He was played by Jeremy Jordan, who also voices Varian on Tangled: the Series.
Winn was born and raised in Newark, New Jersey. During his childhood, he was very close to his father, Winslow Schott Sr., and the two would often go to the latter's workshop and build toys. After Chester Dunholtz stole Winslow's toy designs, Winslow sent a teddy bear with a bomb in it to Dunholtz, killing six people. At 11 years old, Winn had to watch his dad be dragged off to prison and his crimes exposed which earned him the nickname "Toyman". At some point after this, his mother ran off for reasons unclear. After this Winn was then put into the foster system. To avoid the scrutiny of being labelled the son of Toyman, Winn didn't reveal his relation to his father to anyone he knew.
Later in his life, Winn became employed at CatCo. He first met Kara Danvers when she came in to interview for the position of Cat Grant's assistant, wishing her good luck. He believed in the existence of aliens other than Superman, citing an armored car robber who reportedly had horns, and maintained a web site documenting alien sightings. He has feelings for Kara and has unsuccessfully attempted on several occasions to ask her out or tell her about them. In many ways an archetypal IT geek, Winn nevertheless doesn't believe that everything in life can be modeled by algorithms.
After the rescue of Flight 237, Kara confided in Winn that she was the woman who saved the plane. Winn was skeptical until Kara showed him her powers, and then enthusiastically assisted her, helping to design her costume and alerting her to several crimes and disasters. 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 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. He worked with James to advise Kara while she responding to a number of lesser emergencies from Kara's apartment, for which Kara was thankful.
Winn later converted an abandoned office in the CatCo building into a secret base of operations, showing it to Kara and James. They first used it to discuss their plans to defeat Reactron. When James carelessly refers "Clark", Winn quickly works out that Clark Kent is Superman. That night at Cat's launch party, Winn covered for Kara's late arrival, asking her to dance in lieu of any reward — though James cuts in when he arrives. During Reactron's attack Winn was almost crushed by a falling support beam, but was saved by Kara.
When Cat receives an award and Kara offers to watch her son Carter so she can attend the ceremony, Winn is roped into taking after him when she has to leave the office as Supergirl to deal with a number of suspicious attacks on Lord Technologies. Winn unexpectedly gets along very well with Carter, finding they have much in common, but is distraught when Carter sneaks off to the launch of Maxwell Lord's new superfast train in the hopes of meeting Supergirl. He calls Kara and she trusts him over D.E.O. reports of a bomb at the airport, heading to the train and saving everyone aboard except the bomber. 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.
At Thanksgiving, Winn reveals he has no plans, and cautiously accepts Kara's invitation to share the holiday with her family, meeting Eliza Danvers for the first time. He leaves after Alex and Eliza have a fight over Alex's work with the D.E.O. Kara later apologizes for the family drama by giving Winn some leftovers, and he reveals that his lack of plans is because his father is deservedly in prison. He kisses Kara on the cheek, but they are interrupted by the arrival of James and Lucy.
Growing more suspicious of Hank, Alex tells Winn that her father Jeremiah was killed while on an assignment working for the D.E.O., and asks him to hack into their servers to see what he can find out. Winn reluctantly agrees. He also joins James in advising Kara that she doesn't have to fight the Red Tornado, but she wants to prove to General Lane she and her cousin can be trusted. He is less than thrilled when Kara reveals James is bringing Lucy to games night; their closeness in a game of Taboo makes Kara even more jealous of Lucy's relationship with James. Later Winn meets with Alex and Kara to reveal that Jeremiah was one of two agents who went missing, presumed dead, while tracking down an alien in South America. The other agent later reappeared - it was Hank, who has been tampering with Jeremiah's files ever since.
When an earthquake hits while Kara is without her powers, Winn helps restore telecommunications to the CatCo offices, earning the notice of Cat, who asks him to hook up a live feed so she can send a positive message of hope to the city. He also walks in on James and Kara sharing a hug and assumes it is romantic, making him even more jealous of James and disappointed in Kara. 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. Though initially it seems there's nothing too scandalous, Winn eventually finds a series of mysterious payments to Adam Foster, a young man in Opal City. 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 CatCo board. After spending time together with both of them, James recognizes Winn's feelings for Kara and tells him to take a risk and tell her how he feels.
