Kiss 'Em Goodbye is a series focusing on MLB teams as their postseason dreams fade — be that in September (or before) or in the LDS, LCS and World Series rounds. It combines a broad overview of the past season from Buster Olney, a take from Baseball Prospectus, a look towards an immediate 2011 move courtesy of Rumor Central, and Kevin Goldstein's farm system overview. You can find all teams on one page by going here.

Here now: the Chicago Cubs. It's time to kiss 'em goodbye.

The Overview

Blessed with a relatively easy schedule at the outset of the season, the Cubs collapsed right at the start—opening 15-22—and they never recovered. Derrek Lee struggled early, Aramis Ramirez batted .152 in April and .173 in May, and the bullpen problems were so acute that Lou Piniella felt compelled to shift Carlos Zambrano into a relief role—and that seemed to feed into the explosion that Big Z had in the middle of the season. Piniella announced his intention to retire and then stepped away in August, and the Cubs, just a couple of seasons removed from 2008, when they dominated the National League, were left to consider a major overhaul.

There's good news, though; Starlin Castro has competed for a batting title and established himself as a big-league shortstop even before he can drink legally. Carlos Silva stunned the baseball world with his strong first half after being dumped by the Seattle Mariners, and Carlos Marmol averaged almost two strikeouts per inning in his first full year as the Cubs' closer.

GM Jim Hendry must identify a new manager, and the Cubs must determine whether Zambrano's late-season surge is reason enough to expect that his anger management counseling has helped him turn a corner. The Cubs need a first baseman to replace Lee and a starting pitcher to step into Ted Lilly's spot. They will wait to hear whether Ramirez is going to pick up his $14.6 million option for 2011; given the need to get out from under too many crippling contracts (Alfonso Soriano, Zambrano) the Cubs would probably be thrilled if Ramirez walked away.—Buster Olney, ESPN Insider

Baseball Prospectus' take

What went right: Castro was great; another rookie, outfielder Tyler Colvin, became a power source. Geovany Soto bounced back to his Rookie of the Year from of 2008 after an awful sophomore season. Kosuke Fukudome finally lived up to the hype in his third season after coming over from Japan and became a source of on-base percentage. Marlon Byrd proved to be a good free agent signing; he was selected to play in the All-Star Game.

The key number: 19. That's how many rookies the Cubs used this season, including 13 pitchers. In 134 years of Cubs baseball, they had never used that many rooks.

What went wrong: After starting the season with hopes of contending for the division title, the poor start really hurt them—the Cubs eventually went into retooling mode as they traded Lilly, Lee and Ryan Theriot and Mike Fontenot.

What won't happen again: The Cubs won't be as reliant on veterans as they have been in recent years. While general manager Jim Hendry will have a hard time moving the big contracts of Zambrano and Soriano this winter, the Cubs will continue to look to get younger and are also likely to have new blood on the bench: Hall of Famer and Cubs legend Ryne Sandberg is the heavy favorite to replace Piniella after being named Manager of the Year in the Pacific Coast League with Triple-A Iowa.—John Perrotto, Baseball Prospectus

Rumor Central: On 2011 options

The Rumblings: Some believe Ramirez would do the club a favor and decline the $14.6 million dollar player option he holds for 2011; overall, though, don't count on that happening. As mentioned above, Zambrano has lately been pitching to his contract, which leaves the Cubs with mixed feelings: if he's pitching well sans the shenanigans, Z is a frontline starter; he's also more attractive trade bait. The bet within the rumor mill is he'll be back; that would provide another answer in a rotation that isn't likely to be buttressed with a big signing. More likely: Look for Jeff Samardzija to get another shot.

A Move That Could Work: One of the more quizzical moves of the trade deadline wasn't a move at all. Adam Dunn was rumored to be traded to numerous places—and very closely linked with the Chicago White Sox—but ultimately, the Nationals decided to hold onto their Bunyanesque slugger. Good for the Cubs. After parting ways with Lee, if the Cubs are willing to give Dunn a four-year deal—and he would have signed with Washington if it'd offered that—they have a great shot to get him. Dunn still wants to play in the field, so an NL team without the option to DH him will fit, and he's made no secret about his affection for playing in Chicago.—Chris Sprow, ESPN Insider

Keep up with Rumor Central year-round here.

Organizational Future

The Cubs' system, known more for its depth than star power, has little impact talent to offer the 2011 squad. That said, 2009 first-round pick Brett Jackson could be patrolling the Wrigley Field outfield at some point during the season. While he slowed down a bit at Double-A after a blistering first half in the high-A Florida State League, Jackson's power/speed package—along with good defense—should make a difference, although strikeouts will always prevent him from hitting for a high average.—Kevin Goldstein, Baseball Prospectus

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