St. Louis Cardinals (John Mozeliak)
Mozeliak inherited the GM role from the very popular Walt Jocketty and, as such, was faced with some early criticism from those who expected he would never be able to fill Jocketty's shoes. The Cardinals success in 2009 should quiet his critics, if only for a time. Mozeliak greatly improved his squad over the course of the season, acquiring Matt Holliday, Mark DeRosa, John Smoltz, and Julio Lugo, seemingly perfectly positioning the Cards for a run deep into the postseason. Although it didn't work out that way, Cards fans have to be very proud of the team their organization fielded for them.
Unfortunately, Mozeliak won't have any time to rest on his laurels. He already accomplished his first order of business, wrapping up Tony LaRussa for another year, putting to rest rumors that the legendary manager was feuding with the organization and considering a move. Now, there is the question of personnel, starting with those guys he signed in July and August. Holliday, DeRosa, and Smoltz are all headed to free agency, as are Troy Glaus, Rick Ankiel, and Joel Pineiro, leaving St. Louis with more unanswered questions than either of their primary rivals, the Cubs and the Brewers. At the very least, between now and April they will need to designate a left-fielder, a third-baseman, and two starting pitchers. They have promised to actively pursue resigning Holliday. If they could accomplish that, they could probably get away with an in-house solution at third, as David Freese tore up Triple-A and looked good in his September audition. But if Holliday, who will likely have two suitors in New York and one in Boston, proves too expensive, Mozeliak's winter could be very challenging.
As usual, the Cardinals will look for inexpensive reclamation projects to send to Dave Duncan's school for thirty-something castaways. Smoltz may be interested in attending a second semester and Braden Looper looks like he could use a refresher course after a significantly down performance in Milwaukee. Other good matches include Doug Davis, Jon Garland, Justin Duchscherer, and Carl Pavano.
Chicago Cubs (Jim Hendry)
High expectations going into the season overshadowed the fact that the Cubs accomplished something they had not done since 1972, securing at least three consecutive winning seasons. Last winter, Hendry made two major acquisitions, Kevin Gregg and Milton Bradley. Both were unmitigated disasters in 2009, while the very popular Mark DeRosa, sent to Cleveland for prospects, ended the season on the Division Champion Cardinals.
There weren't many bright spots for the Cubs this season. Derrek Lee had his best season since 2005. Randy Wells contended for Rookie of the Year. Ted Lilly, Carlos Zambrano, and Ryan Dempster all pitched fairly well, but all missed time with injuries, and none won more than twelve games.
The good news is, the Cubs have a lot of talent signed for next year. It's expensive talent and, this season at least, it was underperforming talent. But the odds would suggest that they will be better in 2010, even if they just stand pat. The only significant free agent they stand to lose is Rich Harden. Assuming the new ownership has pockets as deep as what Hendry has grown accustomed to, he will have some serious flexibility for pursuing his needs. He will have to decide whether to prioritize center field, second base, the back-end of the rotation, or middle-inning relief. In each and every case, the Cubs have modest in-house options (Kosuke Fukudome, Mike Fontenot, Tom Gorzelanny, Jeff Samardzija, etc.), so Hendry shouldn't be pressured if ideal candidates don't present themselves. He needs to resist the temptation to add more big, bad contracts to the collection the Cubs have already stockpiled.
As a Cubs fan, I can say I would really like to see them reel in a true center-fielder, but there aren't many on the market. Mike Cameron might make a good fit, if they could sign him to a one-year deal (with an option). A relatively cheap, defense-oriented guy like Coco Crisp might also be tempting.
Late in the season everybody assumed that the Cubs would dump the unpopular Bradley prior to next season, but the signing of hitting coach Rudy Jaramillo may indicate that they are considering giving the highly-talented switch-hitter a second chance. Certainly, his value on the trade market has never been lower.
Milwaukee Brewers (Doug Melvin)
The Brewers have been, over the last five years, one of the best run franchises in the league, and they enter 2010 with many solid pieces in place. However, Melvin's window for chasing a championship with the current core of players won't be open for a whole lot longer. The Brewers best player, Prince Fielder, will be a free agent after 2011, as will Rickie Weeks, J. J. Hardy, and Dave Bush, followed by Corey Hart in 2012.
From my perspective, it looks like the time is now. The only hole in the Brewers lineup going into 2010 is center-field, where Mike Cameron is becoming a free agent. Cameron loves Milwaukee and is a popular clubhouse presence, so re-upping is hardly out of the question. They may also consider promoting somebody like Lorenzo Cain or Chris Duffy.
The point is, Melvin needs to focus his attention this offseason on pitching. Things are not as bad as they seem. Although the Brewers were last in the National League in rotational ERA this season, they will enter 2010 with a healthy David Bush and (hopefully) Chris Capuano. Yovani Gallardo, Manny Parra, and Carlo Villanueva will all have an additional year under their belts. Several prospects, most notably Jeremy Jeffress, are rising rapidly through the ranks. And, for what it's worth, they still have Jeff Suppan.
What the Brewers really need (as C. C. Sabathia proved in 2008) is a veteran workhorse to insert into the front of their rotation, taking the pressure off Gallardo, especially, and everybody on down. Easier said than done, right? There aren't a whole lot of those pitcher in the game and John Lackey is the only one on the free agent market this season. As a Boras client, he's probably out of their price range.
However, what Milwaukee does have is a plethora of young talent, both major-league ready and in the lower rungs of the system. As it stands, Weeks, Hardy, Casey McGehee, Alcides Escobar, and Mat Gamel will be fighting for three starting positions on the infield. Angel Salome and Jonathan Lucroy may be ready to share major-league catching duties as soon as next spring. Scouts around baseball are fawning over the raw skills of Jeffress, Brett Lawrie, and Cutter Dykstra. Melvin could part with two or three top prospects (and other couple middle-tier guys) without totally gutting the system, and that might be all it takes to land Roy Halladay.