If so, the Sisko's giving up an entire space station is definitely a big one.
Yes, that was a major retreat. But Sisko did return to DS9.
One of the things that I found memorable about Sisko's retreat was the stirring departing speech that he gave to those DS9 folks who were staying behind. Star Trek captains are adept at speechifying.
The line in his speech, "And I promise, I will not rest until I stand with you again ... here ... in this place where I belong" was reminiscent of General Douglas MacArthur's, "I shall return" declaration, after MacArthur retreated from the Philippines during WW2.
According to Ron Moore, the writer(s) who wrote Sisko's speech were "definitely inspired by it in concept".
But, unlike the fictional Sisko retreat, where all Starfleet personnel and their families, except for Jake, successfully withdrew from DS9, only a very small number of MacArthur's people got out of the Philippines with him. The rest of the soldiers under MacArthur's command could not escape, and they were forced to surrender to the Japanese. And those men were treated brutally while in captivity.
Of course, MacArthur, like Sisko, did return triumphantly. He led Allied forces in retaking the islands from Japanese control. That's my boring history lesson of the day.
Was Kirk a coward?
(image from Trekcore)
Well, in this scene in "Spectre of the Gun", Kirk knowingly walked into a lion's den, and he wound up sheepishly putting his hands up.
Kirk refused to draw his gun when challenged. Kirk retreated from a potential gun fight with Wyatt Earp. Was he being wise or cowardly?
This is what Morgan Earp had to say about Kirk, aka Clanton, "I always said you was yellow". And Morgan wasn't referring to the color of Kirk's shirt.