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Are you going to argue that “no-holds-barred” – as in, fighting dirty – isn’t negative?

No, I'm going to argue that "no-holds-barred" is not "political operative" and that adjectives modify nouns. If you see the phrase "evil dog", are you going to assume that must mean all dogs are evil?

I'd also argue that you're wrong about what "no-holds-barred" means too. After all, this is actually from an article championing the person in question. You misread a compliment for an insult because you're operating on the preconceived notion that both "no-holds-barred" and "political operative" are negative terms when neither are.

Are you going to argue that the system providing little control and no remedy isn’t a bad thing?

No, I'm going to argue that this question has nothing to do with showing that "political operative" is a pejorative term.

The other three examples are too out-of-context to know if they were complimentary or derogatory.

That didn't stop you from trying to argue about these two above, when you believed that arguing about them out of context was in your favour. The other examples are just more inconvenient to try to twist into somehow showing "political operative" is a pejorative. And, as we've seen, context is not friendly to your assumption.

The article is mostly paywalled, but here’s a salient sentence from the first paragraph where it admits I’m right:

How do you go from "it’s wishful thinking to believe the public imagines political operatives and staffers to be like The West Wing" to "political operative is an insulting way to refer to political staffers or politicians"? This isn't even getting into how the term is clearly and explicitly used in the headline in a way that indicates it as a neutral term that just describes a job, and that it will be used that way throughout the article.

The other two things you cited are from self-described “political operatives” themselves, and of course nobody believes themself to be the villain!

People aren't going to refer to their jobs in a pejorative way either. Did you forget that you were trying to say calling someone a "smart politician" is better than calling someone a "political operative"? You weren't saying all politicians are bad so nobody would ever admit they were one.

Again, where are you getting the idea that "political operator" is a term with a negative connotation?

Are you going to argue that "no-holds-barred" -- as in, fighting dirty -- isn't negative?

No-holds-barred is about the rules of engagement, not an individual's fighting technique. If anything it's even more positive because it means they can hold their own against people who do fight dirty.

Are you going to argue that the system providing little control and no remedy isn't a bad thing?

It's only that way because it's the police chief who crossed the line. That's a specific instance of the combination of "police chief" and "political operative" where the system provides little control and no remedy.

It's good for a chuckle, although it's wishful thinking to believe the public imagines political operatives and staffers to be like The West Wing. They've probably got a bleaker impression than that..

You might as well say "lawyer" is negative because people have bleak impressions of them. Should those on our side avoid studying law because people will think negatively of them? No, obviously, studying law is crucial to the drafting of policy that benefits people.

Likewise, understanding politics and being effective at operating in the political sphere is crucial to actually making things better.

Your argument is bad and you should feel bad. We want skilled political operatives on our side. If you want to whisper your political dreams into a shoebox and make an inoffensive manifestation board, then bug off and do that. The rest of us actually want to accomplish something, and that requires political savvy.