate in FDR...

Same war, different battle. That was a strategy that worked, to an extent. However, what works once in war doesn't always keep working. The oligarchs learned from FDR and, when we tried this again in 2020, it failed. American oligarchs have a stranglehold on the media and decades more knowledge in how to manipulate voters. Eventually we will need progressive representation, but a lot is going to have to happen to make that possible again. We might get lucky if Trump's presidency fails in the right ways. If nothing else, Trump is great as an agent of chaos. Maybe he shuffles the deck and suddenly we have a credible electoral strategy, but I'm not counting on it.

American society did not descend into lawlessness and anarchy.

I disagree. The rise of organized crime in the US didn't start with prohibition. It started because oligarch strategies to divide the public on ethnic lines effectively created a bunch of isolated resistance forces. It evolved into something else, but the justification these groups used was always that their group had been unfairly shut out of prosperity. If they weren't going to be given their due, then they would take it. It's more self serving than a targeted assassination, but it was definitely lawlessness and anarchy.

It’s also worth noting that FDR is exactly the kind of person that the current mob would be putting on the list of assassination targets.

So far, exactly one particularly bad oligarch has been assassinated. You are making some pretty wild assumptions based on a single data point. In an oblique way, this reminds me of your point on utilitarianism. We don't know with certainty what any action we take might lead to. Maybe this CEO was going to be the next FDR, or maybe the next Hitler. Maybe Trump will have a change of heart (or grow one) and be the next FDR himself. Anything is possible but, call me a skeptic. This is not a valid way to argue anything.

This is where you lose me. You can’t know these things. You can’t know the future 50 years in advance.

No, but I can know history, and I can see what's going on in the world around me. Wealth and power in this country are both almost entirely in the hands of psychopaths. The psychopaths have a global disinformation machine with effectively infinite funding. The harder we have pushed for change, the more effort they have put into dividing the people into subgroups and convincing them to fight each-other. It's a strategy that works extremely well. It's human nature that the only way to heal those divisions is to give people a common enemy, and that has to be the oligarchs. Moving society is like advancing the plot in a book. You can't convince the masses to do something because it is the smart thing to do. They need a narrative, and assassinations make for an interesting story. I guarantee you that the oligarchs are more concerned about that aspect of this event than anything else. Suddenly all these people across all of their carefully created subgroups are unified in expressing hatred for their actual enemies.