Do you think Jack was a good leader? Maybe I’m biased because I really like him but I do feel like he did a fairly good job given the circumstances (magical island, everybody periodically pursuing their own agenda, John Locke) which is why I’ve always kind of hated Sawyer’s “I think, you didn’t and a bunch of people died” speech in s5. The circumstances are completely different!
I remember that some time ago I wrote something about this topic that went something like this: everybody on that island wants a leader while ALSO wanting to go do the stuff they want to do without having to bear any of the consequences... The line between "leader" and "scapegoat" has never been more blurred than in LOST and I personally think many people very much miss this specific aspect of the story.
In a way, I do think Jack was a good leader, both in the sense that he had the potentiality to be one (which is the main thesis statement of his arc, Jack's own self-actualization as "The Leader", "The Hero" etc.) and in the more pragmatic sense that I do think he was the best fit for the job on that island (I've also covered the Jack vs Sayid of it all, if you're interested).
The thing you've mentioned is interesting because S5 is all about doubting Jack's ability to lead. The whole of S5 is his "dark night of the soul" (which actually started in S4 but chronologically it happens 3 years after the events of S4, so during the timeline of S5) so Sawyer's line kinda makes sense bc Jack is being completely out of his goddamn mind the whole time (also see Juliet calling Jack out in the shower in "Whatever happened, happened" or "He's Our You", if I'm not mistaken).
So S5 Jack as leader is kinda meh, but S1 to S4 Jack is a good leader, imho. like, OBVIOUSLY we KNOW that he's wrong! because we know about the fact that the island is INDEED "magic" or whatever. Like, in this respect, we know that John IS right, although many people just fail to see how WRONG he also is because of his tragic sob story (I love John but his backstory is so melodramatic to kinda verge on the pathetic at times).
And this is not a flaw in the story, this is how the story is supposed to be, because Jack is the protagonist and we have to "live through" him to actually "get" the story. So we must see him fail, even though, on a logical and rational plane, he is indeed right: of course he wants to LEAVE the island! of course he wants to SAVE people! of course he's PISSED OFF that people just don't listen to him WHILE demanding him to make good calls. he's in an impossible position because the story IS about the stupid expectations people have about someone coming to rescue them from all their troubles. Nobody will come because we all have to work together to make it! (the "Live together, die alone" motto which, unfortunately, taken like this, ie. out of his context, takes on a different, grimmer meaning).
So yeah, of course Jack Shepard is a good leader in a story about good vs bad and individualism vs community! In 2026 people are finally waking up and seeing the light because now we're more used to this type of complex heroes, but back in the early 2000s very few people understood Jack from a narrative pov (not to mention a psychological one) so it's always been unfair that people hated on him and called him a bluff.
The action hero these people wanted was right under their nose and it was Kate but, of course, Kate being a woman meant that she was "annoying" so nobody was happy with her either.
Sometimes people just don't want to think while they consume media and only project their own shit on the stuff they're watching. I mean, fine, some projection is always accounted for but after a while you simply must accept that what you're watching in your head is NOT what the rest of us is watching on the screen!
thanks for the ask, always lovely to receive one! ;)