- "Guys, you know I’ve been thinking a lot about the Earth. We gotta leave it better than we found it"
Being a former roommate who returned shortly after Coach left, Winston finally comes back from playing basketball in Latvia, completely unaware of anything that has happened in the US for the past two years. In Clavado En Un Bar, it is revealed that Winston was the 9th guy on the bench for the 8th best team in Latvia and after being traded to the Kraslava City outdoor league suffered a humiliating leg injury that ended his basketball career.
On Winston's first night back at the loft, he goes out with Nick and Schmidt for some drinks and gets wasted. Jess makes him breakfast the next morning and not having met him before, she introduces herself by singing while he is massively hungover. The new roommate relationship gets off to an even rockier start when Jess breaks the TV with a basketball. Winston later helps Jess get her stuff back from Spencer, and when Spencer doesn't offer up Jess' jam shirt Winston joins the guys by putting on one of her hats (they do this to dare Spencer to take the hats off of them).
Winston used to occupy the largest room in the loft, which Schmidt took when he left. He managed to manipulate Schmidt in switching rooms by claiming Schmidt is the new 'top dog'. This offended Schmidt because he felt like it was all a joke, but they later reconciled and earned each other's respect. Winston won the large room back by pulling some reverse psychology on Schmidt by suggesting he keep the big room.
Winston later begins adjusting back to life in the US, and the first things he does is look for a job. He quickly realizes he struggles with small talk in interviews as he has not been keeping up with current events for the last 2 years. He gives himself a crash course on the internet, watching countless youtube videos, and movies. He also has no experience, and cannot make a complete resume (skills in basketball, and love for ducks, which isn't even true). He lands a temp job in Bells, but is quickly fired when he wastes mailing supplies in practicing "Eye of the Tiger." He gets a job as a part-time nanny for Schmidt's boss who has a son, Elvin.
In Normal he decides to quit his job as Elvin's caretaker and lands a position as an assistant for the bombastic sports radio host Joe Napoli at KQTO 87.4 FM. He eventually moves up to be producer of his own talk show from 2:35 to 5:35 a.m.
When Jess has twenty minutes to decide if she should give-up teaching and take a new job, Winston attempts to illustrate the importance of making decisions, only to realize that he has never made a true decision in regards to his own career. Following this epiphany he quits his radio job in spectacular fashion. Again unemployed, Winston asks Schmidt for help with his career search. Although Schmidt doesn’t think Winston would be any good in marketing he agrees to let Winston shadow him to see what he does as a marketing analyst. Winston enjoyed the analytical aspect of Schmidt's job but also realized that he would not want to be behind a desk, to which Cece suggests that he should consider a career in criminal justice.
Winston had a no-strings relationship with Shelby before he left for Latvia. Upon his return, he reaches out and meets up with Shelby, and acts like an ass. She tells him off and that she's not interested and that he doesn't care about her. Winston makes amends by showing Shelby that he wants a real chance at a relationship with her and they start dating. After a while together, Winston pulls away again only to realize that he's really in love with her.
They become 'nauseatingly cute', as the other roommates put it, for a while until they hit a rough patch and realize that they're not really working. They feel the relationship has faded and ended things. Afterwards, Winston goes through a period of mourning and doesn't date for a while.
Feeling stuck in a dry spell and unable to strike up a conversation with women, Winston happens upon Daisy at the bar, who agrees to coach him on talking to women. She comes back to the loft with the group to play True American and Winston kisses her. They start dating, but the relationship mostly seems to revolve around sex. After a while Winston discovers that Daisy is cheating on him and in the heat of the moment, he takes her cat, the now infamous Mr. Furguson.
Winston, trying to rebound from his breakup with Daisy and talk to other women, asks Nick to watch his cat, Mr. Furguson, while he goes out with some coworkers. This all goes awry when, dejected by his hilariously failed attempts to talk to about 16 women, he comes back to discover that Nick let the cat escape through an open window. Nick and Winston go searching for him and find him at Bertie's house, a frisky, red-headed bus driver and former shoe store manager who had "a few dark years" and sold Christian T-shirts. Nick takes Mr. Ferguson home, leaving him and Bertie to flirt and eventually have sex.
Winston and Nick grew up together in Chicago, with Winston considering Nick's unreliable father Walt as a father figure. Nick oftentimes pranked and bullied Winston when they were younger, and the two experienced a lot of adolescent rites of passage together. Before meeting Tran and Furguson, the two consider one another their best friend.
It's implied that Coach and Winston went to the same college, as they played basketball together in college and this is presumably how Coach got to know the other guys.
- Baby, look, I don't want space, okay? I don't want anyone to have space. I want to be standing right in front of you. I want the air that you breathe to be the air coming directly from out of my mouth. I want to be just passing air back and forth between each other until it's mostly carbon dioxide and then we both pass out and die
- – Winston to Shelby
- Look at me being so naughty
- – Winston having fruity drinks
- I burnt a lot of bridges today… stuff got weird, stuff got racial. I used a lot of swear words then got sexual.
- – Winston talking to the gang about quitting his radio job.
- Winston played pro-basketball in Latvia for two years.
- He's from Chicago and grew up with Nick Miller.
- Winston at one point decides to work on a puzzle and discovers he is terrible at it, mostly due to the fact that he is colorblind.
- Schmidt said that he's the third smartest in the apartment (after Schmidt and Jess).
- Considers himself a fast learner.
- Hilariously sings Wicked songs while driving.
- Believes that both werewolves and Santa Claus are real.
- He is afraid of the dark.
- The only main character to not appear in the Pilot.
- Loves fruity mixed drinks, however, gets really weird when he drinks them.
- Loves bubbles and bathtubs.
- Loves pranks but is terrible at them.
- He lost his virginity to a prostitute.
- He and Coach played basketball together in college.
- According to Coach, has tiny hands.
- He gets injured easily.
- His father left at a young age, and he considered Nick's father his pop pop.
- Winston is allergic to MSG. When he eats it, his jaw locks up.
- Winston is the owner of a cat after he found out that Daisy was cheating on him. He took Furguson the cat from her, and he considers Furguson one of his best friends.
- Winston is an L.A.P.D. cop. He graduated from the academy in spring 2015.