Kiss 'Em Goodbye is a series focusing on MLB teams as their postseason dreams fade—whether in September (or before), the League Division Series, League Championship Series or World Series. It combines a broad overview from Baseball Prospectus, a front-office take from former MLB GM Jim Bowden, a best- and worst-case scenario ZiPS projection for 2012 from Dan Szymborski and Kevin Goldstein's farm system overview.
Baseball Prospectus' Take
Signs of hope: Starlin Castro has progressed at the plate and held his own on the field (when he's remembered to face the right way), pacing Cubs position players with 2.8 wins above replacement at age 21. Setup man Jeff Samardzija has looked more like a reliever than a receiver for the first time since 2008. The Cubs have gotten 212 1/3 innings and a 6.23 ERA out of a fifth-starter slot that has rotated between Rodrigo Lopez, Casey Coleman, Doug Davis, James Russell and Ramon Ortiz. A healthy Andrew Cashner could fill that role in 2012 if he makes it out of the Arizona Fall League intact. With former GM Jim Hendry out of the picture, the Cubs will conduct an exhaustive search for his successor, who likely will come with a remarkable résumé and a blueprint for sustained success. Despite the team's struggles, fans have continued to flock to Wrigley Field, enabling the Cubs to place fourth in NL attendance for the third straight season.
Signs of disaster: The Cubs are among baseball's least efficient spenders, converting the National League's third-highest payroll into its third-worst winning percentage. Among the major culprits is an inability to catch the ball. Led by the Senior Circuit's worst-fielding third baseman (Aramis Ramirez, minus-12.6 fielding runs above average) and pitcher (Carlos Zambrano, minus-3.6 FRAA), the North Siders have turned just 69.6 percent of balls in play into outs, the lowest success rate in baseball. Thanks in part to their faulty fielding, the Cubs can claim only a single starter (Matt Garza) with an ERA below league average, and closer Carlos Marmol leads the league in blown saves while dealing with dramatically reduced velocity. Unfortunately, the Cubs' miscues can't be chalked up to inexperience; with an average age of 29.6, they've fielded the majors' fifth-oldest club, and one of the youthful bright spots on the 2010 team, Tyler Colvin, hit .147 in his sophomore season. Although Hendry has been relieved of his duties, the largesse that led to large contracts during his tenure continues to cripple the Cubs, who have $38 million committed to Zambrano and Alfonso Soriano—fresh off a replacement-level performance—for 2012.
Signs you can ignore: Second baseman Darwin Barney became a fan favorite for his scrappy style and hot start to the season (.326/.351/.449 batting average/on-base percentage/slugging percentage in April), but he's hit .263/.303/.326 thereafter, showing himself to be utility material. The Cubs will continue to court second-division status unless they disregard that initial success and reduce his role (or at least hit him lower in the lineup). Overall, Cubs batters have struggled in the clutch, hitting .232/.314/.373 with runners in scoring position compared to a .259/.315/.404 overall line, a pattern that has made the offense appear slightly worse than it is and isn't likely to be repeated. —Ben Lindbergh, Baseball Prospectus
Bowden's Bold Move
It's more like bold moves. The Cubs should start their offseason by hiring Hall of Famer Pat Gillick as senior VP of baseball operations and Red Sox assistant general manager Ben Cherington as GM. Then, they should let Carlos Pena leave via free agency, release Zambrano, decline the $16 million option on Ramirez, trade Marlon Byrd and talk Ryan Dempster into accepting a trade to a contending team. Chicago should reinvest all of its potential savings into player development and scouting, and that includes staffing in addition to players. The Cubs should pursue the game's top evaluators from other teams and be willing to pay them at the top dollar. Then Chicago should go to MIT, Harvard, Stanford and every other top college in the country and hire some of the best computer science and statistical minds available and start building an analytical and research department to start catching up with the times and break new ground.
There shouldn't be an amateur player available internationally that the Cubs don't scout and at least attempt to outbid—even the Yankees—for their services. Every top-round talent who falls on the board because of signability in next June's draft should be selected and signed. The Cubs should sign some Type B free agents to one-year contracts with hopes that these stopgap-type players get traded at the deadline or bring them a sandwich pick in the following year's draft. The hirings of Gillick and Cherington would put them on that path for both short- and long-term success. —Jim Bowden
Hopes and Fears
Best-case-scenario ZiPS projection: 85-77
The Cubs have had one of the worst performing rotations in baseball this year, with Dempster, Zambrano and Randy Wells all having poor seasons. There's a reasonable expectation for a rebound to at least adequacy for all three, assuming that Zambrano does in fact return—no guarantee after the sparks last month that led to his season ending prematurely. The team doesn't have a lot of offensive upside with several players well into their decline phase and some pretty big unknowns. Castro is the exception but not enough to put the Cubs in the hunt without some serious luck. I assumed a 50 percent chance of the Cubs picking up Ramirez's option.
Worst-case scenario: 69-93
Although this team knows how to underperform, there are too many talented players for the Cubs to threaten 100 losses. Even this year, with very little going right, they will fall short of the century mark. It's unlikely that the rotation gets even worse next season, and Marmol is also a good bet to have a much better season, which makes it very difficult for the team to be Astros-level bad. This could change depending on what direction a new GM takes, but after 2011, the team would have to eat most of Zambrano's or Dempster's contract, so it may hang on to them for a final season if the organization chooses a rebuilding route. —Dan Szymborski, Baseball Think Factory
The Cubs have a strange minor league system. It's more deep than star-studded, with plenty of potential big leaguers but few who can actually help turn around a moribund franchise. The most likely player to help in 2012 is center fielder Brett Jackson, the club's 2009 first-round pick who hit .274 with 20 home runs in 23 stolen bases in 115 games split between Double- and Triple-A. He'll fight for a job next spring and likely have one by midseason, and although he's an outstanding athlete with above-average power and speed, his alarming strikeout rate (138 in 431 at-bats this year) prevents scouts from seeing him as a true impact player in the big leagues. —Kevin Goldstein, Baseball Prospectus
A version of this story originally appeared on ESPN Insider .