Pittsburgh Pirates Passed on These Players in Post-1992 MLB Drafts

The Pirates woes are well documented. They have not had a winning season since 1992. Francisco Cabrera, Sid Bream, skinny Barry Bonds, we all know the characters.

But before anyone blames their woes on small markets and unfair payroll disparities, remember the A's and the Ray's put a team in the playoffs eight out of the past twelve years.

And neither of those teams play in a tax payer funded gem of a park like PNC Park.

One of the biggest culprits of the Pirates' continued futility is their failure to develop stars through the draft. Since the 1992 NLCS, the Pirates have had 22 first round and compensation picks, and 12 times they have picked in the top 10. They had the first overall pick three times, and despite having quality picks, those selections have yielded one legit star—Andrew McCutchen—and a few players who never made the majors.

Any team can make a bad selection from time to time, but to whiff that consistently brings up an agonizing line of questioning. Who did the Pirates pass up?

It is too early to tell if their 2008, 2009, 2010 and 2011 top picks are busts or not; Pedro Alvarez, Victor Black, Tony Sanchez, Jameson Tailon and Gerrit Cole could all pan out.

Here are players who were available when the Pirates made their first picks from 1993 to 2007 that were snatched up before the Pirates made their second picks.

Close your eyes, Pirate fans. These players could have worn the black and gold.

Scott Rolen: 1993

In the first draft after the 1992 NLCS, the Pirates picked three times in the first round.

Outfielder Jermaine Allensworth would end up playing four seasons in the major leagues.

But Outfielder Charles Peterson and first baseman Charles Rice never made it to the show.

Four picks after Rice, the Phillies chose Scott Rolen. Still playing in his 17th season, he has been a Rookie of the Year and eight time Gold Glove winner, a Silver Slugger, a seven time All Star, a post season hero and a 4th place winner in the 2004 NL MVP vote.

He would be a good mentor to Pedro Alvarez now.

Paul Konerko: 1994

In 1994, the Pirates drafted shortstop Mark Farris 11th overall. He never made it to the major leagues.

Two picks later, the Dodgers selected Konerko. A fixture in Chicago for the past 14 seasons, he remains an MVP candidate while slugging over 400 career homers. He was also a playoff hero in all three rounds the White Sox won the 2005 World Series.

Think his quiet, classy yet consistent play would have gone over well in Pittsburgh.

Nomar Garciaparra was picked right after Farris, but Konerko gets the nod here because he is still playing.

Roy Halladay: 1995

The Pirates picked 10th overall in 1995 and once again selected a shortstop. Chad Hermansen eventually made it to the major leagues, but his time in the show ended in 2004 after six seasons.

Meanwhile Halladay, picked 17th overall by Toronto, is still active (although on the disabled list as of this writing). He has two Cy Youngs, one from each league, on his mantle and five additional top five Cy Young finishes. He has notched 192 wins with a post season no hitter to his name.

And of course he has been winning big games in Pennsylvania recently. Just on the other side of the state.

Jimmy Rollins: 1996

The Pirates had the top pick in 1996 and selected Kris Benson who had a nice but unmemorable career. He is best known for having a beautiful if (eccentric and media obsessed) wife.

To be fair, the first round of the draft did not yield many superstars. Braden Looper, Billy Koch and Eric Chavez were all picked in the first round—they had nice careers, but they were not stars.

The Pirates had made two selections by the time the Phillies drafted Rollins 46th overall. Rollins has given the Phillies more than twelve seasons of solid play. The 2007 NL MVP has been a Silver Slugger as well as a multiple Gold Glove winner. One of the key members of Philadelphia's five straight Division titles, he won Game 4 of the 2009 NLCS with his walk off single.

Once again, a player who brought glory to one side of Pennsylvania instead of the other.

Lance Berkman: 1997

The Pirates had the number 8 pick in the 1997 draft and used it on J. J. Davis. He played in 67 games over four seasons and had one career homer.

The Astros drafted Lance Berkman with the 16th pick. He hit 359 homers over 14 seasons and lead the National League with 128 RBIs in 2002. He finished in the top 10 five times for the MVP vote, including last season with St. Louis. He saved the Cardinals from elimination with his two out, two strike RBI single in the 10th inning of 2011 World Series Game 6. He has a career average of .296 with an OPS of .955.

And he has the reputation of being one of the good guys and hardest workers in the game. Again, he would have been beloved in Pittsburgh.

CC Sabathia: 1998

The Pirates had the 15th overall pick in 1998 and went for a left-handed pitcher. Clint Johnson was drafted out of Vanderbilt. He could never get out of single A ball after three seasons. He would become a first baseman and played for many years in Single A and the Independent Leagues before peaking in AA.

Meanwhile the Indians had the 20th pick and drafted Sabathia. He won a Cy Young in Cleveland, basically willed Milwaukee to the post season in 2008 and win the 2009 ALCS MVP with the Yankees, getting his first ring.

One of the legit aces in the game, he is also one of the most likable characters in the game pitching his way potentially into Cooperstown.

He can hit too. If the Pirates wanted a left-handed pitcher who could hit, they should have just drafted Sabathia.

Barry Zito: 1999

In 1999 the Pirates used the number eight pick to select Bobby Bradley, who never made it to the majors.

