Laugh all you want, but you don't get to 27 rings without playing in a lot of World Series.
Yes, the playoff format used to be different, especially in the way where it did not exist until 1969. But that didn't prevent the Yankees from out-scouting, outmaneuvering, and outgunning all comers for the better part of four decades prior to the introduction of the League Championship Series. Perhaps, if things had been different, we would have some old cracklin' radio debates about how the 1927 Yankees were killed by a long layoff and never should've lost to the Tigers. Knowing the Greatest Generation, though, they probably would've just grinned, bared it and admitted they should've been tougher.
It certainly got more difficult to advance to the World Series and emerge victorious once MLB's head honchos added extra playoff rounds, but that didn't make the Yankees any worse at it. The reason this fan base is called "entitled" is ... well, their current 14-year stretch between championships/World Series appearances ranks among the longest in franchise history.
Longest World Series Championship Drought in Yankees History
Not coincidentally, the Yankees' longest stretch without winning the World Series was the first 20 years of their existence. On a technicality, though, they were the New York Highlanders until 1913, meaning they only went 10 years as the Yankees before winning their initial title (and eight years before making the Fall Classic).
Following their first championship, the longest they've ever gone without winning a title was the gap between 1978 and 1996, 18 agonizing years that featured only three postseason berths. Next October, the current Yankees will reach the 15-year mark.
What's the longest the Yankees have ever gone without winning the American League and playing in the World Series?
That would be the 1981-1996 portion of the previously mentioned gap, meaning the modern Yankees have already matched that. If they make the World Series in 2024, it'll be a tie. If they don't, they're the worst in franchise history.
No pressure on Aaron Judge's captaincy. Certainly.
Ironically, it's the playoff format that might save these Yankees. It's unlikely they'll wind up with the best record in the American League next season, but they could always knife through the playoffs if they qualify. Back in the day, the lack of short series ensured the Yankees earned an automatic ticket to the Fall Classic. Nowadays? They're more likely to fight through the bracket rather than nab the top seed.
Hopefully, no matter what hurdles lie in their way, the 2024 Yankees find some way to avoid making franchise history in the worst way next fall.