Both sides liked classic Trek and Next Gen because the authors wrote both sides of the issues.

For example in The Pegasus, Picard upholds the treaty that prevents cloaking because the Federation gets trust and cooperation by honoring its word, while Pressman is totally correct that it's the stupidest agreement they ever made - the writers even name it the Treaty of Algeron, which is not coincidentally a single letter from Algernon, the mouse that was temporarily super smart but soon tragically lost all his intelligence. Just like how the treaty seemed smart at the time and by Pressman's time had become moronic.

In The Wounded, Picard turns a blind eye to all the evidence that the Kardasians are preparing to attack the Federation - the high energy shielding on cargo ships, the militarily strategic location, ships with no transponders - even though at the end we see that he only acted dumb on orders from Starfleet to preserve the peace when he doesn't offer reparations for the dead but rather a 'you fucked around and found out' message. The writers ensured we knew that the "rogue" captain was actually correct in everything he said: the Kardasians were arming, starfleet didn't know what was going on, the bureaucracy wouldn't act in time, lives were at stake, he did have to act now, he did prevent war (or at least delay it).

Both of these guys while officially portrayed as the 'bad guy' were also completely justified and correct from a utilitarian point of view. In new trek they would just be cartoon bad guys.