I don't think this is necessarily accurate. I think it's more that he constantly pursues the wrong free agents. If you're not going to spend big, go for risk/reward guys with upside, not proven mediocrities who fall into the same pitch-to-contact category as what you already have. There were plenty of guys who signed for a similar amount (or less) to Correia/Pelfrey last year that would've made a lot more sense.
OK, here are most of the pitchers that were in that group. I might have missed one or two. John Lannan? Anyhow, other than Feldman and Correia, not a lot was gotten in that price range. I think the Cubs signed Villanueva to a similar deal but he spent most of the time in the bullpen (although I know some Twins fans talked him up). Anyhow, which high risk/reward guys was I missing? I guess Liriano?
Scott Feldman - Cubs - 1/6m, 12-12 105 ERA+, 181.2ip, 1.6 WAR
Kevin Correia 2/10m 9-13, 97 ERA+, 185.1ip, 1.6 WAR
Brandon McCarthy - DBacks - 2/15.5m - 5-11 84 ERA+, 135ip -0.2 WAR
Dan Haren - Nats - 1/13m - 10-14 81 ERA+, 169.2ip -0.1 WAR
Ryan Dempster - Bos -2/26.5m 8-9 89 ERA+, 171.1ip, -0.2 WAR
Joe Saunders - Seattle - 1/6.5m - 11-16, 70 ERA+, 183ip -0.3 WAR
Mike Pelfrey 1/4m 5-13, 78 ERA+, 152.2ip, -0.3 WAR
Shawn Marcum - Mets - 1/4m - 1-10 67 ERA+, 78.1ip -1.0 WAR
Joe Blanton Angels - 2/15m - 2-14 62 ERA+, 132.2ip -2.0 WAR
Scott Baker - Cubs - 1/5.5m 3 starts, 15ip. Missed most season w/injury
(This is bWAR but fWAR can be very different - according to them, Pelfrey was a 2 WAR pitcher this year).