Rewatching New Girl and I love Winston but the show really made him kind of sad and a bit pathetic later. He starts off as this cool retired basketball player, who's trying to grow up and become more mature since he's no longer a star athletete and isn't given everything anymore.

And a lot of his early storylines involved him being the confident/cool character and learning to put up with the nonsense of the gang. But as the show went on they basically crushed his self confidence, made him basically beg girls to date him, become a crazy cat person, and always making mistakes or failing (at least they made him a decent cop though).

I just realized in the episode "Spiderhunt" when they laugh at the idea of Cece ever being into him, even he laughed at how unconvincing a lie that is. And it's a bit weird bc I feel like Cece could have easily been into early seasons Winston if she didn't have a storyline with Schmidt.

They even retconed his basketball career in Latvia, when he was a star player who hurt his knee and had to retire to a joke who didn't get off the bench and then hurt his knee playing in a joke league that plays on grass on a hill. In the beginning he was clearly shown to have been a legitmate star athletete (or at least enough to play somewhere professionally even if not in the NBA).

Kind of bothered me the first time I watched the series and now it bothers me again. Maybe it was due to him originally being a replacement for Coach but then they changed his character into his own, but I feel like our boy deserved better than being the apartment sad sack.