Chicago Cubs: Five worst free agent signings in history

Aaron Miles – signed 2008 – 2 years, $4.9 million

I know, I’m finishing off this slide with Aaron Miles, not Alfonso Soriano, Todd Hundley – or even Candy Maldonado.  This one was a frustrating signing for me.  I didn’t like the signing when it was made and I knew the Cubs would never see one good penny from this deal. I know, I’m bitter.

Miles was brought in to be a switch-hitting second baseman and someone who could add some flexibility to the Cubs lineup.  Coming off a very good year with St. Louis where he posted a line of .317 average, 4 home runs, and 31 RBI in 134 games. Looking past that lone season, he was a career .289 hitter with a World Series ring in tow.

The signing came off as questionable to a lot of Cubs fans, Miles was really a utility player who could be moved around.  The team already had someone who fit that role in Mark DeRosa.  DeRosa was one of the more popular Cubs players, not just with the fans but in the locker room as well. DeRosa was a “jack-of-all-trades” kind of guy who played anywhere and everywhere.

Not too long after the signing of Miles, DeRosa was traded away to Cleveland.  As DeRosa’s replacement, Miles didn’t fill his shoes at all.  In his one season with the Cubs, Miles had a .185 batting average with no home runs, five runs batted in and a mere three steals.

Because the signing of Miles caused the Cubs to move DeRosa (probably would have happened anyway with the Cubs cutting payroll) I think Miles earned this spot … it was the only thing he earned as a Cub.