Really if we draw any conclusion from the Dombrowski Era trades, it's not that he frequently overpaid. But most of the prospects he dealt away are actually making MLB. Ty Buttrey, Shaun Anderson, Gershon Bautista, Steve Nogosek, Logan Allen, Dubon, Moncada, Kopech. I have faith Basabe will one day as well. Really the only flops he dealt away are Espinoza and Javier Guerra, and the latter is trying to reinvent himself as a pitcher with an alleged 98mph fastball.
Did he just know his own farm system that well? Or just give in for any player they asked for and not worry about it?