Kiss 'Em Goodbye is a series focusing on MLB teams as their postseason dreams fade—whether in September (or before), the 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.
It was a fantastic regular season for the Philadelphia Phillies, a team with one of the best pitching rotations in history. However, you have to score runs, which they didn't, and it's time to say farewell.
Signs of hope: The Phillies won 102 games on the strength of a deep starting rotation that hosted two former Cy Young Award winners in Roy Halladay and Cliff Lee, two other former All-Stars in Cole Hamels and Roy Oswalt, and a candidate for rookie of the year in Vance Worley. Phillies starters led the majors in fair run average (3.55), a figure that was last equaled by the 1992 Braves and not surpassed since the 1988 Mets. After some hunting for a closer, longtime bullpen inmate Ryan Madson stabilized the relief endgame with a 94 percent save conversion rate.
The offense was unremarkable, something that became painfully obvious in the postseason, but trade deadline acquisition Hunter Pence blossomed upon arriving in the City of Brotherly Baseball, hitting .324/.394/.560, and prior to a slow September, center fielder Shane Victorino's season had some fans whispering "MVP."
Signs of disaster: The Phillies are so old that they're the official MLB team of the AARP. With the exception of the three primary right fielders (Domonic Brown, Ben Francisco and Pence), every regular was 30 or older. Worse, the Phillies have arranged to be stuck with some of their declining oldsters. Most egregiously, in April of last year, GM Ruben Amaro Jr. extended first baseman Ryan Howard's contract roughly two seasons before he had to, issuing him a five-year extension that might as well be six years given the poison pill of a $10 million buyout on a 2017 option, when Howard will be 38 years old. Howard, who hit .253/.346/.488 with 33 home runs, is a good-not-great hitter for a first baseman—he has not ranked in the offensive top 10 at his position since 2007—and a poor fielder and baserunner. The latter two qualities mean that his offensive contributions are heavily discounted, qualities that will become more extreme as the Phillies pay him another $125 million. If Howard's injury on the last at-bat of the National League Division Series keeps him out for a significant part of 2012, the decision becomes that much worse.
Signs you can ignore: Relief southpaw Antonio Bastardo was ridiculously effective, holding batters to .144/.242/.282 rates on the season. In doing so, he benefited from a .182 batting average on balls in play, a success rate that will revert to the league average. It's not a question of if but when. The course correction began in September, when Bastardo was pounded for nine runs in 7.1 innings, and there is more punishment where that came from. Though Bastardo is only 26 years old, and therefore a rare younger talent in an organization full of graybeards, they might be wise to trade Bastardo now, at the peak of his value. —Steven Goldman, Baseball Prospectus
Bowden's Bold Move
The Phillies' exit in the first round of the playoffs was certainly a disappointment to their front office, especially after last offseason's acquisition of Lee and the in-season deal for Pence.
The Phillies are expected to let Raul Ibanez leave via free agency, replacing him in left field with Brown and John Mayberry Jr. They hope to re-sign Madson, Jimmy Rollins, and Oswalt, although it will be a financial struggle.
The bold move I would make is to try and keep the team together for another run next year while strengthening and lengthening the bullpen. There are several top relievers that will be on the free-agent market, including Jonathan Papelbon, Heath Bell, and Francisco Rodriguez. Adding a proven, experienced arm (or two) to help with innings seven through nine would really add something to this team. —Jim Bowden
Hopes and Fears
Best-case scenario ZiPS projection: 99-63
As of now, the Phillies rotation is still together, and if they can bring back Rollins and keep healthy, the offense can start pulling its weight again—despite winning 102 games, the hitting was only average. A full season of Pence and Brown is as good as any non-Pujols/Fielder signing and should be enough to counteract the aging of some of the Phillies' stars. No surprises on the upside, as we've seen what the rotation can do.
Worst-case scenario: 83-79
The Phillies have enough outfield depth to handle injuries and disappointments, but the team's infield reserves are paper thin. The return of Rollins is probable but not assured, and there are really no practical alternatives in the system for any of the infielders. There's not much at catcher behind Carlos Ruiz, either. The depth is better in the rotation with Kyle Kendrick and Joe Blanton still around, but one of them may have to replace Oswalt, as there's a good chance that the Phils will decline his $16 million option. There's too much talent to worry about disappointments dragging the team down. If anything takes down the 2012 Phillies and gives the division to the Atlanta Braves, it'll probably be injuries. —Dan Szymborski, Baseball Think Factory
Organizational Future
The Phillies no longer have a strong system. In many ways it's for the right reasons, as prospects have been used to acquire key components, such as Oswalt and Pence, for playoff teams. It's time to find a way to finally get Brown into the lineup, and while everyone knows Brown's name, the lesser-known prospect who might be more important is Freddy Galvis. A slick-fielding shortstop from Venezuela, Galvis could become one of the most important players on the squad should Rollins depart via free agency. Seen as a glove-only type, Galvis hit .278/.324/.392 at the upper levels while setting career highs in nearly every offensive category. While he still projects to hit eighth in an NL lineup, at least he projects to play every day. —Kevin Goldstein, Baseball Prospectus
A version of this story originally appeared on ESPN Insider 
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As for Wright, 3B is the obvious upgrade spot. But why give up a ton for Wright (to a division rival, no less) when Aramis Ramirez is a free agent? Ramirez plans to decline his $16M option because he wants to play for a contender, and says he's not sure how much longer he's going to play. That sounds like a great candidate for a 3 or 4-year deal from the Phils. He's amazingly consistent (other than his injury-plagued 2010) and plugs the power void left by Howard for much of next year.
Of course, signing Ramirez means letting Rollins go, but at this stage of their careers, I'd rather have Ramirez/Galvis on the left side than Polanco/Rollins. The Ramirez signing also fixes the infield-depth issue that Szym noted, as Polanco moves into a super-sub role and gets starts at 2B when Utley slides to 1B (Utley will split time there with Mayberry until Howard returns).
Playing the kids would be bold. Brown/Mayberry (LF), Galvis (SS), and Aumont (closer) are ready. Let 'em play!
There is no combination of players that would make the Nats trade him to the Phillies.
If they could sign A. Ramirez for 2-3 years, they should do it.
Dreaming of what could have been: if only Amaro hadn't extended Howard (a move I deplored at the time), they could have allowed Ibanez and Howard to walk, and used the money to make a play for Fielder or Pujols. THAT would have been nice.