9. Todd Hundley - 4 Years, $23.5 Million (2001)
The biggest thing Todd Hundley had going for him when he signed with the Cubs in Dec. 2000 is the fact he was the son of the most popular and well-known catcher in franchise history, Randy Hundley.
That added a lot of excitement to his signing, which disappointed almost immediately. There was drama over who was getting reps behind the plate between Hundley and Joe Girardi early in the year and the former did himself no favors at the plate, batting .167 on the year. That marked a stark contrast from what he'd done in years prior, given from 1996-2000, he averaged 24 home runs and an .860 OPS.
He improved, marginally, in 2002, but still fell well short of expectations and didn't even finish out his contract with the Cubs. Incoming GM Jim Hendry shipped Hundley to the Dodgers in Dec. 2002, adding two key pieces of that 2003 team in Eric Karros and Mark Grudzielanek.
The deal, in and of itself, did nothing to solidify the catching situation in Chicago - but at least the front office managed to turn it into something to help the team win before it was all said and done.