How'd that work out?

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Will Money Finally Buy the Cubs a World Series?

Kavitha A. Davidson is a former Bloomberg View columnist.
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The big news out of Major League Baseball's winter meetings is that Chicago might just be the new center of the baseball universe. Of course, Windy City fans, especially those on the North Side, have seen hot-stove league dreams turn into summer nightmares before. 

This morning, news broke that the Chicago Cubs had signed Jon Lester, the marquee pitcher of this free agency period. The six-year, $155 million deal is the cap to an already busy off-season in which the woeful Cubs have proved they’re willing to spend to win now. On Monday, the Cubs signed right-hander Jason Hammel to a two-year, $18 million contract, bringing him back after trading him to the Oakland A’s in July. The next day, they traded for catcher Miguel Montero, sending two minor-league pitchers to the Arizona Diamondbacks in exchange for the two-time National League All-Star.

It adds up to the culmination of three years of rebuilding by Theo Epstein, who took over as general manager after the 2011 season. Epstein, who oversaw the Boston Red Sox’s first championship in 86 years in 2004, outbid his former team by $20 million to bring in Lester to Chicago.

Frustrated Cubs fans are now seeing Epstein’s plan come to fruition, thanks in no small part to owner Tom Ricketts’s wallet. Epstein managed to shed $41 million from last season’s payroll, and Ricketts is confident in the strength of an impending television deal to finance his team’s off-season shopping spree. As of October, the Cubs were valued at more than $2 billion.

In November, Epstein hired manager Joe Maddon away from the Tampa Bay Rays to mold his team of young, budding stars. In Tampa, Maddon took a team with talented youths but little financial support and turned it into a perennial player in its division. The Cubs now have the best farm system in baseball and are chock-full of talented position prospects. And while Chicago might have small-market talent, it also has big-market money, allowing the team to supplement the young lineup with expensive veterans on the mound.

The Cubs’ splashy signing of Lester shouldn’t detract from what’s happening on the South Side, however. The Chicago White Sox have had a busy offseason of their own, and are certainly contenders to once again compete in the American League Central. This week, the team traded for former Cubs and A’s starter Jeff Samardzija, while signing New York Yankees closer David Robertson to a four-year, $46 million deal.

The White Sox began shoring up their inexperienced bullpen by signing lefty reliever Zach Duke to a three-year, $15 million contract in November. They also signed veteran first baseman and designated hitter Adam LaRoche to a two-year, $25 million deal.

While the Cubs’ game plan seems cohesive and streamlined, the White Sox appear to be taking more of a post-it note approach. But with ace Chris Sale and reigning Rookie of the Year Jose Abreu, it’s not hard to imagine their off-season moves paying off in a division no longer dominated by the Detroit Tigers.

Those hoping for a Windy City Series have to realize the odds are very long. The Cubs and White Sox haven't met in the postseason since 1906. And the Cubs tried something similar after the 2006 season -- notably, hiring manager Lou Pinella and signing Alfonso Soriano  -- that resulted in getting swept out of the playoffs twice and inflicting the team with long-term salary deadweight.  

But for now, at least, let's celebrate that baseball isn’t just relevant again in Chicago -- it’s exciting, headline-grabbing, the talk of the town. 

This column does not necessarily reflect the opinion of Bloomberg View's editorial board or Bloomberg LP, its owners and investors.

To contact the author on this story:
Kavitha A. Davidson at

To contact the editor on this story:
Tobin Harshaw at