Kiss’Em Goodbye: Chicago White Sox

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.

Today we bid farewell to the Chicago White Sox, who signed Adam Dunn and watched the high-profile free agent lose complete confidence at the plate. His struggles mirrored the team's, as a horrific start put the White Sox in a hole from which they never fully emerged.

Signs of hope: So much went wrong for the Sox in 2011 that one has to be grateful simply for what went right. Although his slugging percentage dropped nearly 70 points from 2010, Paul Konerko still bopped 30 homers while hitting .302/.388/.520 in his age-35 season. Carlos Quentin wielded a potent bat (.254/.340/.499) before suffering a shoulder sprain in late August. Brent Lillibridge emerged as a strong utilityman, hitting .258/.340/.505 with 13 homers in 216 plate appearances and making highlight-reel plays while bouncing between five positions. Mark Buehrle had another Mark Buehrle season in the final year of his contract. Philip Humber evolved into a usable starter seven years after being the No. 3 pick in the amateur draft, helping to cover for Jake Peavy's injury. Converted infielder Sergio Santos took over closer duties after multiple incidents of arson by Matt Thornton. Chris Sale and Jesse Crain had even stronger seasons in support of Santos.

Signs of disaster: Start with the fact that three of the team's four highest-paid players had disastrous seasons. Dunn has been the majors' Least Valuable Player, hitting an impossibly awful .163/.293/.285 with 11 home runs en route to -2.3 WARP in the first year of a four-year, $56 million deal. Alex Rios has been sub-replacement level as well, hitting just .224/.262/.336 and sleepwalking in center field. He's still owed $38 million over the next three seasons. Peavy managed just 18 starts—his third straight season shy of 20—due to rotator cuff tendinitis and a groin strain. He's due $17 million next year plus a $4 million buyout for his 2013 club option. If there's something to be optimistic about, it's that strong peripheral stats en route to a 3.25 FIP are a better indication of his work than his 4.92 ERA.

Former first-round pick Gordon Beckham (.228/.293/.329) and rookie third baseman Brent Morel (.253/.295/.372), the team's only regulars under age 28, fell far short of expectations. John Danks and Gavin Floyd had surprisingly mediocre seasons with ERAs in the mid-4.00s, though they too fell short of their peripherals because the Sox ranked 11th in the AL in defensive efficiency, nine points below the league average.

Signs you can ignore: Organizational drama has been an ongoing sideshow, the South Side soap opera starring Ozzie Guillen, Kenny Williams, and Jerry Reinsdorf featuring clashes with coaches and the skipper's typically blunt criticism of his players. Guillen recently questioned his squad's efforts, but it's fair to wonder whether he's projecting his own ambivalence. The Marlins have eyed Guillen for their managerial vacancy, and the voluble skipper would rather depart Chicago if he doesn't get an extension beyond 2012. Given the troubling performances he coaxed out of this team, the Sox might be better off turning the page, though we'll all suffer for the loss of the fireworks. —Jay Jaffe, Baseball Prospectus

Bowden's Bold Move
There always is a certain afterglow—a honeymoon period—in the wake of a World Series championship in which players and managers bask. The city is in love with the team, which can do no wrong. Guillen leveraged that love into two contract extensions, unlimited popularity in Chicago and an apparent self-appointed license for unfiltered comments and bluntness.

However, the fact remains that the White Sox's 2005 championship was six years ago. The last time they won 90 games was five years ago. The White Sox will finish the 2011 season with a below-.500 record, and they've won just one playoff game since winning the World Series and have missed the playoffs each of the past three years.

With that said, the White Sox's bold move should be to part ways with Guillen. The Sox picked up Guillen's 2012 option back in January so he wouldn't go through this season as a lame-duck manager. Despite the fact Guillen is always fun and entertaining, the team has not lived up to its potential. A different leadership style might make sense. The White Sox plan to honor the $2 million option year, but Guillen has said he would like another extension. Seeing as how his team was below average in defense, baserunning and fundamentals, there isn't any reason to give him one.

Guillen has made it clear he doesn't want to come back as a lame duck on a one-year contract. Bold words from any manager, when one considers legendary skipper Walter Alston lived with 23 one-year contracts. Tommy Lasorda managed under 18 one-year deals, receiving only one multiyear contract in his managerial career before he headed to the Hall of Fame. Simply put, even a World Series championship shouldn't guarantee a manager job security if the team fails and underachieves in the seasons afterward. It's a performance-based industry, and Guillen and the White Sox did not perform in 2011. —Jim Bowden

Hopes and Fears
Best-case scenario ZiPS projection: 89-73
The season was disappointing, but the good news for the White Sox is that they really have nowhere to go but up. Dunn and Rios will be on much shorter leashes if they're looking up (way up) at replacement level again next year.

The Pale Hose's players had few good performances in 2011, so hovering around 80 wins in 2012 is on the low end of expectations. On the other hand, even with two gaping holes in the lineup and a rotation in which everyone pretty much disappointed, they're still near the .500 mark for 2011. They're not likely to get any huge breakouts among the starters, with the exception of lefty Sale, who was solid all year in the bullpen and can bring a lot more to the team pitching 180 innings. Beckham still has significant upside, though not quite as much as he did before his second clunker in a row.

Worst-case scenario: 70-92
To have an even worse season would take a lot, but there's always a chance that Rios and Dunn are finished as good starters, especially the latter. The White Sox will drop down to a 70-win team if they suffer significant starting pitcher injuries. In 2012, the White Sox will be less equipped to deal with injuries unless they bring in some free-agent help.

However, they will overpay this offseason, as the upcoming free-agent market does not feature many dependable starting pitchers. As seen this year, they don't have insurance for Beckham or Morel—expecting Lillibridge to remain an .845 OPS hitter is a bit premature. Konerko's having a second excellent year in a row, but he's going to be 36 by the start of the 2012 season. The Sox have no contingency plan to deal with his inevitable decline if it comes sooner rather than later. —Dan Szymborski, Baseball Think Factory

Organizational Future
One of the best stories in the minors this year was reliever Addison Reed, who went from Low-A to the big leagues in his full-season debut and could be the club's closer of the future.

With that out of the way, there's nothing else good to say about baseball's worst minor league system. Trades, drafts that are cheap and unimpressive, and an inability to conduct business internationally due to recent scandals have left the system without talent. Reed is the system's top prospect, but deciding who No. 2 is can be a long and depressing exercise. —Kevin Goldstein, Baseball Prospectus

A version of this story originally appeared on ESPN Insider .