Chicago Cubs: Paying players to play for other teams

One possibility is a swap of bad contracts. The Cubs had a semi-successful bad contract swap in 2009 when they traded outfielder Milton Bradley for starting pitcher Carlos Silva.

Switch-hitting Bradley was supposed to bring balance to a mostly right-handed hitting lineup. But after fitting in with a unique clubhouse in Texas, Bradley never did fit in with the Cubs. In 2010 Silva nearly pitched himself into the All-Star game in the first half of the season. But he did not pitch anywhere near as well in the second half of the season.

Aside from a trade of Chatwood for Russell Martin it’s difficult to see a place where there would be a bad contract out there that might fit the Cubs needs. Martin could have filled the role of the veteran backup catcher for the Cubs.  Chatwood could have been a buy-low starting pitcher with a lot of potential upside for the Toronto Blue Jays. However, Martin has since been traded to the Los Angeles Dodgers.