Don't flag frivolously. But... If it offends you, please do flag. The folks handling flags are expected to do the same. That's how we resolve these things; there's no abstract measure of offense, it boils down to what the folks using the system find objectionable. On main, we renamed the flag to "rude or abusive", which is probably a bit easier to evaluate.

Re-adding one relevant comment: the flag to which your above-quoted 'PSA' was presumably a response (the only flag raised in the Bridge at around the same time) was on a post which called a specific celebrity a "jackass" and mentioned this as the reason they might perform at Donald Trump's inauguration. That is rude, and is not "merely express[ing] a particular political viewpoint".

Some people might probably be surprised that unlike on facebook, on StackExchange you can't flag particular opinion or fact away.

@randal'thor: Oddly enough, there were several flags at the time, not merely one. I remember at least four or five flags were raised. Perhaps the system doesn't keep track of flags that are dismissed as invalid?

I don't doubt that this particular message is rude and should be flagged. I did distinctly recall several flags with seconds of each other, though. I'm not sure why you're not seeing them. Perhaps those flags were elsewhere on chat? Note that the flags appear to have originated from the transcript page, which may point to a bug in the chat mod tools.

@bwDraco My mistake: there were some earlier messages which were flagged around the same time. (I missed them originally because the list is ordered by time posted, not time flagged.) To wit: one saying "The {Republicans'} base is already going looney tunes on the fact Trump is backpedaling for all he's worth", and three (!) calling specific politicians "punchable" (link to one of these, though it's probably invisible to non-mods as those flags were validated).

I dismissed the "punchable" ones as invalid (perhaps wrongly) because they seemed "meh" to me. The first one, however, is definitely not offensive. The flood of flags did lead me to question the motive of the flagger as being politically motivated rather than genuinely trying to remove offensive content, which is probably the real reason I considered them invalid.

On the other hand, if things get to where a bunch of people are fighting and getting tempted to flag each other, that might well be the sort of disrespectful conversation Shog is encouraging us to avoid, and intervention might well be in order. Things still shouldn't be flagged purely because of personal disagreement, but in many of these "flags flying" situations, a custom moderator flag asking for help calming things down might still have been the best course.

Those messages you linked to do seem to fall afoul of the Be Nice policy, which applies to politicians. One of them calls Donald Trump "predictably stupid" and the other says he's a "shitty person" -- neither of them would be appropriate when applied to another user, so neither are they appropriate for politicians. Users are free to criticize politicians for their policies but that's not what these messages are doing.

At least one was ruled okay by a local mod. I do agree that none of those flagged messages were great, but the flagging of messages that are even borderline offensive really makes it look like it's politically motivated.

What if flagging something would cost you rep if not ruled valid? Maybe with the option of "appealing" the decision (panel of 3 moderators) at the cost of more rep if also dismissed, but with rep or "for greater good" badge if approved on appeal.

@Quarktaart - better yet, ban people (at least from flag reviewing) for dismissing flags that are later ruled actually offensive.

@bwDraco - that's why flags have an option to ignore them. For when the reviewer isn't sure and isn't willing to investigate context.

@DVK: I'll be more careful in the future. However, please bear in mind that not every user finds the same content offensive. At least some of the messages in question were not deleted, and that the messages were apparently insulting or offensive in a veiled, rather than overt, manner, making them particularly difficult to accurately assess.

@bwDraco - this is most certainly a tremendous improvement after the edit. Thanks, and reversing my vote.

@bwDraco - having said that, you still seem to retain the same fundamental misconception (even if it isn't emphacised in the new answer), that just because you (or a mod who themselves posted offensive chat comments in the past) didn't find a specific message offensive, it doesn't mean that the person flagging fagged merely out of political disagreement and not because they don't find it offensive. I can go through every flag you find incorrect that you mentioned and point out specific factual reason why it was offensive, and none of the reasons had to do with disagreements on substance.

@bwDraco - in general, the fact that flags weren't validated isn't always a sign they were wrong. I remember past cases where the rooms had not-nice culture (not even related to politics), claiming that objectively offensive content was "OK" by room standards till people escalated the issue. The reason I strongly object to your stance is specifically because it hurts the people fighting against entrenched offensive culture the most.

Imagine a Linux-dominated set of chat rooms (I know it's hard to imagine on StackExchange given their MS stack). It's not unexpected that any flags on messages that are not-nice towards Ballmer or Gates wouldn't be universally agreed as offensive, especially during SCO days etc... Which in no way speaks to the messages offensiveness or not, merely dominant mood/attitide in the community.

Ugh.. this is getting too long and too chatty. Where's the "move comment thread to chat" link when one needs it?