This just shows, imo, what an awful job they did drafting and developing the end of Ryan's first term....and no, I'm not blaming RYAN, I'm talking about the entire organization there.
Willingham, imo, isn't hindsight. Many pushed for him to be dealt, and I recall reading on mlbtraderumors that the Twins wouldn't because "we aren't a farm team for others teams" or something like that. Or maybe I dreamed that, but I think not....
Perkins was a classic no brainer move, they didn't make. I still have no idea why.
Perkins was (along with Mauer) the face of the Twins at the time. They'd just moved into a new stadium and his was an incredibly team-friendly contract. I think they didn't want to trade a guy like him. I think it's dumb (his contract and performance at the time represent the only really elite trade target the Twins have had) but I imagine those played a factor. Sucks that they didn't.
Willingham is more complicated. I always had the impression that the "farm team for others" thing was more the public comment after the Twins found a lukewarm market for Willingham. He hit a ton of homers but in a new stadium, a lot of people were convinced that it was a bit of a mirage. When you factor in his godawful defense and age, I think the offers were probably pretty low and the Twins decided to let him play out another year and see if that improved things. He promptly fell off a cliff and became useless. I have a hard time blaming the Twins too hard for that one - the deals we make in our head are not always there in reality. Willingham was the biggest contract in Twins history and he seemed perfect for Target Field so hoping for an increase in value wasn't crazy.
100% agreed on not having good players being the issue. The Twins haven't been able to deal for elite prospects because they haven't had them. Teams like the White Sox and Tigers have the elite players they can trade (but face the problem of not wanting to trade them because they are elite).
P.S. I forgot to include Span and Revere before though. Those were solid deals for the Twins, even if Meyer never worked out and May has been up and down. I wish we'd seen more of that but again, besides Perkins the Twins never had the guys to do the Span/Revere type deals.