Lower the Jolly Roger. The ship is sinking.

“I knew we were in for a long season when we lined up for the National Anthem on opening day and one of my players said, ‘Every time I hear that song, I have a bad game.'” – Jim Leyland

Ahoy, mateys! Take a fun-filled journey through years a futility with me! Let’s see what treasures we can unlock in Davy Jones’ locker. Arrrrrgh!

As a Pittsburgh Pirates fan in my mid-twenties, I’ve been witness to some of the most mismanaged finances, contracts, and ballplayers in the history of baseball.  I’m going to take a trip down Memory Lane and look at some of my favorite Pittsburgh Pirate players and contracts over the last 20 years.  Other than the fact I think they’re the worst five contracts Pittsburgh has ever committed to, these players are in no particular order.  So settle down in your most comfortable chair and let’s take this journey from Family to Futility together.

5. Matt Morris (2007 – 2008)

Thank you for choosing to ruin your career in Pittsburgh. Enjoy your 13 million dollars in retirement.

Pittsburgh had the pleasure of employing Matt Morris after we dealt then minor leaguers Rajai Davis and Stephen MacFarland to San Francisco in July of 2007.

“Matt brings a veteran presence and durability to our rotation that should complement our current group of young starters,” Pirates general manager David Littlefield said about Morris.   If his plan was to make Pittsburgh Pirates starting pitching worse than it was, Mission: Accomplished.

The Matt Morris Project stemmed from Littlefield having some extra money to spend during the 2007 season.  The general sentiment around baseball was that super catching prospect Matt Wieters was going to be a Pittsburgh Pirate after the 2007 draft, as the buzz around him was pretty positive.  Littlefield’s inability to work and play well with Wieters’s agent Scott Boras and a philosophy that spending money on unproven talent was a waste, however, led him to not spending money in the draft on Wieters.  Instead Pittsburgh drafted another first round pitcher (one of the many first round pitching busts in Pittsburgh), Danny Moskos.  These are a few of the decisions that led to Pittsburgh ending up with Matt Morris.

Choosing to spend money to bring in Morris to help anchor the Pirates’ rotation,  Morris was guaranteed $13.5 million over the remaining two years on his contract.  Of the teams interested in dealing with San Fransisco, Pittsburgh was the only team willing to suck up the remaining $3.4 million for 2007 as well as the approximately $10 million for 2008, which instantly made Matt Morris the highest paid player per season in the history of the Pittsburgh Pirates.

During his tenure in Pittsburgh, Morris made 16 starts ($843,000 a start), compiled a record of 3-8, an ERA of 7.04 over 84.1 innings ($160,000 an inning).  He struck out 38 batters ($355,000 per strike out) and compiled a cringe-inducing WHIP of 1.75.  During his 16 starts in Pittsburgh, Morris raised his career ERA from 3.83 over 291 major league games, to 3.98 over 307.

Pittsburgh eventually cut ties with Matt Morris because of how terrible he was, which resulted in his retirement.  Needless to say, however, retirement at 33 probably didn’t seem so bad an option after those 16 games.

4. Jeromy Burnitz (2006)

A picture of Jeromy Burnitz that looks like it belongs on the Megan’s Law website.

In 2006 Pittsburgh signed 37 year old journeyman Jeromy Burnitz to a $6 million contract.  My blood pressure just spiked typing that.

Burnitz managed only 313 at bats for the Pirates that season, but somehow still managed to finish tied with Jose Bautista for second on the team in home runs with 16.  His .711 OPS finished behind the likes of single-smashing Sean Casey (.785), catcher Ronny Paulino (.754), and doubles machine Freddy Sanchez (.851).  He did beat out Joe Randa (.704), though.

He finished hitting .230 that season, which was low even by his already low standards (career .253 average).

Burnitz also had the nasty reputation for not hustling.  He was, however, appreciative to Dave Littlefield for paying him $20,000 per at bat.

3. Pat Meares (1999 – 2003)

A career on the decline signals full steam ahead for the Pittsburgh Pirates, which is why Pat Meares was such a great fit in the City of Bridges.  Signed as a 30 year old free agent for the 1999 season, Meares managed to hit .308 in 91 at bats before the DL hit him.  In management’s infinite wisdom, Pittsburgh signed Pat Meares to a 4 year, $15 million extension after that 91 at bat year.