Zito was selected with the number nine pick. He has been maligned in his first five disappointing seasons in San Francisco, but he won the 2002 AL Cy Young Award with Oakland and consistently topped 210 innings a season. He is currently making a comeback with a fine 2012 season.

Sure, his laid back crunchy personality might not go over in Pittsburgh like it did in Oakland, but if he kept winning, Pirate fans might actually take up healthy eating and yoga.

Adam Wainwright: 2000

The Pirates had the 19th pick of the 2000 draft and picked left-hander Sean Burnett. After missing all of the 2005 season due to injury, he developed into a decent relief pitcher. He is having an excellent 2012, posting a .054 ERA over 16 relief innings. Unfortunately for the Pirates, he is doing that for the Washington Nationals. (To be fair, the Pirates acquired All Star closer Joel Hanrahan in the deal for Burnett.

Meanwhile the Braves tapped Wainwright and then shipped him to St. Louis in the J. D. Drew trade. Wainwright became the emergency closer in 2006 when Jason Isringhausen went down to injury. He closed out the Division Series, the NLCS and the World Series, most memorably getting Carlos Beltran to strike out looking to clinch the pennant.

As a starter, he finished third in the 2009 Cy Young vote and was the 2010 Cy Young runner up before injuries wiped out his 2011 campaign.

David Wright: 2001

The Pirates had the number eight pick in 2001 and used it to draft pitcher John Van Benschoten from Kent State. He wound up playing over three different seasons with the Pirates (2004, 2007 and 2008), finishing with a 2-13 record and a 9.20 ERA. But unlike a lot of Pittsburgh's first rounders, he actually made it to the major leagues.

David Wright has become the best home grown third baseman in Mets history. He combines power with solid hitting, a flair for the dramatic and is probably the most popular Met since Mike Piazza. After an injury plagued 2011, he has the Mets near the top of the standings and is having his best season in years.

Prince Fielder: 2002

The Pirates had the pick of the entire litter 2002, and they drafted pitcher Bryan Bullington. He pitched in 26 games over five seasons, and his final career win total was 1.

Bullington is considered to be one of the biggest disasters in the history of the MLB Draft.

There was no shortage of future big talents in the draft: Zack Greinke, Nick Swisher, Cole Hamels and Matt Cain were all there.

But no talent would have been more intriguing in PNC Park than the mighty Prince Fielder.

He has the power to hit 50 home run, hits for a high average and OPS and is larger than life in all facets of his game. The Pirates already had the left-handed hitting son of a former star on their team once with Barry Bonds, so Fielder would have probably been more embraced by the fans than Bullington.

Aaron Hill: 2003

The number eight pick belonged to the Pirates in 2003, and they selected left-hander Paul Maholm. To be fair, this was not a terrible pick. He never got much run support, but he pitched well in Pittsburgh for much of his six and a half seasons with the Pirates.

The Blue Jays nabbed Aaron Hill with the 13th pick, meaning Toronto got an All Star second baseman who cracked 36 homers in 2009. In 2011, he was dealt to Arizona where he homered in the Division Series as a member of the Diamondbacks.

Jered Weaver: 2004

The Pirates held the 11th pick of the 2004 draft and used it to grab high school catcher Neil Walker. He was a Pittsburgh native and his arrival in the Pirates organization was a feel good story. Somewhere between draft day and today, he turned in his catchers gear and became a second baseman.

He is actually one of the better Pirates picks. A Rookie of the Year contender in 2010, he gives the Pirates some pop and a decent bat at second base.

But it is hard to not wonder what could have been with Weaver in Pittsburgh, who was chosen by the Angels with the very next pick. The Cal State Long Beach star was an 11 game winner just two years after being drafted. He finished fifth in the 2010 Cy Young vote and was the Cy Young runner up in 2011. He threw in a no hitter for good measure this year, and when healthy, is one of the elite pitchers in the game.

He is hurt now, but is signed through 2016.

Tim Lincecum or Clayton Kershaw: 2006

2005 is skipped because the Pirates selected Andrew McCutchen, who has proven to be an excellent pick.

The Pirates had the fourth pick of the 2006 draft and chose University of Houston starter Brad Lincoln. Injuries cost him his 2007 season in the minors, and his first few years in the majors were not effective. But he has found a home in the Pirates bullpen, keeping the opponent scoreless for 12 of 14 appearances.

As nice as it is to have an effective reliever, a Cy Young ace is even better. Tim Linecum won the National League Cy Young in 2008 and 2009 and led the Giants to the 2010 World Series title. Clayton Kershaw won the Cy Young in 2011.

Take your pick. The Pirates could have.

Madison Bumgarner: 2007

The Pirates picked fourth in 2007 and brought in a left-handed pitcher Daniel Moskos. He pitched well as a reliever for the 2011 Pirates and is still in the Pirates farm system.

Meanwhile the San Francisco Giants got Madison Bumgarner with the 10th pick. Recalled at the end of the 2009 season, he provided some post season heroics on the 2010 squad. He was the winning pitcher for the clinching Game Four of the Division Series against Atlanta, and then he pitched eight brilliant shut out innings in Game Four of the 2010 World Series against Texas to bring San Francisco to within a win of the World Series title.

He was twenty years old.

Yet another arm that could put the Pirates over the top.