He is portrayed by Henry Czerny.
Winslow eventually had a son, Winn. During the time Winn was young, his father was a good parent. Together, they would often go to his workshop and build toys. After his boss stole his toy designs and grew rich of them, Toyman stuffed a bomb inside a teddy bear and sent it to his boss. The man's assistant opened the package however, setting off the bomb, accidentally killing herself and five other people. For this, Winslow was arested and imprisoned at Van Kull Maximum Security Prison and gained the nickname Toyman as a result of his actions. Winn grew to despise his father.
Over a decade later, Winslow broke out of the prison, killing three of the guards with a bladed yo-yo. After escaping he sends his son a clockwork toy on which a message for Winn is recorded. The message tells Winn to meet his father at "their favourite place". Winn however tells this to the FBI agent who plans to use Winn as a trap to lure in Toyman. Winn waits for his father at a toy workshop at an arcade near a yacht harbor. Inside he finds another doll and is recorded by the eyes of another. He eventually meets Winslow who tells him that he broke out of prison for him. He calls Winn his "greatest work", claiming that together they could achieve everything.
The FBI then enters the building, ordering Winslow to surrender. When Winslow doesn't move, only asking his son how he could betray him, the agents open fire but it is revealed that Winslow wasn't in the room, merely projecting himself onto a glass wall which shatters under the gunfire. The puppet on the floor then tells Winn that he told him to come alone and that Winn better starts running. Gas then streams out of several toy elephants, slowly suffocating Winn and the agents. Supergirl breaks through the roof and breathes in all the gas, saving the agents from certain death. She then flies up high into the sky to release the gas far over the city.
Winn eventually finds out where his father could be hiding and, to capture him before the FBI can kill him, asks Supergirl to go there. However, in the factury Winslow sets a trap for Supergirl and traps her in a box full of quicksand. He also reveals that he kidnapped a small child, trapping her in a box which is transported through the facility on a conveyor belt. Supergirl freezes the quicksand with her icy breath and catches the box before it can fall to the ground but it is revealed that the box only contains another clockwork doll. The same night, Winslow kidnaps his son right outside Kara's apartment.
He brings Winn to his hideout and reveals to him that he broke out of prison to get revenge on his former boss Chester Dunholtz, blaming him for seperating him from his son. He tells Winn that not he, but Winn will be the one to kill the man. He tells Winn that he has created a special toy gun for Winn which Winn can smuggle inside the building where Dunholtz will be receiving an award. Knowing that Winn would never do something like that willingly, he reveals that he planted ten bombs in ten random toys at the convention and threatens to blow them all up should Winn not kill Dunholtz. He also states that no matter whether they succeed or fail, he and Winn will end up together either in prison or in death. Winn arrives at the convention, enters the stage but is unable to kill Dunholtz. Supergirl arrives in time to shield Winn from the FBI agents who shoot at him. Winn reveals that bombs are in the building to Kara, who scans the room with her x-ray vision. She realises that Winslow is in the basement and about to trigger the explosives. To save the people Kara destroys a waterpipe and freezes the water, creating a wall of ice to shield the civillians from the blast. After the bombs go off, Kara tracks down Winslow and delivers him to the police. Winslow is returned to prison.