Winn is later informed by Kara that Cat believes her to be Supergirl. Winn later confronts James for lying to Kara about not having a lead on what Maxwell Lord was hiding. 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. The trio later agree to stop Maxwell together.
Son of Toyman
Winn is left a doll on his desk from his father, Winslow Schott Sr., who had broken out of prison. Later when Agent Cameron Chase arrives asking about his father's whereabouts, Winn denies knowing anything, though after talking to Kara, shows Agent Chase the doll, which tells Winn to meet him at their "favorite place". 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. 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 later surmises that his father must be hiding in an abandoned factory that he use to own, causing Kara to fly off in an attempt to capture him.
At Kara's apartment, Winn attempts to kiss Kara though he is rejected by Kara, and leaves upset. While leaving, Winn is then kidnapped by Winslow Sr. and is taken to a warehouse. He reveals that his whole plan is for Winn to kill his former boss, Chester Dunholz so that they can be together in prison. To ensure his compliance Winslow Sr. says that he has hidden ten bombs in random toys at the convention and he will set them off if Winn does not go through with it. At the National City Toy Con, Chester Dunholz, makes his speech, and Winn arrived with the weapon disguised as a plastic gun. As Winn fired the gun into the air, Cameron and the FBI agents shoot to kill him, but Supergirl protects him, also protecting the crowd from the bombs. The next day at CatCo, Winn receives an apology from Kara, and apologizes to her for kissing her, though he isn't sure where they stood after the ordeal he went through.
Moving on from Kara
When Kara attempts to talk to him as she passes him by, Winn shuts down the conversation, though he tells her to have a nice day. Later, when the same thing happens though Kara is silent, Winn remarks that she is awfully quiet. Upon hearing the latest news about Supergirl tossing a car hanging off a bridge, Winn is told by Kara that the woman in the news is a doppelgänger. He did some digging and found out that there were seven comatose Jane Does brought to Prometheus Genetics, owned by Maxwell Lord. He and James later shared a drink over their romantic troubles.
Winn, along with James and Alex discovered Kara on the floor of her apartment with an creature attached to her. Winn and James were later ordered out of the D.E.O. by Hank Henshaw. 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. They were then taken back to the D.E.O. by Alex, and later calmed Alex down when she thought she had been pulled out when she went into the hallucination to save Kara. He later informed everyone that he had found some hidden transmissions that used Lord-based servers based on the same lab the Kryptonians attacked before, and they left a virus that allowed them to override normal control. Winn later waited with James and Alex at Kara's apartment, making up with Kara when she arrived, with the two giving each other a high-five. Winn was present when Cat announced her new assistant to Kara, Siobhan Smythe. He later observed a hostile exchange between the two, through their computers.
Winn is later ordered by Cat to fix her systems, when a hacker appears on her monitors. At Kara's apartment, Winn tried to hack the hacker's code, though to no avail when the hacker appeared on the screen. The hacker then came through the computer, though she soon retreated after Hank and Alex arrived. Back at CatCo, Winn offered to help Siobhan make copies, but she was upset over finding that her father was listed as a member of a cheating website thanks to Indigo and leaves Winn to make the copies. Later at D.E.O., Winn attempted to track Indigo, trying to decipher the Kryptonese text, and eventually discovering Indigo's plans to destroy National City using nuclear missiles. Winn later attempts to infect Indigo with a virus that will disable her, though she teleports her arm through a phone screen and begins choking him. However Winn is able to put the virus into effect, disabling her. At CatCo, Winn tells Siobhan about his family and how he has felt just like her, causing her to kiss him.
Winn is later discovered by Kara, making out with Siobhan in the storeroom. The next day, he is surprised to see Kara use Cat's elevator. He is later present as Siobhan is fired, and attempts to comfort her, though unsuccessfully. Winn and James are invited by Kara to the club, and while waiting for her, Winn talked to James about Siobhan. Winn and James later alert Hank and Alex about the changes in Kara.
