Pittsburgh Pirates: All Time Overpaid Starting Lineup


Hello, all. Welcome to a new series of mine. In this series, I will be making some all-time lists based on the history of our beloved Pittsburgh Pirates. These will not be your typical lists (i.e, ‘”Top 10 shortstops in Pirates history), but rather, I will be diving into more unconventional waters. I will be starting off by going into what I think are the most overpaid Pirates players by position. In case you’re slow to pick up, that means I will be writing about past Buccos who were paid a hefty amount of money, but did not perform up to their bank account. Let’s get into it

Pitcher- Matt Morris

Acquired via trade with the San Francisco Giants, July 31st 2007

How expensive: Pirates took on Morris’s $10,000,000 salary 

How badly did he under perform: Never won a game in a Pirates uniform, retired after being released by the team in April of 2008

I’ve met David Littlefield on a few occasions. He is a polite and decent human being. However, he did not do a whole lot of good for the Pittsburgh Pirates Baseball Club, and acquiring Matt Morris was the icing on a cake that was made of crap and cigarette ash that took 6 years for the organization to digest. There was no logical reason for the Pirates to trade for Matt Morris. Sure, he had been a very good pitcher earlier in the decade for Tony La Russa’s Cardinals, but when the Pirates traded for him, Morris was 33 years old and carrying a record of 7-7 with an ERA of 4.35, and his last good year was all the way back in 2003 with the St. Louis. The Pirates were well out of the pennant race and had no use for a mediocre veteran, especially won with a $10,000,000 price tag. If things didn’t seem bad enough, the Pirates gave up a promising outfield prospect in Rajai Davis, who has turned in a nice MLB career that is still ongoing with the Cleveland Indians. The only positive thing Morris accomplished in Pittsburgh was hitting a home run in his first start as a Pirate (I happened to attend that game). It was all downhill from there, as Morris finished his Pirate career with a record of 0-4, earning himself a ticket out-of-town early in the 2008 season and promptly retiring soon after his release.

As bad a Morris’s time in a Pirate uniform was, he lasted longer upon his arrival than Littlefield, who was fired less then two months after making this head scratcher of a deal. The only sense that can possibly be made of the Morris deal is that it was a last ditch attempt by Littlefield too win a few more games and give himself a fighting chance at sticking around for another year. It’s safe to say things may have backfired a little on King David.

Catcher: Jason Kendall

Signed a 6 year, $60,000,000 contract extension with the Pirates on November 18th, 2000

Obviously, Jason Kendall was not a scrub. He is one the greatest catcher in franchise history, so you can understand what Pirates management was thinking after the 2000 season when they gave Kendall what was, especially at that time, a massive contract extension. Kendall was still a young man at 26 years of age, and had established himself as a franchise cornerstone since breaking into the majors with the Pirates in 1996. The Pirates knew they weren’t a very good team and knew that their bank account would not allow them to real in any major free agents, but they were hoping for something that would excite their fan base upon moving into PNC Park. So, they decided to lock up their very popular catcher long-term.

However, there were red flags right away. In late 2000, Kendall was over a year removed from what is the most notorious injury in club history; a broken ankle suffered when Kendall ran out a bunt at Three Rivers Stadium. http://old.post-gazette.com/images/19990705apkendallfirstM.jpg. Although Kendall was an All-Star in 2000, the cold hard fact was that the Pirates did not have a lot of money, and should not have been in the business of offering up hefty contracts. Although Kendall remained one of the Pirates few assets until being traded to Oakland after the 2004 season, he was never again an All-Star and could never live up to what the Pirates were paying him. To this day, Jason Kendall’s contract is the highest in Pirates history.

First Baseman: Kevin Young 

Signed a 4 year, $24,000,000 extension in March of 1999.

Cam Bonifay liked to overpay, and if you haven’t noticed that by this point, you will by the time this article is complete. In the late 90s, Kevin Young was in his second stint with the Bucs, and things were going pretty well for him. In 1998, he had his best season to that point, batting .270 with 27 dingers, 108 RBI and an OPS of .809 as part of the Pirates “bomb squad”. After receiving his extension, Young performance increased in 1999, as he raised his OPS by 100 points while posting similar homer and RBI totals. As the millennium turned, however, so did Youngs fortunes, and his performance  steadily decreased until his retirement after the 2003 season.

Paying KY the big bucks dosent look like an awful idea considering the player that he was for a brief time, but he did not perform up to his lofty bankroll, and for that, he deserves to be here.

Second Baseman: Aki Iwamura 

Acquired in a trade with the Tampa Bay Rays on November 2nd, 2009, earning $4.85 million for the season

How badly did he under perform: Hit .182 with just 2 home runs and 9 RBI, could not get base, had no range at second base, the pro typical 1992-2012 Pittsburgh Pirate

The first player that Pirates fans should, and probably do, think about in regards to the franchise turning the corner over the past 3 seasons is Andrew McCutchen. The first player the Pirates should think about in regards to the Pirates historic 20 year losing season streak may very well be a man who showed no redeeming qualities as a player while he was here. A man who somehow managed to stick out like a sore thumb as the most futile player on a team that was on it’s way to losing 105 games. A man who couldn’t hit, couldn’t run, couldn’t hit for power, couldn’t field and couldn’t throw. Yes, this man was Aki Iwamura.

