beckdawg
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Actually by all accounts Hendry was, and is, a very good scout so I'm not sure he was a bad talent evaluater I think he was a bad talent compiler for lack of a better word. Part of it was that he liked the toolsy guys as you said and part of it is that, under his leadership, they did not have a standard for who they wanted to draft which actually a bit surprising because Andy McPhail had created that kind of a standard player model in Minnesota and Hendry began his GM stint under McPhail. My impression was though that McPhail by that time didn't his job in Chicago much but that's just a hunch. The Hendry regime also didn't have much use for the emerging advanced metrics so you ended up with a haphazard draft strategy where player conflicted with rather than complemented each other and were thrust into a disorganized developments system. Can you imagine what it would be like for a hitter to be taught one plate approach at low A, another in high A then his AA or AAA coaches tell him to go back to what he was taught in low A or even something else entirely. Add that to the fact that these weren't exactly well rounded players and you have an unmitigated disaster.
Honestly, I'd argue the biggest gaff of Hendry's tenure wasn't talent acquisition. It was more the development of that talent. Could be a chicken or the egg type situation but so many high round picks didn't amount to anything and you had guys like Josh Donaldson who are MVP caliber players who were dealt away. If you look at the present front office, who's been their "bust" as far as draft picks go? Pierce Johnson? He's the worst I can name off the top of my head and even then he's not bad.
If someone wants to make the case that Hendry favoring toolsy guys was more the problem because they are harder to develop, that's a valid idea. However, that sort of goes with the territory. Most teams employing that model hope to land 1 or 2 super stars and back fill with money in FA. Ultimately I'm more in the camp of low floor players but it can be a viable strategy and if you do find a couple of super star types it's a lot easier to add someone like Lackey or Zobrist on the cheap than it is to sign someone like David Price.
And to be clear, I think a lot of the development issue was with the ownership. You'll recall one of the first things the Ricketts spent money on was a brand new dominican facility followed shortly by the new one in mesa.