Picard was ordered to negoitate with with Evora. Obeying that order would not make him a "bad guy". Perhaps they'd just had a stressful time liberating Betazed and then Starfleet sent them to use Picard's legendary diplomacy skills on a new strategic ally.
Well, then Picard's superiors become the villains, and Picard their unquestioning henchman. Not much of an improvement there. And still doesn't explain why Picard would be allowed to take his battleship with him for this holiday.
Implying that there's a war going on.
The implication is all wrong - in the movie, the UFP is not embroiled in anything, and what Picard laments is that the negotiations will stop him (and his battleship) from doing archaeology for the next X months.
It's not a case of our heroes doing something else in between fighting events. It's a case of the heroes doing nothing
but "something else", mission after mission, and keeping their large and well-armed juggernaut to themselves while some poor sod has to fly a
Miranda. If the Starfleet CinC sees nothing wrong with that, I'm quite ready to take his, her or its place, even if it wreaks havoc with my holiday plans.
This line implies that (as said above), it's after the battle of Cardassia Prime, but before the signing of the peace treaty.
There is no such time interval in the Trek universe, though. Remember that Dukat and Winn go to the Fire Caves before the attack on Cardassia Prime even starts - and are still at it after the treaty is signed.
Whatever negotiating is going on is apparently taking place after the signing event for peace/truce treaty that we witnessed in the episode, hence no fighting is going on and all is well in the world of internal continuity.
That is, a more solid peace treaty might have been signed some time after the conclusion of the war, with the negotiations to that end ongoing in ST:INS - but this would be a separate event from the one seen in "What You Leave Behind".
If we suppose that Borg reference is to the First Contact bits from the 24th century, and we use the thousand-stardates-to-a-year, that puts Insurrection sometime around star date 52900, give or take.
Indeed. Although it's a bit difficult to figure out how the
Cardassians "challenged the UFP" within those two years no matter what. Of course, Rua'fo could be combining a mention of the puniest opponents in known space with a reference to a truly insignificant challenge just to add injury to insult...
Timo Saloniemi