He was also eager to hear about her first fight with an alien, Vartox.
A week later, Winn alerted Kara of a fire raging at the National City Port, and offered her comfort about the mistakes she made in her early superhero career.
Winn is later informed by Kara that Cat believes her to be Supergirl.
He has feelings for Kara and has unsuccessfully attempted on several occasions to ask her out or tell her about them.
Winn tried to downplay the importance of Maxwell Lord's public criticism of Supergirl, despite Lord being Winn's personal hero.
Winn was surprised when Kara revealed that James Olsen also knew her secret identity, but accepted that she'd need both of their help to prove to everyone that she knew what she was doing.
Winn agrees to help bypass Maxwell's security systems, for James to get in.
When Kara notices James' bruises which he had gotten from Maxwell Lord, Winn notes that Kara is talking like Astra, and instead needs to let him and James investigate and find another way to expose Maxwell. Winn has left a doll on his desk from his father, Winslow Schott Sr., who had broken out of prison.
Before this potentially damaging revelation is made public, with the help of James and Lucy, Winn figures out a way to get legally admissible evidence proving the leak came from the Chair of the Cat Co board.