When the Supergirl series was first announced for CBS and word was that they'd cast Jeremy Jordan as Winn Schott, comic fans knew that he was going to be a bad guy — or so they thought.
The reason fans thought this is because in the comics, Winn Schott is the Toyman. And it made sense that we'd be introduced to a character that would become a villain — we'd just seen it on The Flash. Instead, we got a bit of a nerdy tech-support guy with a huge crush on Kara Danvers (Melissa Benoist) and was part of a love triangle with James Olsen (Mehcad Brooks) in the first season. Schott quickly became the guy-in-the-chair for Supergirl, helping her design her costume. Any idea that he would turn evil was wiped away in the episode where we meet his father, Winn Schott Sr. (Henry Czerny), AKA the Toyman.
Where he helped the DEO a few times in the first season, it wasn't until the move from CBS to the CW that Schott moved out of CatCo and became an agent alongside Alex Danvers (Chyler Leigh) and J'onn J'onzz (David Harewood). He would also help James become the Guardian and end up getting involved with with an alien woman named Lyra Strayd (Tamzin Merchant). And though we haven't seen her yet this season, it's believed they're still involved. Where the first season brought a few dangers to Winn's life, season two upped the anti, with him going to an alien planet, fighting an alien soldier and overall getting himself in a lot of danger. But he's also the guy with the funny line and the one most likely to get the answers the rest of the team needs.
It also seems like we're not done with his backstory. A recent casting announcement says that Laurie Metcalf (Roseanne, The Big Bang Theory) will be along later this season to play Winn's mom. You don't cast someone like that unless they're going to have an interesting character.
We may also get to see a different version of Winn in the Crisis on Earth-X crossover — at least one of the trailers made it look that way. But the Winn of Supergirl's Earth is the guy who is always there for his friends, standing up even when he's scared, and the first guy to make the joke or silly comment — and in a show about super-powered aliens and billionaire megalomaniacs, we're very thankful that he's there.
Supergirl airs Mondays at 8 p.m. ET on the CW.