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 of this season from Buster Olney, a take from Baseball Prospectus, a look toward an immediate 2011 move courtesy of Rumor Central and Kevin Goldstein's farm system overview. You can find all the teams on one page by going here.

Now, it's time to kiss the Chicago White Sox goodbye.

The overview

The starting rotation the White Sox hoped would be dominant turned out to be much less than that. Jake Peavy struggled and then got hurt, Mark Buehrle slogged through parts of the season and Chicago finished in the bottom half of the majors in ERA. Coming off a 2009 season in which Carlos Quentin was constantly banged up, the White Sox opted to not fill the DH spot with someone like Jim Thome—and it was a decision that came back to hurt them, because Thome had an outstanding season for the Twins, and the White Sox spent $3.8 million on Manny Ramirez to fill the DH spot in September (with virtually no return on the investment). Gordon Beckham was a victim of the sophomore jinx, and Bobby Jenks was a disaster whenever he was asked to pitch in day games.

Also, from the start of spring training right up until the final week of the season, the tempestuous relationship between GM Ken Williams and manager Ozzie Guillen played out like an ugly reality show, involving many tweets and tweaks.

Paul Konerko merited top-five consideration for Most Valuable Player—in the final year of his contract—and Alex Rios lowered his hands in his swing and was greatly improved. Matt Thornton was regarded by advance scouts as one of the most dominant left-handed relievers in the game, and if the White Sox ever decide to move him—which is unlikely at this point—there would be a flush market.

Guillen has indicated that he will return to the White Sox in 2011, but for sanity's sake, he and Williams need to work out their personal differences. Chicago wants to retain Konerko, but if he departs there will be a huge hole in the lineup that needs to be filled with someone like Adam Dunn. The White Sox have to hope that with an offseason of reflection and rest, Beckham gets back to being as good as everyone thinks he'll be. And it's probably time for the White Sox to decide whether they think Jenks is suitable to be their closer, or if they should spend to get someone like Rafael Soriano or make a trade for the likes of Heath Bell. —Buster Olney, ESPN Insider

Baseball Prospectus' take
What went right: Konerko, but we'll get into that in a moment. More fundamentally, the "go for it" instinct remains alive and well in Bridgeport: Williams adapted in-season to losing Peavy by trading for Edwin Jackson in July—at cost, since Daniel Hudson is an excellent prospect—and tried to add punch by claiming Ramirez off waivers in August. Rios bounced back from making a bad first impression, produced toward the upper range of his best possible PECOTA projections and proved to be a fine center fielder, giving the White Sox strength where they'd been weak.

What went wrong: The Twins changing the competitive level of the American League Central, for starters, because the White Sox are currently an 85-to-90-win team in a division in which that's no longer good enough. The failure to get a potent lefty-batting DH to replace Thome hurt, and adding Ramirez was too little too late (made worse by Manny's power not making the trip to Chicago). Beckham massively disappointed lofty expectations generated by his rookie season, but hit well enough in the second half to recapture some promise. The rotation was supposed to be the club's platform for success, but struggled to a seventh-place tie in the AL in Support-Neutral Value Above Replacement (SNLVAR).

The key number: .321. When Williams took Juan Pierre off the Dodgers' hands in the offseason, the speedster was talked up as the solution to the White Sox's longstanding problem at the leadoff spot. Pierre handily led the league in stolen bases, thrilling fantasy owners, but he was also primarily responsible for the team's leadoff OBP of .321, which ranked 17th in the majors. Sox leadoff men also managed to slug just .300, next-to-last in the majors. Considering that's what the Sox were also getting out of their left fielder, a position usually associated with bigger offensive numbers, trying to add a speedy piranha of their own to Ozzieball only ended up biting the Sox.

What won't happen again: Konerko had a career year at 34, so enjoy this like a fine wine and then realize that nothing this good stays this good forever. (Not naturally, at any rate.) Paulie has been a White Sox stalwart for 12 years, and while he's hit more homers in some other seasons— and hit for a higher average—this year he set career highs in OBP, slugging, True Average (.326), Runs Above Replacement, Wins Above Replacement and more, ranking behind only the Tigers' Miguel Cabrera in the AL among first basemen in most value metrics. Konerko is headed into free agency, but whether the market pays him for 2010 or for a long career with a less stratospheric level of quality work will be interesting to see. —Christina Kahrl, Baseball Prospectus

Rumor Central: 2011 options

Who's on first? Konerko has been a regular on the South Side for more than a decade, but the big numbers he put up on the field in 2010 could translate to big dollars off it. The White Sox would love to have him back but might balk at a three-year deal for a first baseman who will be 35 by Opening Day. Konerko likes playing for Guillen—who will return in 2011—but so far has given no indication whether he will give the Sox a hometown discount. Dayan Viciedo will be handed the keys to first base at some point, but the 21-year-old could use more seasoning. The White Sox took plenty of heat this season for counting pennies and not bringing back Thome, so that could play into Konerko's favor. With plenty of free agent first basemen available, Williams could look for a short-term deal with someone like Derrek Lee, who knows all about playing in Chicago.

Closing the deal: Guillen has never been afraid to spar publicly with Jenks, so Ozzie's decision to remain with the White Sox will only add to the speculation that Jenks will be non-tendered or traded. Chicago could also look to keep free agent J.J. Putz, who revived his career in Chicago and set a White Sox franchise record of 27 straight scoreless appearances from May 14-July 28. Putz will not come cheaply, since several teams, such as the Braves and Diamondbacks, will be looking for closers. Even if Jenks remains, Putz has said being a full-time closer will not be the only factor in his decision. As of now, the plan is to move Chris Sale back to the starting rotation in 2011. If Peavy (shoulder surgery) returns to his old form, the Sox could be tempted to again make Sale a reliever to fortify the bullpen. —Doug Mittler, ESPN Insider

Organizational future

While third baseman Brent Morel has hardly lit things up in the big leagues, he'll likely go into next spring as someone to at least get a long look, as Omar Vizquel is unlikely to be a factor, and while Mark Teahen is signed through 2012, he can't stay healthy, doesn't hit much and more importantly is a horrible defender. A third-round pick in 2008, Morel is a plus (plus-plus for some) defender with a line-drive bat who hit .322/.359/.480 at the upper levels of the system this year. With an aggressive approach and slightly below-average power, he doesn't have the secondary skills to be a star, but he should be dependable, which is more than the White Sox got from the position in 2010. —Kevin Goldstein, Baseball Prospectus

A version of this story originally appeared on ESPN Insider Insider.