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So far on Supergirl, Winn Schott has been a valued member of Kara’s inner circle, both for his computer skills and occasional moments of counseling. Despite his crush for Kara proving a source for frustration, he’s mostly been a lighter character, known for dropping sporadic humorous comments. That will start to change once his father Winslow Sr., a.k.a. The Toyman (played by Henry Czerny), breaks out of prison and comes back into his life.
As any Superman fan will tell you, Toyman is not a pleasant character, and Winn portrayer Jeremy Jordan said that his character’s relationship with his father is equally unpleasant, drawing a comparison with Kara’s Kryptonian parents. He explained:
It parallels Kara’s relationship [with her birth parents] a bit, because she feels abandoned even though they had to do what they had to do. For Winn, it was abandonment without a reason and without understanding. We’ll learn a little more about why and what that was. He’s definitely holding on to some deep, dark emotions when it comes to confronting his dad that are brought to the surface very quickly.
Jordan also told TV Line that Winn’s issues with his father will have a “ripple effect” across the rest of Season 1, and viewers will see that the character’s lightheartedness is “compensating for something.”
Fans learned about Winn’s fractured relationship with his father during “Livewire,” when he mentioned to Kara that Winslow Sr. was in prison. Like his comic book counterpart, Supergirl’s Toyman likes to weaponize children’s playthings for use in his crimes. When the villain arrives in National City, he’ll seek out his son for unknown reasons. That could mean anything from sincerely trying to repair their relationship to using Winn for a nefarious scheme. Given the official pictures showing Winn tied up, I’m guessing the latter. Whatever’s going on, don’t get your hopes up about seeing them on good terms by the end of the episode.
Jordan also didn’t rule out the possibility that Winn may one day become a bad guy, though that likely wouldn’t happen for a long time. So far, DC TV’s track record of having new characters with a familiar last name turn evil, specifically Arrow’s Tommy Merlyn and The Flash’s Eddie Thawne, hasn’t been stellar (not that we’re complaining). Perhaps Winn will be the one who finally makes the jump. Although he has a family of sorts with Kara and the other Team Supergirl members, Jordan did say that the dark side is in Winn’s blood, so if something happens to Winslow Sr on the series, unfortunate circumstances might eventually lead to Winn becoming Toyman 2.0.
You can catch Winn’s reunion with his father on Supergirl tonight at 8 p.m. EST on CBS.