I’ve talked before about characters who are stealth favorites, the ones who don’t make a huge impression on me at first but who sort of sneak up on me in my regard until I can’t remember when I started loving them. In those instances, it’s fun to go back and rewatch from the beginning and realize how awesome they always were. But while I came to love Winn, he wouldn’t fall into that category for me. Instead, my appreciation for his character is something that developed very specifically from writing tweaks and personal development (some Winn-related spoilers.)
Don’t get me wrong: from the start, I can see Winn’s potential as a character. I always like a quippy tech guy, and I enjoy a non-powered best friend who’s in on the superhero’s secret and enthusiastically supportive. In Winn’s case, he takes to Kara’s secret identity like a fish to water, designing her suit and helping her find her footing in the early days of her superhero endeavors. On that same front, I like he demonstrates his worth to Team Supergirl even though he doesn’t have any powers and isn’t a badass like the similarly-non-powered Alex. He’s valuable, both for his skills on the team and for his support of Kara as a friend.
But there is a sizable stumbling block that gets in the way of me fully loving season 1 Winn, and that’s the Nice Guy factor. Now, I completely get Winn being into Kara, I do. Even before he finds out that she’s a powerful-as-all-get-out Kryptonian who can literally stop a plane from crashing, she’s utterly, adorably lovable. Any guy with good taste ought to have a thing for Kara. And I’m sympathetic that that can be tough, especially when he sees Kara developing a massive crush on James and bringing in the added awkwardness of them all working together. I do get it. But yeesh, I’ve had a lifetime of scenes of nice nerdy guys acting threatened by the bigger/more masculine would-be male love interest, purporting to be the female lead’s supportive friend while trying to subtly undermine the guy she’s into. And again, I get Winn being all up in his feelings over Kara, because she’s amazing, but that’s not a story I like watching. It’s not a good look for him, and it makes the storyline through a rough patch where things are strained and weird between him and Kara.
In season 2, with Winn’s move from Catco to the DEO, a lot of his more frustrating qualities get excised while retaining his good parts and adding more cool dynamics for his character. By this time, he’s fully made his peace with his crush on Kara and has come back around to being a real friend to Kara, not a guy who’s anxiously trying to evade the friend-zone. In this new setting and with Winn’s new perspective/maturity, he’s someone who can truly back Kara up, whether that means designing cool tech gadgets for her in the field, lending her an ear when she’s struggling, or standing up for her with others. Not to say that he’s perfect or that he never screws up or gets at odds with Kara again. But this shift in how he relates to Kara is just infinitely better, which makes for a major improvement.
Season 2 and beyond also opens Winn up to a lot of other interpersonal relationships on the show. Getting over his Kara-romance issues helps Winn interact with James in a healthier way, and they develop an engaging back-and-forth in their ensuing partnership when James recruits Winn to help make his Guardian armor. Relocating Winn to the DEO makes him J’onn’s employee, which is a lot of fun – no-nonsense J’onn and twitchy Winn is a delightful combo. And best of all, we get Winn’s kid brother/big sister dynamic with Alex. When Brainy took on the main tech-guy role after Winn’s departure at the end of season 3, his and Alex’s relationship became one of my favorites on the show, so it was good to be reminded of how much I like Winn-Alex on my last rewatch. The Winn-Brainy geek-off in season 3 is also a lot of fun.
In season 5, when Winn returns from his new home in the 31st century for an entertaining two-parter, it’s just wonderful to see him again. At the time, I hadn’t felt like I was noticeably missing him, as the series did a good job filling in those empty spaces, but as soon as he showed back up on my screen again, I was like, “Aww, Winn!” I really enjoy this story, seeing how Winn has changed/leveled up in his time away but also how seamlessly he falls back into his old friendships; he, Kara, and Alex stopping to catch up in the middle of an active crisis makes me grin so hard. When I think back to season 1, there were plenty of times where I could’ve thought, “This guy could leave tomorrow and I wouldn’t miss him,” so it’s a testament to how well Winn grew and changed that I was so happy when “Back from the Future” rolled around.
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