If I was Jim Hendry...
Here are the moves I would make during the 2009 offseason:
I would sign IF/OF Eric Hinske to add some depth to the infield and outfield as well as provide a strong left-handed bat off the bench.
I would also re-sign John Grabow and bring him back as a set-up man for Carlos Marmol the closer for 2010.
Finally, Milton Bradley. I would offer Bradley and IF Mike Fontenot to the Los Angeles Angels in exchange for Gary Matthews Jr. This deal allows both teams to get rid of 2 guys with big contracts who don't want to be with their respective teams anymore. The Angels get Bradley who can DH or play RF and fill the void left by Vladmir Guerrero. They also pick up a good utility guy and left-handed bat in Mike Fontenot who can play second and third. Meanwhile, Matthews returns to the Cubs and Kosuke Fukudome moves back to right field and gives the Cubs a much better, more athletic defense in the outfield.
Next move I make is I offer Alfonso Soriano to the Mets in exchange for Luis Castillo. The deal gives the Mets a new left fielder who provides some power and is not unfamiliar with playing in New York. The Cubs get a second baseman who becomes their new leadoff hitter.
Now, this leaves a void in left field. What I would do is sign outfielder Josh Willingham.
With the starting pitchers I would offer P Carlos Zambrano, IF/OF Jake Fox, P Jeff Samardzija and IF/OF Micah Hoffpauir to the Toronto Blue Jays for P Roy Halladay & OF Vernon Wells.
The last move I would make is sign LHP Joe Beimel to add another lefty to the bullpen. With these moves made, here is what the 2010 Cubs roster would look like in 2010:
C Geovany Soto
C Koyie Hill
1B Derrek Lee
1B Eric Hinske
2B Luis Castillo
2B Jeff Baker
SS Ryan Theriot
SS Aaron Miles
3B Aramis Ramirez
LF Gary Matthews Jr.
LF Sam Fuld
CF Vernon Wells
RF Kosuke Fukudome
RF Josh Willingham
SP Roy Halladay
SP Ryan Dempster
SP Ted Lilly
SP Randy Wells
SP Tom Gorzelanny
RP Sean Marshall
RP Angel Guzman
RP Joe Beimel
RP Aaron Heilman
RP John Grabow
CL Carlos Marmol
