As the Cubs and Red Sox kick off an interleague series in Chicago on Friday afternoon, all eyes are upon Theo Epstein, who spent nine years as Boston's general manager and oversaw two World Series winners before departing last fall to embark upon a full-scale rebuilding effort as the Cubs' president of baseball operations. Epstein's new team owns the worst record in the major leagues at 21-42, while his old one is mired in fourth place in the AL East at 31-32. As if to underscore both teams' current situations, the series' first matchup pits Daisuke Matsuzaka, one of the expensive mistakes to which Epstein alluded earlier this week, in his second start back from Tommy John surgery, against Ryan Dempster, arguably both the best starting pitcher in this summer's trade market and the Cubs' most important trade chip. It's a tough matchup for the Sox given Dempster's strong performance thus far, but beyond today, the 35-year-old righty could be just what Boston needs.
On paper, the Red Sox biggest need remains the rotation. Despite the absence of their projected starting outfield of Carl Crawford, Jacoby Ellsbury and Cody Ross -- a trio limited to 44 games thus far, with Ross the only one likely to return in June -- and the underperformances of Adrian Gonzalez and Kevin Youkilis, the Sox rank second in the AL in scoring at 5.06 runs per game. On the flip side, their 4.65 runs per game allowed is the league's third-worst mark, and one for which both ends of the pitching staff bear responsibility given the Fair Run Averages (runs per nine, adjusted for defense, sequencing, and bullpen support) of the rotation (5.18) and bullpen (4.92). All five of Boston's starters have ERAs well above 4.00, and converted setup man Daniel Bard's struggles with his control led the team to demote him to Triple-A Pawtucket last week, creating the void that Matsuzaka is currently filling.
While the Sox would certainly love to salvage a greater return on the $103 million they invested in Matsuzaka, the reality is that they can't have much confidence in the 31-year-old Japanese import. Since 2009, Matsuzaka has pitched to a 5.08 ERA while making just 45 starts, his gaudy walk rate (4.5 per nine) catching up to him after solid showings in his first two seasons. He did show some promise in his June 9 return to the majors, striking out eight while walking one in five innings against the Nationals, but he also surrendered four runs and a homer, a reminder of the flyballing ways that have always made him an awkward fit in the AL East.
Dempster is a much more reliable starter, and not just because his 2.31 ERA currently ranks fifth in the NL. Since returning from a three-year stretch as closer in 2008, he has delivered four straight 200-inning seasons while averaging 33 starts per year and striking out 8.2 per nine. His 3.69 ERA as a starter for the Cubs in that span tracks almost perfectly with his 3.74 FIP; while his 3.3 walks per nine is a bit beefy, he's done a good job of limiting his home runs allowed to 0.9 per nine while pitching half his games in the Windy City, which is no small achievement. He's a groundball pitcher (though not an extreme one), which would certainly help him navigate Fenway Park, Yankee Stadium, Camden Yards and the other homer-friendly domiciles in which he'd often pitch if he were shipped to Boston.
Dempster is making $14 million in the final year of a four-year, $52 million deal; as a 10-and-5 veteran, he has the right to veto any trade, though it appears as if he's braced for the inevitability -- and perhaps imminence -- of one given the sight of a recent tête-à-tête with Epstein at Wrigley Field on Wednesday. Depending upon how much of his remaining salary the Red Sox are willing to take on -- no trivial matter given the team's $175 million payroll, and their other needs -- they may be able to find a fit with the Cubs, particularly given the fact that Epstein oversaw the drafting of virtually any prospect of interest in Boston's deep system. On the other hand, with no shortage of suitors (the Yankees and Dodgers are said to be the teams most interested in acquiring Dempster), Epstein can shop for a package with a more desirable blue chippers than Boston may be able to offer.
In terms of prospects, Dempster would certainly be more affordable to Boston than fellow righty Matt Garza, who as a former Rays hurler has more familiarity with the demands of the AL East. The 28-year-old Garza is on a much less expensive contract ($9.5 million), but he still has one more year of club control, and the Cubs have entertained the possibility of signing him to a longer-term deal — a move that makes less sense as part of a rebuilding effort than it does as a leverage-generating tool in trade talks. As for Epstein, the weekend is sure to carry a spate of questions about whether he made the right move in leaving Chicago for Boston. The Sox are a powerhouse, but one stricken with an incredible amount of misfortune in the injury department over the last few years, creating problems that their lack of roster flexibility has made more difficult to solve; this is a team with $282 million committed to Crawford, Adrian Gonzalez, Josh Beckett and John Lackey beyond this year. Epstein's current roster has even deader financial weight in the form of Alfonso Soriano ($36 million remaining after this year), not to mention $22 million they're already eating in the form of commitments to the since-departed Carlos Zambrano and Marlon Byrd. But in overhauling the Cubs, he has the chance to avoid some of the mistakes he made in Boston — skipping the posting fees, perhaps, and the pressure to make a move simply to keep up with the Yankees. He can take one more step towards a brighter future for the Cubs by dealing Dempster to his old club.