I think the major reason I no longer harbor any particular distaste toward the Yankees — besides a general preference for underdogs — is that I’m no longer in high school and so no longer need to regularly interact with people like this guy:
The Yankee fans I deal with now tend to be people more like Alex Belth, a guy reasonable enough to recognize that he is lucky to root for a team with the resources to contend every year, who does so without the obnoxious sense of entitlement too frequently demonstrated by people like the fellow seen here.
I know plenty of Yankee fans like that and I suspect they might actually make up more of the actual fanbase than we assume; we merely associate Yankee fandom with people like this guy because of confirmation bias, and because they express their allegiance in a much more vocal and detestable fashion than the Yankee fans smart enough to realize that not everyone gets to root for a perpetual winner.
That GIF (taken from Scratchbomb) is mesmerizing. I could watch this guy for hours.