Chicago Cubs: Moves made before 2009 helped set the table for the downfall of the Hendry era
The Cubs in the late-2000s were in full “win now” mode under former GM Jim Hendry. While still having the core of Lee, Aramis Ramirez, Alfonso Soriano, Geovany Soto, Carlos Zambrano and Ryan Dempster going into 2009, Hendry decided to make some bold changes.
Most significant moves were trading away Mark DeRosa and Kerry Wood to the Indians while signing controversial outfielder Milton Bradley and traded with the Marlins to get Kevin Gregg. DeRosa was a big part of the lineup, and Wood had transformed himself into an All-Star closer. Bradley’s one year with the Cubs in 2009 was a disaster, and Gregg struggled mightily as the closer. Was the failure of the 2009 team all on these moves? No, but they were a big factor.
As mentioned earlier, 2009 was the last year they were competitive for a while. The final years Hendry served as GM in 2010 and 2011 resulted in losing records while having an enormous payroll and little on the farm. 2009 showed that the team that won back-to-back division titles in 2007 and 2008 was starting to decline. “Major” changes he made in his final few years mainly included trading away some veterans for very little and patch-working some of the holes on the MLB roster.
I think it is fair to say Hendry really cared and tried hard to win. He was pressured by the Chicago Tribune to spend a lot to increase franchise value. In the final few years, he was stuck with an old expensive car that could not run well, and he had little he could use to fix it. 2009 was that turning point from competing to being stuck with a mess.