His career as a Pirate was as follows:

823 AB, 17 HR, 79 RBI, .238 AVG, .647 OPS.  Oh, and he hit into 23 double plays as well.

He did also manage to steal one base, which meant that he was more successful at stealing bases (1-3) than he was at filing grievances against the Pirates (0-1) for supposedly keeping him on the DL while he was healthy.

Pat Meares did rock the mock turtleneck better than any other player on Pittsburgh’s roster.

2. Kevin Young (1992-1995, 1997-2003)

For years scouts referred to him as ‘the next Frank Thomas’.

Kevin Young is probably the most productive player on this list.  Unfortunately, that’s like saying you’re dating the hottest Hilton sister.  Not a lot to brag about.

My personal bias towards Kevin Young and how terrible I think he really was stems from watching him be the definition of ineptitude for a decade as a Pirates fan.  I watched him pop up to first basemen all season long at Three Rivers and then had the pleasure of him christening PNC Park with his anti-clutchness as well.  The fact that some scout dubbed him the ‘next Frank Thomas’ should make the Hall of Famer Frank Thomas throw up in his mouth.

From the time that Pittsburgh signed him to what was then the largest contract in team history in 2000 (4 years, $24 million.  Have you noticed a correlation between players who sign the largest contracts in our franchise history and productivity?), he did more damage than good in our lineup .  This was, of course, after both Pittsburgh and Kansas City had already cut him, which should be a pretty good indicator in and of itself that requisite baseball skills may be lacking.

All Kevin Young managed to do from 2000 until the end of his career in 2003 was have an average Rbat value of -9 (Rbat measures the number of runs better or worse than average a player is as a hitter).  I’m no sabermatician, but anything in the negatives in a counting sport like baseball probably isn’t good.

He did manage 1% of the vote for the National League MVP in 1997 though, so he had that going for him.

1. Derek Bell (2001-2002)

Quite possibly the greatest example of ineptitude in the history of professional sports, Derek Bell was handed a contract for 2 years and $10 million to help christen PNC Park in its inaugural year after posting pedestrian numbers his entire career.  Of course during the 90’s and early 2000’s, mediocrity was rewarded in Pittsburgh baseball, so Derek Bell seemed like a natural fit for the ball club as they transitioned into the new millennium.

The Crown Jewel of front office management in Pittsburgh.

In his first season in Pittsburgh, Bell managed to hit a mind numbing .173/5/13.  As a professional hitter, his batting average was lower than teammates Joe Beimel (.269), Jason Schmidt (.174), and Omar Olivares (.222), who were all professional pitchers.

It’s understandable after that performance, how one may think that Derek Bell’s job could have been in jeopardy going into the 2002 season.

Well, hopefully you didn’t tell Derek Bell that.

Not only did he feel that he belonged on a Major League roster after that disaster of a year in 2001, but he also felt that he should be a starting outfielder.  When questioned about his job security in spring training of 2002 and how he may have to compete for a job in the outfield, Derek Bell then went on what became my favorite rant in the history of professional sports:

“Nobody told me I was in competition. If there is competition, somebody better let me know.  If there is competition, they better eliminate me out of the race and go ahead and do what they’re going to do with me.  I ain’t never hit in spring training and I never will.  If it ain’t settled with me out there, then they can trade me.  I ain’t going out there to hurt myself in spring training battling for a job.  If it is [a competition], then I’m going into ‘Operation Shutdown.’  Tell them exactly what I said.  I haven’t competed for a job since 1991.”

After Operation: Shutdown, Pittsburgh cut ties with Bell during spring training of 2002.  Bell sailed off into the sunset on his houseboat with $4.5 million and a well documented, well developed a crack habit.

A true Pirate in every sense of the word.

Honorable Mentions

$7.75 million for Matt Lawton?  Seriously?  The only player in baseball history whose performance was negatively enhanced by performance enhancing drugs.  I hope that .273/10/44 was worth it, you ass clowns.

Akinori Iwamura, currently Pittsburgh’s highest paid player at $4.85 million, was optioned to Triple-A Indianapolis.

Jason Kendall.  6 years, $60 million.  Pittsburgh needed a face for their franchise.  His face was not the right one.  A terrible attitude in the clubhouse and the most expensive singles hitting machine in the history of baseball.

Jose Hernandez had a couple tours of duty in Pittsburgh.  He was paid per strikeout.  Which isn’t good, because he’s a hitter.

Pittsburgh was about a decade too late on Benito Santiago.

Raul Mondesi, you clever little minx.  Raul figured out how to get released by the Pirates, get signed by a contender, and get a raise in the process.  Another true Pirate, through and through.


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