If Picard had commanded the Dominion War...

We already got part of the answer. In Insurrection, Picard and his crew were sent on an archaeological mission. In the flagship and all.

TNG was just too nice and was too set into trying to remind us that the Enterprise was a ship of exploration.

TNG had its style, DS9 and the others had their own.

No way would Picard would trick the Romulans into the war. And that was a turning point in the war.

Picard might have found a way to beat the Dominion, but it would have been a lot different.

 

French jokes and Picard's tendency to surrender aside..... what do you think Picard would do with the Jack Pack presenting their Inevitable Doom Scenario to him?

 

I think in this case Picard would be stubborn and want to fight on. He's been shown to be really stubborn in some situations, like in First Contact, where 21st century human of all people, had to convince him how stubborn he was being.

After a loooong (but interesting) philosophical discussion/debate on it first, I think Picard would say something similar to what Sisko said.

Still it's a wonder did Starfleet sent Picard and flagship to study ancient ruins instead of fighting in the war.

 

Pee-KARD would have the Female SS to go rock and ancient pot hunting on LesserKnown IV. After the mission, she would have said, "F this why do we want to conquer these nerds"