If there was ever someone who I wanted to head my organization in the first years of a complete and total rebuild, it's Ben Cherrington. That guy has a tremendous eye for talent; not only in his organization and others but at the college and high school level too.
I bet that Pittsburgh is a monster in three or four years.
2012, Devin Marrero (24th), Brian Johnson (31st), Pat Light (37th)
2013, Trey Ball (7th)
2014, Michael Chavis (26th), Michael Kopech (33rd)
2015, Andrew Benintendi (7th)
2016, Jay Groome (12th)
To be fair, he signed Devers and Darwinzon in 2013-4, so I'm willing to credit him that. And a year later Moncada and, unfortunately, Castillio.
In terms of MLB trades for players or prospects, there was the Punto trade - glorious in terms of cash for subsequent free agents, but we really didn't get a single good player out of it. There were more workman like trades of Boston prospects for Porcello and Miley and Kimbrel and Sale, and shipping out various vets at trade deadlines. If we're on that particular bus though, we did send a lot of value out of the org for players like Carson Smith and Tyler Thornberg. I'm not saying those were bad trades at the moment, and luck is a factor. But it's not like the results of trading for major leaguers were unmixed.
Looking at the trades from late 2011 to 2016, I really don't see one where a significant "under the radar" younger minor league player was acquired - which you'd think would be the case if he had a lot of talent insight. Two exceptions might be
Miller for E-Rod trade in 2014. . .but IIRC E-Rod was highly regarded at the time. And cash for Sandy Leon in 2015 - that turned out great, so I'll spot him that one as a talent spot.
What Cherrington *did* do was hold onto the 2011 draft class, and not trade off many excellent players. (Barnes, JBJ, Betts, Shaw) That's a skill, and he should get credit for that.
His FA signings were a mixed bag - 2013 was an absolutely great pick up of FAs for good prices. But then, Castillo, Sandoval, H-Ram, Price. . .those did not work out well.
Overall, I'm just not seeing
tremendousness here. Devers and Moncada are great gets, but if he had an eye for talent, I'd honestly expect more eventual ML over 4 years. Sure, propsects are lottery tickets and all that, but. . .there's not a ton there.