To me, he's done worse in this "fringy" area than I expected. For every Wacha, Hill, Duvall and Strahm, there are 2 Richards, Perez (twice), Kluber, Kike II and Diekmans.
He's big on a few low cost guys like Schreiber, Refsnyder, Bernardino, Arroyo, Reyes, McGuire and others, but the long list of failures on those types of deals is scary, too, especially with RP'ers.
His biggest signings look to be his worst, so that makes the lesser ones look better, I guess.
Story
Yoshida
Richards
Kluber
Although Jansen at $8M x 2 looks good, if you call that "big."