Kiss’Em Goodbye: Pittsburgh Pirates

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 Pittsburgh Pirates, who seemed on track to end their streak of losing seasons before running out of steam down the stretch.

Baseball Prospectus' Take
Signs of hope: Andrew McCutchen has continued to mature into an up-the-middle star, finishing as the sixth-highest Wins Above Replacement Player (5.1 WARP) in the senior circuit, and 25-year-old outfielder Alex Presley made good on his 2010 breakout, tearing through Triple-A before putting up an .818 OPS in 180 plate appearances in Pittsburgh.

The Pirates still need to surround McCutchen with a more capable supporting cast, but a center fielder who excels in all aspects of the game is a player upon whom a team can build. While the club's 8-22 August ended any dreams of a respectable record in 2011, the Pirates did make a positive move for the future by spending big in the amateur draft. The organization set a major league record by dispensing $17 million to its picks, including $8 million to UCLA starter and first overall pick Gerrit Cole and $5 million to Josh Bell, a slugging high school outfielder who had slipped to the second round because he was believed to be destined for college.

While their payrolls at the major league level have lagged among the league's lowest, the Pirates have put their revenue-sharing funds to good use, spending a major league-leading $48 million in their first four drafts under GM Neil Huntington.

Signs of disaster: The Pirates' offense is tied with the Giants' for the lowest team TAv in the majors (.242), and their pitching staff has recorded the fourth-worst Fair Run Average (4.74) in the NL. The team clung to contention much longer than it has in most of its 19 consecutive losing seasons and remained two games over .500 through June, but that unanticipated success was built on a shaky foundation. To that point, the staff had posted a collective 3.50 ERA, but only an unsustainable .284 opposing BABIP had allowed its pitch-to-contact approach to succeed. Pirates pitchers have struck out 6.4 batters per nine innings, the lowest rate in a league that has fanned 7.3; since June, Pirates opponents have batted .320 on balls in play, and the team ERA has risen accordingly, to 4.35. The Pirates lack a single starter with the ability to miss many bats, which doesn't bode well for their future run prevention.

Signs you can ignore: The Pirates' youth movement appeared to be dealt a serious blow by the struggles of third baseman Pedro Alvarez, the 2008 second overall pick who burst onto the big league scene with 16 homers in 347 at-bats in 2010. In his sophomore season, Alvarez backslid to the tune of a .195/.262/.286 line and endured two Triple-A stints—the first of them successful, the second much less so. Coupled with a quad strain that sent him to the DL, Alvarez's poor offensive showing has made this something of a lost season, but his prospect pedigree, minor league track record and early success in the majors suggest that 2011 will be a blip along the way to stardom, not the beginning of the end. Still, he'll have to show a significant improvement in his plate approach in his age-25 season to restore his cornerstone status. —Ben Lindbergh, Baseball Prospectus

Bowden's Bold Move
After 19 consecutive losing seasons the Pirates need a couple of shrewd trades to help break the streak in 2012. The first bold move they should make is to try to trade for first baseman Yonder Alonso of the Cincinnati Reds. Alonso, 24, was the Reds' first-round selection (seventh overall) in the June 2008 free-agent amateur draft. Alonso hit .296/.374/.486 with 12 home runs at Triple-A Louisville this year before the Reds called him to the major leagues; however, he is blocked by Joey Votto at first, so he doesn't really have a position place in Cincy.

The Pirates should start by offering a package centered around outfielder Starling Marte, who is not only one of the best athletes in the Pirates' system, but would give the Reds a much-needed leadoff hitter. Marte is not enough to get Alonso straight up, but the Pirates do have some prospect depth to somehow make a deal work with Cincinnati. Alonso would give the Pirates another middle-of-the-order bat to build around Andrew McCutchen and Pedro Alvarez.

The Pirates should also pull the trigger on a six-year, $47 million dollar deal with their centerfielder Andrew McCutchen to send an important message to Pirates fans, while securing one of the team's leaders and best players. —Jim Bowden

Hopes and Fears
Best-case scenario ZiPS projection: 84-78
The Pirates made a lot of noise at around the halfway mark, and while the team wilted in the summer, they showed real flashes of being a contender. Despite a season that was better than many expected, Pittsburgh still has significant room to realistically improve on its 2011 campaign. The Pirates actually had very little good luck on offense—their best prospect, after all, has fought injuries and has an OPS around .550.

The team should get better offense out of catcher and third base and would have to put in a lot of effort to not improve at first base. Andrew McCutchen has an MVP year lurking in his bat, and Jose Tabata just turned 23 and still has a great deal of upside left. Add a better offense and a pitching staff that should be adequate, if not spectacular, and the Bucs have the opportunity to be even noisier next year.

Worst-case scenario: 66-96
As poor as the 10th-percentile projection for the Pirates is, their fans have seen much worse than a 66-win team in recent years. A lot would have to go wrong for the team, but given that the organization still hasn't built up a ton of depth at several positions, a few ill-timed injuries or disappointing years can really test that depth. When the team lost expected starters this year, they ended up having to go out and find an emergency catcher from the Red Sox in Mike McKenry and rush guys like Josh Harrison and Chase d'Arnaud.

With the team's fortunes on a rare upswing, one quiet thing the organization can't overlook this winter to prevent that pessimistic projection is to stash a few more veterans at Triple-A and be willing to use them as role players, rather than pushing their second-tier prospects too far, too quickly. —Dan Szymborski, Baseball Think Factory

Organizational Future
While the Pirates saw growth at the big league level this year, the same happened on the farm, but not enough to project anything more than a continued slow turnaround. While recent drafts have flooded the system with high-ceiling prospects, they're mostly of the young and inexperienced type, so 2012 will clearly be another year that falls firmly on the rebuilding side of the ledger. With recent first-round picks Gerrit Cole and Jameson Taillon, the Pirates are the envy of baseball in terms of potential front-end starters, and with the surprising signing of Josh Bell they've added a potential impact hitter, so now the challenge of development is firmly in their hands. However, it's still going to be another two or three years before it translates to elite big league success. —Kevin Goldstein, Baseball Prospectus

A version of this story originally appeared on ESPN Insider .