Well, those are the facts, though I'm not sure the strategy was one-dimensional. He didn't expect to bat 1000 (or even .500) on a bunch of over-30 players (and Hellickson). The best-case scenario is the flips, the worst-case scenario is the injuries. The middle scenario is the guys actually playing for the team and not being under contract next year, even if they lose them for nothing, while also buying time for prospects who weren't ready. And that's what's mostly happened.
Because what was the alternative to Kendrick, or Buchholtz? Guys who cost more money. Guys who would rate a multi-year contract. Even older or more injury-prone guys. Or the type of players they had last year (Lough, Bourjos, Hunter) or inferior players like on past pitching staffs (Jerome Williams). Hindsight certainly says that with Altherr and Nava they didn't need two veteran corner OFs, but the time those OF signings bought Williams seems to have paid off. And I don't know that you can argue it was bad to keep Hellickson and get Buchholtz given the state of the rotation.
If Klentak fails to get much this deadline it will be because he doesn't have very good players, and yeah, he's accountable for botching that aspect of it (particularly with Saunders given his salary and contract option, and with Hellickson too).But I think it will be more about that than his temperament for or ability to wheel and deal.