From the start, James Olsen has been one of Supergirl's more clever subversions of the vast and often unwieldy Superman mythos that it was inevitably going to be saddled with. Where most incarnations of this particular property have been broadly concerned with establishing how different the heroine is from her cousin, this series has been preoccupied with establishing Kara as a more direct Superman analog and then playing around with the differences: Her Luthor is female (and might be a friend), she's a reporter but not at all gifted as one, etc.
But "Superman's Pal" Jimmy Olsen as a handsome would-be love interest and now her boss? That's quite a turnaround. And having him now adopt a superhero identity of his own? It may not be the first time a Superman property has pulled that particular trigger, but it doesn't make it any less eyebrow-raising.
It's also not 100% clear how much of this was planned. Supergirl was originally developed as a standalone series for CBS, and its setup reflected that approach: A deliberately conventional Millennial "working girl" comedy-drama where the doggedly upbeat heroine was moonlighting as a super-powered crimefighter. But since the show's move to The CW, it's been hard not to read a lot of the series' season 2 plot developments (mainly the greater focus on an expanding cast of regular heroes) as an attempt to fall into line with the rest of the so-called "Arrowverse."
Olsen's arc certainly feels like that: After spending most of season 1 in a gradual, organic build to a romance storyline with Kara, season 2 opened with the relationship being abruptly cut-off for a new direction that's on one level all about adding another costumed hero to the mix... but on a deeper level all about emasculation-anxiety. Smarting from getting dumped by Kara only to see her getting friendly with fellow superhuman Mon-El, undercut by gruff old-schooler Snapper Carr in his new position as boss at CatCo and generally glum about a lifetime of sidekick-duty, he's rebuilt himself as the armored vigilante The Guardian.
To be sure, Jimmy Olsen making himself into a superhero is itself a time-honored Superman Family tradition (Elastic-Lad, Mr. Action and Flamebird are only a few of his alternate identities), but it's rarely come with the kind of eyebrow-raising story baggage that it does here. It's easy to see why The Guardian was thought to be a good fit for the CW show; as conceived for Supergirl, he looks like a cross between Iron Man and Captain America with a smattering of Batman-esque gadgetry sprinkled in. And the (for now) secretive nature of his identity (Olsen and Winn are in on it together, but Olsen doesn't know Winn told Alex - who hasn't told anyone else... yet) has introduced a welcome element of mistrust into the series' otherwise feel-good friendship party.
On the other hand, the whole angle so far feels poised right at the edge of being a bit on the creepy side - however unintentional. The idea of an ordinary human jumping into the superhero life in part because they've been left feeling inadequate by an unrequited superhero crush is an amusing spin on the material, but it's more than a little off-putting for the show to continually frame James and Winn (who was also a would-be paramour of Kara's in season 1) as standing together off to the side looking resentful of Kara and Mon-El, before heading out on their co-heroic missions.
Supergirl is a series that runs on the logic of all its seemingly-adult characters having the emotional outlook of teenagers, but two guys essentially teaming up to vent their romantic frustrations by beating up criminals is weirdly close to being the wrong kind of immature - especially if they try to draw it out too long.
Fortunately, drawing things out too long does not appear to be on Supergirl's Season 2 agenda: Major plot elements like the true identity of Miss Martian, the fate of Jeremiah Danvers and the reveal of Lilian Luthor which could conceivably have driven entire season's worth of storylines have been raised and worked-out over the course of 2-3 episodes; ditto one-and-done (for now) debuts for A-list Superman foes like Metallo and The Parasite. It's the emotional storylines (Kara trying to reinvent herself as a reporter, Alex dawning realization of her sexuality and coming out journey) that get the long build, versus the more plot-driven material.
So maybe that means the current status quo for James Olsen and The Guardian will play itself out and move on to the next logical step (i.e. what happens when Kara figures it out) without dragging Team Guardian's weirdly passive-aggressive behavior out to the point where it becomes (more) absurd - particularly if Kara's reaction is to point out how this behavior looks from the outside.
But that still doesn't precisely answer where The Guardian goes from here. Does the identity keep going as part of the series running mythos, effectively giving all three of our regular CatCo-based characters separate superhero gigs? Does he give it up and resign himself to being more effective in his daytime line of work, thus adding another swing-and-a-miss for what started out as a "winner" version of Jimmy Olsen? Do they split the difference and make the Guardian gear something James and Winn bust out only on rare occasions? Hell, will they go for a "sad ending" and use a downer fate for The Guardian as a way to send the character packing for whatever reason?
So far, Supergirl has done an admirable job of balancing a need to shake up the Superman mythos with a respect for where these characters have come from, and there's no reason to assume this wouldn't continue to be true for whatever the plan is for both James Olsen and The Guardian. But even still, it's not surprising that fans don't quite know what to make of the storyline yet - hopefully, the writers do.
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