The only other times the GOP won NYC were 1896 and 1920.
They won it in 1896, but not 1900 or 1904? That seems...strange.
Bryan's 1896 bimetalist populism campaign failed spectacularly in the Northeast. Once the focus turned to other issues (imperialism, tariffs), the Democrats bounced back a bit there.
Yeah, I can see where Bryan would be the kind of Democrat who wouldn't do well in NYC, but I'm just surprised he carried it in 1900 and 1908 but not in 1896 when his margin of defeat nationally was smaller. As you said though, different issues.