Chicago Cubs Long-Term Focus: What has CC Sabathia to do with Ryan Dempster?

Posted on April 12, 2011

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Could New York Yankees ace left-handed pitcher CC Sabathia trade in his navy pinstripes for royal blue ones this winter? It’s not as far-fetched as it sounds. Believe it or not, the answer could ride on the 2011 performance of Chicago Cubs starter Ryan Dempster.

By now, well-informed baseball fans well know that Sabathia has an opt-out clause in his current Yankee contract, to take effect at the end of this season. This winter and this winter only, Sabathia will have a chance to void a pact that guarantees him $92 million over the seasons 2012-2015. That such a clause exists is testament to the foresight of Sabathia and agents Greg Genske and Scott Parker. In December 2008, when Sabathia signed his megadeal amid a second consecutive bear market for free agents, the figures in the contract itself looked obscene. The Yankees likely never imagined Sabathia would be tempted to seek greener pastures.

Things are different now. Cliff Lee, a lefty of similar stature but with less durability and two years on Sabathia, got $120 million over five years from Philadelphia in December. The offseason saw Jayson Werth get $126 million and Carl Crawford get $142 million on seven-year contracts. For the first time in baseball history, serious murmurs about a $300-million deal began to surface around Albert Pujols of the Cardinals. The market today is all bull, and if Sabathia does not opt out after 2011, he could be leaving $30 million or more on the bargaining table.

Assuming Sabathia does opt out, the Yankees remain the favorites for his services. Losing out on Lee last winter ensured GM Brian Cashman will reach as deep into the corporate wallet as his arm will go to find money for the only true ace the Yankees have or can feasibly acquire within the year. The Los Angeles Angels (translated all the way out of Spanish, that’s just “The The Angels Angels”) might get involved, especially because the team is apparently far from a deal with incumbent ace Jered Weaver on a contract beyond 2012, but GM Tony Reagins may not have the flexibility for such an expenditure after the gaudily expensive Vernon Wells acquisition in January.

Here enter the Cubs, dark though their horse in this race might be. In an offseason when the team could shed as much as $66.5 million from its current payroll, no free agent is necessarily beyond their means. In the case of Sabathia, though, the practicality of the Cubs’ prospective interest is wholly contingent upon Dempster.

Most Cubs fans believe Dempster signed a hard four-year contract after the 2008 season, locking him in at an average annual salary of $13 million through 2012. Not so: Dempster has a $14-million player option for 2012, which would actually represent a modest pay cut for the former All-Star. He has the right to test the free-agent waters at the end of this season, which threatens to be a second straight losing campaign and the start of an earnest rebuilding effort.

Dempster, by all accounts, loves Chicago. He was an ardent fan of the Blackhawks en route to the team’s Stanley Cup victory in 2010; he rides his bike to work; the clubhouse is his for the taking. Still, he has eclipsed 200 innings in three straight seasons, struck out 208 and won 15 games for the 75-win Cubs last season, and has an ERA just a tick over 3.50 since the beginning of the 2008 campaign. If he has another solid year, he stands to earn something slightly better than the three-year, $33-million deal former teammate Ted Lilly signed last October to stay with the Los Angeles Dodgers.

Maybe one last hurrah with the Cubs will be preferable for Dempster. Maybe he will want to stick around and try to lead the team back to prominence, thereby setting himself up for an even bigger payday. Then again, maybe he will pitch poorly (his 6.30 ERA and four homers allowed through three starts are hardly sufficient cause for alarm, but they aren’t encouraging, either) and take refuge in the option.

It is possible, though–perhaps even probable–that Dempster will pitch will enough and decide to test free agency for more long-term security at age 35. He may well find it with Chicago, after all, since the team will have a bit of money to spend, but then he may find it elsewhere. And while he drifts, the Cubs will have his $14 million for 2012 to play with. If GM Jim Hendry is smart, he will take a moment to consider: Isn’t CC Sabathia worth $9 million more per season than Dempster?

Even I, a firm Dempster apologist, think Sabathia is the better investment. The Cubs may be able to turn things around in 2012 and compete seriously on the strength of breakout performances by key youngsters like Brett Jackson and Trey McNutt, but it sure seems unlikely. If Dempster gives him the opening, Hendry needs to make a more future-first choice. Dempster is over three years Sabathia’s senior, and Sabathia is a true ace. The difference between them in a given season is roughly two wins above replacement. That gap is only going to grow from 2012-2015, as Dempster declines through his late 30s.

This is all hypothetical. As likely as not, one of the two men gets hurt and stays put with the security of their present deal. Another scenario could see Sabathia turn his nose up at the Midwest altogether, eschewing Chicago for a return home to the West Coast.

Even so, the reasons for Cubs fans to monitor this situation closely should be obvious. Sabathia did what he said he wanted to do when he signed with New York, winning the World series in his first season with the Yankees in 2009. It may be that the East Coast no longer suits him, and if so, the Cubs are the next team in line in terms of fiscal wiggle room if Dempster goes.

You know what’d be fun? What if the Cubs made the heaviest investment ever in free agents, signing Sabathia and Prince Fielder? Talk about weighty expectations on that team, eh?

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