Bill Smith's Greatest Weakness

Overall, Bill Smith's body of work as Twins general manager has been impressive. He took over at an extremely unenviable time, facing the task of letting two of the most popular and talented players in franchise history -- Torii Hunter and Johan Santana -- depart while keeping the team competitive. While that first winter was not a particularly strong one, Smith's Twins did surprisingly come within a game of the playoffs in 2008 and they won the division in each of the next two years.

The Twins front office under Smith has shown clear competency in a number of areas. These include targeting quality players in trades when their value is at a low point (JJ Hardy and Carl Pavano come to mind), acquiring valuable pieces through free agency (an area where Terry Ryan consistently struggled), drafting and being aggressive on the international market.

One area where Smith and Co. have not been particularly adept, however, is extending the contracts of their own players.

I'm not talking about the big fish. The heaping salaries of Justin Morneau and Joe Nathan are hard to stomach now, obviously, but no one could have predicted they'd suffer the type of major injuries they did. One can question the wisdom of paying Joe Mauer $23 million annually for the better part of the next decade, but it was a fair contract and the Twins would have been ravaged if they hadn't locked the MVP up after '09.

What I take issue with is some of the extensions Smith has given lesser players on the roster, and specifically the timing of those extensions. While he's shown an ability to bring in external players at bargain prices because their value is down, he tends to negotiate contracts with his own players when their value is superficially high.

Denard Span and Nick Blackburn, both of whom signed long-term deals buying out all their arbitration years prior to this season, are good examples. Each of these players performed in '08 and '09 at a level that far exceeded their minor-league track record. Blackburn's numbers seemed particularly difficult to sustain, as it doesn't take a hardcore sabermetrician to understand that when you constantly pitch to contact and don't draw ground balls at a particularly dazzling rate, you're liable to get blown up.

Both those players took major steps backwards this season, which shouldn't have come as an enormous surprise based on their histories and tendencies. Yet, the team is now locked into paying them both over the next 3-4 years at a rate based on their performance in the first two seasons. If Span and Blackburn continue to decline, they'll keep being paid as strong producers due to contract extensions that were totally unnecessary given that both were under team control for several more years.

Nick Punto represents another example of badly timed extension. If the team wanted to keep him around (which you'd have to guess they always did), they could have handed him a low-money extension after his historically dismal 2007 season. Instead, they waited until he put together a solid effort in '08 -- his last year under contract -- and had to pay him $8.5 million over two years to keep him from exiting via free agency. As a result they've had to pay him $4 million in each of the past two years to put up a sub-.630 OPS while characteristically battling injuries.

And then there's the Michael Cuddyer contract. This stands out to me as Smith's most egregious and baffling move yet. It's not so much the contract itself -- a three-year deal worth $24 million -- I have a problem with, although one could certainly question handing him such a sizable deal after a very pedestrian 2007 campaign. It's the stipulation regarding the club option. It had to be exercised five days after the end of the 2009 World Series, meaning the Twins had to decide whether or not they would pay Cuddyer $10.5 million in 2011 before seeing what he did in 2010.

I can't recall ever seeing a contract structured like this before. I can see why Cuddyer's agent would push for it, knowing that Cuddyer would be moving past the age of 30 in 2009 and understanding that the team might be more likely to activate the lucrative option after that season than after his 2010 season where age could start taking a greater toll on the right fielder's performance. What I don't understand is why in the world Smith would agree to it.

Was it really a deal-breaker? Was Cuddyer going to turn down an extension that paid him an average of $8 million annually after a relatively mediocre season because the club option was to be exercised after the final guaranteed year of the deal, as with any normal contract? By structuring the deal like this, Smith opened himself to the possibility that Cuddyer would have a great '09 campaign, making the option look like a no-brainer and prompting the team to activate it, then follow up with a poor 2010 season that cast doubt on his future productivity. Sure enough, that's exactly what happened and now the Twins are forced to pay Cuddyer's hefty salary next year when under normal circumstances they'd have the option of letting him walk or negotiating a new deal.

I like most of what Smith has done, but the burdensome long-term contracts of players like Span, Blackburn, Punto and Cuddyer stand as glaring examples of a pervasive weakness. This winter, he'll once again have the opportunity to extend the contracts of several players. I mentioned Francisco Liriano as a top priority on Wednesday, and players like JJ Hardy, Alexi Casilla and Kevin Slowey are also candidates for extensions.

I can only hope that the front office shows better judgment in handing out such extensions this winter, because unlike the Yankees, this team simply isn't equipped financially to deal with a multitude of poorly concieved contracts.