I haven't said much about the Paul Maholm extension, partly because I had mixed feelings about it at first. Yes, long-term contracts for good players who aren't yet eligible for free agency are generally a good idea, because the player will generally exchange some future value for long-term financial security. But Maholm has only had one really good season, and while I think a lot of the improvement he showed last year was legitimate (he maintained his low 2007 walk rate while bumping up his strikeout rate), he had much better luck with the Pirates' shoddy defense than most of the rest of the staff did. Batters hit .273 against Maholm on balls in play, whereas they hit, for example, .311 against Zach Duke and .338 against Ian Snell on balls in play. That's not entirely the business of the defense, but a lot of it is. Maholm is thus likely to be at least superficially worse in 2009, and so it's possible that the Pirates are signing Maholm at the peak of his value.
In the end, though, that doesn't in itself make the signing a bad idea, because if Maholm does have another good season in 2009, buying him out of his first year of free agency (2012) would be that much harder.
In the end, I think I like this deal because the Pirates get an option for 2012. It's not cheap (effectively, it's $9 million--$9.75 million with a $750,000 buyout), but it does reflect real planning. As I've written many times, the team that Neal Huntington and Frank Coonelly inherited was built as if it wouldn't still exist in 2010. Most of its key players (Jason Bay, Freddy Sanchez, Adam LaRoche, John Grabow, Damaso Marte, Xavier Nady, Salomon Torres) would be eligible for free agency after the 2009 season (and Jack Wilson had a 2010 option that would probably be bought out), and there was very little in the farm system to potentially replace them.
The best things Huntington and Coonelly have done involved revamping the Pirates' Latin American operation and their drafting strategies, but they've also done well to identify and address the 2010 Problem. The lack of starting pitching depth in the minor league system was downright scary, so they dealt Nady and Marte for a package that included three young pitchers who are capable of starting. They also signed Sanchez to a deal that could keep him in Pittsburgh in 2010. These moves probably won't have a huge effect on the Pirates' next contending team, but they are likely to help prevent the 115-loss stinkbomb that Dave Littlefield had ready to explode after all his players left.
The Pirates' new management also seems to have figured that, with the 2010 Problem fast approaching, their next window for contention probably opens in about 2012. So they've signed three players in their arbitration years--Ryan Doumit, Ian Snell and Maholm--to long-term deals that provide the team with 2012 options they wouldn't have otherwise had.
The team will therefore have a bunch of flexibility in 2012 to react to a variety of possibilities. If the Bucs are able to build a good core of minor-league talent and if Doumit, Snell and Maholm are effective then, they can keep them and make a run at contention. If any members of that trio are ineffective, they can drop them after 2011 and spend the money on players who will help more. And if the minor leagues aren't churning out talent by then, the Pirates can exercise the trio of options and then look to make trades, or decline the options, offer arbitration and collect draft picks.
The extensions for Doumit, Snell and Maholm thus suggest that the Bucs are looking at a point far into the future. To me, these contracts really aren't about 2009 to 2011, when the Pirates would have had those players under control anyway. They're about the possibility of contending in 2012.