When Cat called for Kara, Winn had to remind her that Kara was out sick for the day. 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. 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. Cat later has Winn analyze the email Kara supposedly sent, discovering that the typing pattern didn't match Kara but instead matched Siobhan. Winn later finds a severely drunk Siobhan on the roof of a nearby building, who is furious at Winn for turning on her, though he tells her that her behavior won't get her anywhere. One of Siobhan's spike heels breaks, causing her to lose her balance and stumble off the roof. She screams in terror, but just as she is about to fall to her death, the sound waves from her screams break her fall and blow a hole in the concrete, while an equally stunned Winn watches.
Winn and Kara took Siobhan to the D.E.O. for examination after her fall from the roof. He promises to stand with her after the events that had transpired. He is later present when Siobhan arrives at CatCo, pushing past him, and using her sonic scream to knock Kara off of the building. He is later introduced to Barry Allen, a speedster from another universe, who explains the multiverse concept to him, Kara, and James, and brings them all ice cream. Afterwards, Winn excuses James of being jealous of Barry. At the D.E.O., Winn and Barry both agree that they should build a trap to subdue Livewire and Siobhan, though Kara objects against it. 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.
Winn along with the rest of National City is later put under the control of Myriad. 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. The two then tell Kara to accept defeat or die. Winn is later snapped out of the mind control by Supergirl's speech to National City, with several flashbacks of Supergirl coming back to him. The next day, both him and James apologized for their actions, and Winn excused himself when he realized that Kara and James needed to talk about something that had nothing to do with him. He later noticed Kara's look of distraught, and asked her if she wanted in on the lunch order, though she rejected his offer, but thanked him for always being a good friend to her. Winn later experienced excruciating pain as the Myriad frequency increased, though it was stopped by Supergirl. He was later present at Kara's apartment during the celebratory dinner they were having. 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.
Joining the DEO
After some time, Winn decided to change his profession and after having proved his valor was formally welcomed in the D.E.O. by J'onn J'onzz. When Supergirl and Superman faced Metallo, he fashioned them Anti-Kryptonite Devices that temporarily helped them to fight the Kryptonite-powered cyborgs at full force. Later, Winn helped to track the escaped Mon-El, after he is suspected by Kara and the D.E.O. to be the President's attempted killer. When Mon-El is clear of all charges J'onn decided he has to stay at the D.E.O., as long as they do not understand the full potential of his powers and Winn was delegate to keep an eye on him. It turned out that Mon-El has no powers other than super-strength at a less level than that of Kara, and super-jumping. Thereafter Mon-El managed to persuade Winn to withdraw him from the D.E.O., to test his ability, despite the ban of J'onn. However, they went to the bar and get drunk. 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. The next day, J'onn told Winn that he knows that he and Mon-El went to a bar the previous day.
After Winn saw James on the security camera recordings during the attack on the Federal Reserve Bank by a criminal gang armed whit alien weapons, he came to his office at CatCo and asked him what he was thinking, to which James replied that he hid behind his camera for too long when his friends became heroes and save people, and that his vocation is to do the same, so he asked Winn to make him a suit and weapons. However, Winn refused, because he believes that he's just going to get killed. Later, Winn and Kara arrived at Lena Luthor's charity evening. After some time a gang of criminals broke at the party starting a struggle with Supergirl, Winn hides under one of the tables, where he met Lena, who tried to establish a black burst generator, which would cut down their weapons. Together they were able to fix the device, destroying the criminals' weapons so that the gang would be captured.
The next day, Winn came back to James in CatCo and told he would help him, and that he already has a suit in development, then he asked James "not to throw the bullets" until he will finish the costume.
When James learned that Kara has suffered from Parasite's hands, he demanded Winn to give him the suit, but he said that the suit is not ready yet and that if he used it right now he will probably die. James was forced to agree but, later, when Kara was completely drained of her powers by Parasite, Winn said James that they can not wait any longer, and, after he made sure that James is confident in its decision, he showed him his new suit. Later, Winn, sitting in a van and watching the situation, helped James to fight Parasite.
