If there has been a running Cubs offseason theme, his name is Jake Peavy. That's to be expected, I suppose -- the Cubs don't have much flexibility in the free agent market, and aren't in the running for uber-expensive guys like C.C Sabathia and Manny Ramirez. This is a blessing in disguise; one shudders at the thought of giving the aging Ramirez a backloaded contract that keeps him on the payroll until age 42, or at paying hundreds of millions for Sabathia, who has thrown almost 500 innings in the last two seasons combined. Buying up either player would be paying more for past accoloades than future performance, and that's the last thing the Cubs need.
So if the Cubs are going to acquire a big name in the offseason, it's going to be through a trade, and if it's going to be a trade, it's going to be Jake Peavy. The only problems are these: the Padres don't like the Cubs' offer, and the Braves have a better one, at least according to Ken Rosenthal:
The risk in that strategy is that it might cost them the players the Braves are willing to trade for Peavy — shortstop Yunel Escobar, either right-hander Charlie Morton or left-hander Jo Jo Reyes and either center fielder Gorkys Hernandez or Jordan Schaefer.
The Cubs might be offering a more established pitcher, left-hander Sean Marshall and perhaps a top prospect of their own, Class A third baseman Josh Vitters. But Escobar likely is the best player in either team's proposal, and the Cubs cannot give the Padres a center fielder as promising as Hernandez or Schaefer.
Rosenthal admits that the Padres must at least be interested in the Cubs' offer, or they would have shipped Peavy to the Braves already, but still: this isn't looking good. Compounding the problem is the Cubs handling of Ryan Dempster's contract situation. The Cubs offered Dempster the standard hometown discount offer, around $50 million for four years, according to Paul Sullivan. The problem with this is not that the Cubs made the offer, though it could be argued that Dempster had an outlier of a year last year (his next best season to last year's was in 2004, when he posted a WHIP of 1.403) and is set to regress to the mean. The problem is that the Cubs are effectively juggling one ace for the other -- trying to re-sign Dempster on the one hand, trying to trade for Jake Peavy on the other.
It seems unlikely the Cubs will make the Peavy trade work. It seems unlikely Dempster will want to re-sign with the Cubs for below market value (though, if this is to be believed, maybe he will). So either the Cubs will end up with one pitcher, or the other, or -- nightmare scenario time -- neither. Here's hoping Jim Hendry knows how to juggle.