Terry Ryan retired from his post as General Manager for the Twins a couple years ago, and while Ryan didn't make every trade exactly right, neither did he very often go far wrong or do as poorly as the current manger, Bill Smith.
The Twins have forever tried to get over the hump with humpties, from Sidney Ponson, Joe Niekro (at the end of his career) and Rheal Cormier to Livan Hernandez, Adam Everett and Mike Lamb, this has ever been their lot. As a smaller market team, it's the nature of things, you rarely get to sign expensive players. It is a shame, though, that so very often, the players the Twins sign do not pan out. Only Don Baylor, Jack Morris, Mike Redmond Paul Molitor come to mind as a free agent whom they signed who produced anything like was hoped for. Whereas many, many players have not.
However, that's not really the problem, it would be nice if free agents produced, but the real killer is, for small market teams, players whom they trade, usually players about to become free agents, need to bring talent back to the small market team that trades them.
Last season, the Twins made two meaningful trades:
The first sent Johan Santana, the best pitcher in the organization's history since Bert Blylleven, to the New York Mets. For Santana, an A+ level free agent, the Twins got Carlos Gomez, Deolis Geurra, and two not too well regarded prospects. Gomez, after starting off hot, has cooled dramatically, makes defensive mistakes, and is showing himself to be what the scouts said, a fantastically fast player, with good defensive range, but who makes enormous base running mistakes, and who, unfortunately, cannot bat lead-off because he doesn't know how to draw a walk EVER. While the Twins weren't getting killed with high-calibre offers, clearly the offers MUST have been better than this someplace, but the Twins took the wrong one. Guerra has potential, but it's hard to know if it will EVER turn out. This trade is quickly becoming a bust, and when it's the best player you have to offer, that just cannot happen.
The second trade is a little more ambiguous. The Twins traded Matt Garza and Jason Bartlett to Tampa for Delmon Young and Brandon Harris. Young is hitting .294, Harris .251. However, Garza was a 24 year-old, hard throwing right-hander. His current ERA would tie him for second on the Twin's staff, and considering the generally better defensive team the Twins have over the Devil Rays, it's not unlikely Garza's ERA would be lower. He's given the 'Rays' quality starts time and again - and was not in any sort of free agent year. Bartlett, who struggled at the plate last season for the Twins, played a position where fielding well is more important than hitting well, and Bartlett was an excellent fielder. This year, he's hitting better, considering he was 25 when traded, we gave up on him too soon. Considering Adam Everett is hitting .189, and Harris can't play second base that well, and is pretty awful at short - this was a horrible trade, on a one for one basis, Bartlett is just flat-out a better SS. Delmon Young hits .294, but he's been awful in the clutch, is a lousy-armed and poor ranged left-fielder who hits for NO power. That's totally, utterly unacceptable. Some positions can be slap hitters, if you have power elsewhere, LF CAN be, but shouldn't, but Young was brought in to keep pitchers and teams honest, by hitting between Mauer and Mourneau, and he can't do it. The Twins moved him out of that spot because he's not reliable enough as a hitter, and isn't fearsome enough with power. Beyond that, his average is likely inflated by hitting behind Mourneau. He's been a C- grade player at best, considering the Twins gave up Garza to get him, this was a horrid, awful trade.
The real problem goes a bit deeper too, it's not as if the Twins didn't have solutions at second and CF in their minors. Denard Span and Alexie Casilla have proven they deserve to play. The Twins would be FAR better off with Bartlett and Casilla up the middle, Span in CF, and Garza in the rotation, having spent the money they spent on Livan Hernandez to get a DH or LF (or 3b) who could hit. Punto has returned to hitting, and is an excellent 3b, and good enough SS to play - but you didn't know that would happen. Finding a decent hitting DH really, REALLY isn't that hard, and they could have played Kubel in LF, Cuddyer in RF, Span in CF, and been a much better team. The trade of Santana CERTAINLY should have brought a starting player or high-grade pitching prospect, and as it turns out now, it sure looks to have not done so. Gomez at least could be kept for his utility and speed (though not as a PH, he can't find a pitch he won't swing at), but Monroe should be jetisoned, as should Mike Lamb, to make room for Liriano, to keep Span in the majors, and to have room for Cuddyer.
The crying shame is both of those trades were much easier to see as a bad move when they happened, but worse, that the organization didn't see it had good options in the minors for what it got for Garza and Bartlett, and look to solve glaring problems at 3B and LF with the Santana, rather than solving CF - bespeaks a General Manager and minor league evaluators who didn't do their jobs right, not even close to right, last year. While the Yankees or Red Sox can recover from that kind of screw-up, smaller market teams, like the Twins, rarely do. The proof will not be this season, but maybe next or the year after, when they need Garza, and still don't have a quality player at 3b or SS (depending on where Punto plays). They got killed twice last year - one more than a team like the Twins can afford.