The next day he came to CatCo and congratulated James on the successful start of his heroic life. Then he asked if it is really worth to hide it all from Kara to which James replied that it is better to hide it, or she will stop 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. After Winn saw in the news that Detective Maggie Sawyer reported that she gained a warrant for the arrest of the Guardian, Alex comes to him and he confesses her the truth, so she agree not to tell Kara and asked Maggie to stop the hunt of the Guardian. The next day James and Winn discovered the impostor was targeting criminals who cheated the system, as both victims had convictions that were passed over because of technicalities. He also told him of another man who'd killed a woman named Julie Karnowsky, only to be let go because of insufficient evidence, whose husband Phillip was a former Navy SEAL who'd gone missing months ago; they come to the conclusion that Phillip was the impostor and managed to stop him. Later James, Winn and Alex celebrated Kara and Mon-El's escape from Cadmus, where Mon-El inquired to them on the specifics of human relationships.
During the Thanksgiving dinner at Kara's apartment, James and Winn planned to tell her about their activities but are stopped first by Alex's vain attempt to come out to her mother and then by the opening of a breach. Some nights later, while he was fighting crime alongside Guardian, one of the criminal they were chasing run in his direction and, as he exited the van in an attempt to stop him, Winn was quickly subdued and nearly killed by the robber if not for Guardian's intervention. The accident leaves him a little shaken and with a fear of dying, despite at first he tried to deny it and says everything was fine; however, after the D.E.O. found out that Kara and Mon-El had been taken to the planet Maaldoria, where they wouldn't have their powers, J'onn ordered him to accompany Alex in a rescue mission and Winn broke out revealing Alex about his fears, she reassured him that what he feels is normal convincing him to join her strike team.
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. After they returned all to Earth, Winn went to James' office enthusiastically telling him about his adventure on space.
After one of their usual night patrol, Winn and James saw that the latter was hurt as the suit hadn't protected him fully which made Winn a little hysterical as he had to fix it on top of making Mon-El a suit. James was surprised that Mon-El actually wanted to be a superhero but Winn told him that he had enough with the secrets and that they should tell Kara but James was adamantly against it. However, seeing Winn becoming so shaken up after their close calls, he thought that it might be time to tell Kara the truth. However Kara found out the truth about Guardian's real identity on her own and got extremely angry at both James and Winn. 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. 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. However, they claimed they will not stop.
Initially, Winn was introduced as tech-savvy IT guy who is Kara's best friend, whom he has romantic feelings for. He is loyal to Kara and her cause, helping Kara create her Supergirl uniform and providing them a secluded workspace to monitor criminal activity in National City, however he was disappointed when James found out her secret identity as well. His creative thinking and technical skills has allowed him to think of solutions no one else has thought of, such as deducing Non's plan involving Lord Technologies satellites, uploading malware into Indigo and re-engineering protective armour for Kara and Clark Kent. His skills also earned him his spot in the DEO.
He is the jealous type when it comes to Kara, especially with her relationship with James. When he made his feelings known, he was deeply hurt that Kara did not feel the same way, but he eventually came around out of sense of friendship and loyalty and having dating Siobhan, he has moved on from Kara and the two are once again best friends.
Family is a sore subject for him, as he is incredibly angry with his father for his crimes and fears one day he will become like him. He was also angry with his mother for years for abandoning him, until their reunion over twenty years later, when he learns that she was forced to leave him and cut off from communicating with him. They reconciled after that.
- High-level intellect: Winn is very intelligent, as he is able to think of solutions no-one else has thought of; such as deducing Non's plan involving Lord Technologies satellites.
- Computer specialist: Winn is a highly skilled computer specialist; as he was able to uploading malware into Indigo.
- Expert computer hacker: Winn is a highly skilled computer hacker, capable of breaking into any computer system, which makes him a valuable asset to both the D.E.O. and Supergirl's team.
- Expert engineer: Winn is a highly skilled engineer like Cisco on Earth One; as he was to create two anti-Kryptonite suits for Superman and Supergirl, to protect them from the effects of Metallo and Dr. Gilcrist's Green Kryptonite beams; despite it being a rush job. He was even able to create a protective suit for James Olsen, after the latter told him about wanting to become a vigilante; albeit Winn was initially reluctant to help James.