I had high hopes for the Pirates when they hired Neal Huntington in the late 2000s. Huntington was a guy who embraced sabermetrics openly.
It's hard to blame him entirely for the Pirates struggles.
Cole wasn't elite until he got to the Astros.
Taillon was hurt a lot in the minors.
Pedro Alvarez had power and was a patient hitter but he just couldn't make enough contact to stay in the bigs.
Tony Sanchez was a flop. Hey, those are the breaks. He was a great college player.
They drafted both Mark Appel and Nick Lodolo who didn't sign. Appel has been a disappointment even though he was recently called up.
And while Lodolo is currently hurt with the Reds, he's one of the brighter pitching prospects currently in the game.
Shane Baz might be Tampa's best pitcher. And they have Shane McLanahan so that ought to tell you something.
Point being, it's not like Huntington and the Pirates have been horrible at identifying talent. It's just been a couple of bad breaks, bad timing and a lack of money (or at least a commitment to spending at the ML level)
The Pirates don't even need Yankees money. If they had Detroit Tigers money they'd be Wild Card contenders.