Amazingly, I do not blame Neil Huntington for bringing Aki to Pittsburgh. The Pirates were looking for a second baseman to replace the immensely popular Freddy Sanchez, and Iwamura seemed like a reasonable choice. Iwamura played a big role in getting the Rays to the World Series in 2008, and in an injury riddled 2009 season, he batted .290 and had a respectable OPS of .745. The player who the Pirates were sending to Tampa in return, relief pitcher Jesse Chavez, was nothing special, so it looked like the Pirates made a decent baseball decision. However, things went sour real fast. I’ve written a lot of Aki’s major statics above, and one that I did not throw up their was that his slugging percentage while in Pittsburgh was .267. That’s right. Aki’s SLUGGING percentage was lower than Andrew McCutchen’s batting average. I know nothing about what Aki is like as a person, but I sure hope he’s a better human being than he was a second baseman.

Shortstop: Pat Meares

Signed a 4 year, $15,000,000 extension with the Pirates on April 30th, 1999. 

What do you do with a 30-year old short stop who never hit .300, never had an On-base percentage above .323, only hit 10+ home runs twice in the steroid era, and once led the league in fielding errors at his position? If your Cam Bonify, give him a long term extension, of course. The Pat Meares contract extension defied all logic. It was horrifying. Meares came to Pittsburgh as a free agent from the Minnesota Twins before the 1999 season, and his original $1.5 million dollar deal seemed innocent enough. But after just one month of the season had gone by, the Pirates jumped the gun and offered Meares this mind-boggling extension. Less than two weeks after signing the extension, Meares took a fastball to the hand and was forced to miss the remainder of the season. Meares played two more years with the Bucs, hit .211 in his last, and was released. A lot can be said negatively about Dave Littlefield’s time as Pirates GM, but he never made contract signings that were as awesomely stupid as the ones Bonifay handed out on a fairly regular basis.

Third Baseman: Joe Randa 

Signed as a free agent from the San Diego Padres on December 28th, 2005, for a one-year contract worth between $4.5 and $5 million. 

How badly did he under perform: Played in just 89 games, OPS of just .704 with 4 home runs, retired after the season

This is probably the least overpaid player in my starting lineup, but Joe Randa was still overpaid nonetheless. ”The Joker” was a popular player in his first stink with the Bucs in the ”Freak Show” year of 1997, and he had a decent season in 2005, splitting time with the Cincinnati Reds and San Diego Padres. The problem with this signing was that Randa was 36 years old and going to a team that needed to get young. In the end, Randa helped create the Pirates youth movement by going on the DL and making way for Freddy Sanchez, who wound up winning the NL Batting Title. ‘”The Joker” retired after the 2006 season, and nobody in Pittsburgh seemed to notice.

Outfielders: Derek Bell, Jose Tabata and Jeromy Burnitz 

True story. In May of 2006, I was at PNC Park watching the Bucs battle the Houston Astros. Our seats were along the first base side, very close to Bucco right fielder, Jeromy Burnitz. This one gentleman in front of us hated Burnitz. Like, not the innocent 7-year old who won’t eat brussel sprouts type of hate, but more like the hate you would have for your neighbor if he purposely ran over your dog with his Jeep. The guy was riding Burnitz the hole game, and it got to the point where another gentleman who was sitting above the Clemente Wall was able to hear him and started yelling back at the angry fan. This isn’t a fully accurate transcript of the conversation, but it went a little something like this:

Peacemaker: Aren’t you supposed to be a Pirate fan?

Angry Guy: I like the Pirates, I just hate Burnitz. He’s being paid $5,000,000 and he’s doing nothing!

Jeromy Burnitz, under his breath: It’s $6,000,000

Jeromy Burnitz came to Pittsburgh on a 2 year contract worth $12,000,000 in January of 2006, and his story is similar to that of Joe Randa: Decent enough player, but really old! Burnitz proved to be  a waste, batting just .230 with 16 homers and 49 RBI and an OBP under .300. The Pirates chose not to keep Burnitz around after the season, and he never played another inning in the majors.

If you are a regular reader of this website, you probably care enough about the Pirates to know the story of Derek ”Operation Shutdown” Bell, so I will not retell it due to fear of redundancy. Long story short, he was trash.

Jose Tabata is an interesting case. His Pirates career started off oh so promising, as he hit .299. Tabat’s potential was such that when the Pirates decided to sign him to a 6-year contract worth $14.75 million dollars. In 2012, Tabata’s play suffered, and many Pirate’s fans grew critical of his effort and weight gain. For the rest of his time in Pittsburgh, Tabata performed well when he was allowed on the field, but for whatever reason, could never get himself out of Clint Hurdle’s doghouse, and could never get comfortable in the Pirates starting lineup. In 2015, after playing second fiddle to the likes of Jaff Decker, Tabata and his contract were shipped to LA. Tabata’s career has been a appointment’s, but part of that is due to  lack of opportunity.