Later, Winn, sitting in a van and watching the situation, helped James to fight Parasite. This weekend is the perfect opportunity to invite Lena on a camping trip. After Winn saw in the news that On Maaldoria, as Alex led the team to the fortress where Kara and Mon-El are being kept prisoner, Winn stayed at the portal to keep it open, where he was attacked by a Maaldorian whom he managed to defeat. Under the orders of Non, both he, James, and Kelly all jump off of CatCo, with Supergirl rescuing him and James, though failing to save Kelly. Kara Danvers : What? After seeing his death, his wife went to her son so she could be a part of his life again and explain everything, unfortunately, before he died he trained another in his criminal ways called Winn mentions to Kara and Alex when he returns from the future that he and wife Ayla named their daughter Mary after his mother though it was a toss up between that, Kara and Winnifred indicting they almost named their little girl after Winslow Sr and Winn himself.Winslow was apparently once a good father according to Winn, saying that they used to be inseparable but after his toy designs were taken from him he went insane and tried to kill his boss he had no regret or remorse for what he did. His father was Winslow Schott, Sr., aka Toyman, one of Superman's nemeses. He later tries to stop Siobhan aka Silver Banshee when she arrived at CatCo with Livewire to abduct Cat, though he is put to the ground by Siobhan's sonic scream. The hacker then came through the computer, though she soon retreated after Hank and Alex arrived. RELATED: Winn’s Back From the Future In Supergirl 5.11 Promo This week’s episode will pit Kara against a mysterious Toyman copycat. The two then tell Kara to accept defeat or die. At an arcade, Winn finds his father, however, as Cameron and her agents closes in on Winslow Sr., they are tricked by a wall of mirrors and tells Winn Jr. to leave as the mirrors collapse.

Winn checks on hospital records for Kara, revealing that the bomber's sick daughter was having all of her medical bills paid by Lord, leading Kara to confront him over his involvement in the attacks. During Reactron's attack Winn was almost crushed by a falling support beam, but was saved by Kara. Winn is also the husband of Ayla and father of Mary, the son of the late Winslow Schott Sr. and Mary McGowan, the best friend of James Olsen, and a good friend of Kara Danvers, Alex Danvers, J'onn J'onzz, Mon-El, Querl Dox, and Nura Nal, and the ex-boyfriend of Lyra Strayd and Siobhan Smythe. Kara has had a crush on Lena for years. After being informed of Kara's situation due to the creature, Winn and James were both concerned of what would happen to Kara after they pulled her out of her perfect fantasy. for examination after her fall from the roof. Winn is later informed by Kara that Cat believes her to be Supergirl. He criticizes her, reminding her that James has a girlfriend and claiming that when her powers return she won't ever have a normal life or relationship.

Winn later confronts James for lying to Kara about not having a lead on what Maxwell Lord was hiding. Mon-El competed in arm-wrestling with some guy and almost broke his arm, the other hit him in the face, but also got a hand injury, then Winn quickly took him out. There, Siobhan tells Winn that she had been blacklisted and she can't even get an interview though Winn believes Siobhan will be back on her feet. Agents of S.H.I.E.L.D. 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. Later, Winn found out that Livewire didn't escape from prison but had actually been kidnapped by a scientist to make Livewire soldiers and, despite also founding where he is hiding, Winn kept the information for himself later giving it to James (although being overheard by Mon-El) and leading indirectly to the three heroes eventual team-up. He criticizes her, reminding her that James has a girlfriend and claiming that when her powers return she won't ever have a normal life or relationship.He and James are forced to work together the next week when they and Kara are tasked by Cat with the delicate task of damage control when her email is hacked and made public. He has feelings for Kara and has unsuccessfully attempted on several occasions to ask her out or tell her about them. 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.

That evening, Kara told both Winn and James that she had always seen them as heroes even before they became vigilantes and that if they intended to continue, she will neither stop nor support them.

A few days later, Winn confronted James about the news saying the Guardian alleged killed a mugger as James stressed that he didn't kill him, Winn started panicking about getting caught and insisted they stop but James refused and promised they'd find the impostor. Thought it was interrupted by a pod flying in the sky catching their attention, causing Kara and J'onn to leave to check it out.

On Maaldoria, as Alex led the team to the fortress where Kara and Mon-El are being kept prisoner, Winn stayed at the portal to keep it open, there he was attacked by a Maaldorian whom he managed to defeat.

A cloud of gas appears ready to take out Winn and the agents but Kara as Supergirl arrived to inhale the gas and disperse it into the air. Winn then offered to man the phones, though he had to leave, as he was texted by Siobhan who asked him to meet her at Noonan's.