New Girl followed the quirky Jessica as she tried to rebuild her life after ending a long-term relationship and moved into a new loft with new roommates who end up becoming a big part of her life. One of those roommates was Winston Bishop.
Winston was a lovable and unique character who slowly developed in the show as his hobbies and interests, like cats and pulling pranks and his brightly colored wardrobe, were revealed. Although Winston was a lovable and caring character, he still did some terrible things. Here are some of the worst things Winston did throughout the show.
Being The Only Winston
For most of the series, Schmidt goes by his last name and his first name is a mystery.
At the end of the show, Schmidt finally reveals that his first name is actually Winston but he never used it because the loft couldn't have two Winstons. Winston refuses to give Schmidt the name back because it's his identity.
Overshadowing Jess
Jess brings home a group of at-risk teens who she tries to help through the power of music, specifically handbells. Winston picks them up and is immediately talented with the instruments and takes over Jess' instructing with disastrous results.
It was a selfish move as he only cared about being good at something instead of caring about what Jess was trying to achieve by caring for and supporting these kids.
Saying Schmidt Is A Romney
After talking about how much Schmidt looks like he's part of politician Mitt Romney's family, Winston comes up with an idea to get both of them in a club. After getting into the club, women approach Schmidt and hit on him thinking he's part of the Romney family.
Winston goes along with the scheme, letting Schmidt lie to the women, and gets CeCe out of the way so she doesn't let anyone know he's not.
Pranking CeCe's Wedding
CeCe was about to marry Shivrang, but Schmidt feels like she secretly doesn't want to go through with it but is too afraid to cancel it and disappoint her family.
Schmidt enlists Winston to prank the wedding and ruin it so CeCe has an out if she doesn't have to marry him. Although the plan works, Winston's over the top Prank Sinatra persona still ruins the day.
Telling Schmidt To Buy Drugs
To be fair, this is completely on Schmidt as he worries that Winston might not be able to be his authentic self living with all white roommates. Winston uses the opportunity to mess with him as Schmidt shows his ignorance and stereotypical views of African Americans.
Winston sarcastically says he misses smoking crack and sees how far he can push Schmidt. It's a good and funny prank that hopefully teaches Schmidt a lesson, but it may have gone a little too far.
Being Careless About The Police Exam
Winston learns that he failed the police exam the first time he took it and has a bit of a break down because of it. After trying to apply to a coffee shop, he's told he didn't fill out the back of the application form and wonders if he did the same on the police exam.
He and Coach go to talk to an officer and he says the exam is administered through a computer. Winston wants to be a police officer so bad but he is pretty careless about the process.
Getting Prank Married
Winston briefly dated Rhonda (Sonequa Martin-Green) and his friends quickly found out that she had the same prank issues as Winston does as she pulls extreme and sometimes dangerous pranks.
At the same time, Winston is trying to reckon for his possible romantic feelings for his partner at work, but he agrees to the hilarious "prank" of legally getting married to Rhonda.
Making Schmidt Drop His Gift
Schmidt tells Winston that he's going to give CeCe jewelry when they all join Jess and Nick on a cruise they had planned before they broke up.
Schmidt is about to give CeCe the gift as she's standing by the railing of the side of the ship. Winston decides to run up to Schmidt and tickle him and Schmidt throws the jewelry box over into the ocean.
Trying To Convince Nick His Girlfriend Is Homeless
Nick starts going out with his friend Tran's granddaughter and Winston is utterly convinced that she is homeless. As he's going through the police academy training, he puts a profile together and tries to convince Nick that she is homeless.
Nick doesn't believe him and either way, Nick cares about her so he isn't bothered if she is homeless, and Winston turns out to be wrong about her living situation.
Telling Jess That CeCe Likes Nick
Although this was to cover CeCe's secret crush on Schmidt, Winston still let Jess believe that CeCe liked Nick.
Winston tries to comfort Jess and keep CeCe's secret, but he keeps the lie alive and it all ends with disastrous results. Jess tries to talk to Nick about it and Winston doesn't do anything to stop the miscommunication and the lie messes with Jess.