Like all Major League Baseball teams, the Pittsburgh Pirates have entered into their fair share of good and bad player contracts. Long-term contracts are inevitably and inherently risky for both the team and the player. With hindsight being 20/20, here’s one man’s opinion on the five worst contracts in Pirates history. This will include both free agent contracts and contract extensions.
Pirates Have Entered into Some Bad Contracts
5. California Dreaming
On April 1, 1981, the Pirates traded their fighting catcher Ed Ott and minor league pitcher Mickey Mahler to the California Angels to obtain Jason Thompson, a slugging, left-handed hitting first baseman. Thompson was immediately flipped to the New York Yankees for Jim Spencer, an older, left-handed hitting first baseman, and two young pitching prospects. Oh – and the Yankees threw in $400,000. That’s the part baseball commissioner Bowie Kuhn didn’t like.
Using his self-proclaimed authority to veto trades involving excessive cash amounts as “not in the best interests of baseball,” Kuhn vetoed the Pirates/Yankees deal. Unable to restructure the deal to Kuhn’s liking, the Pirates would keep Thompson.
Unfortunately, that was after Pirates general manager Hardy Peterson and chief scout Howie Haak said the quiet part out loud. Justifying dealing Thompson for Spencer, Peterson told Charley Feeney of the Pittsburgh Post-Gazette, “First, Spencer is an outstanding fielding first baseman and Thompson isn’t. Second, Spencer hits left-handed pitchers better than Thompson.” Added Haak, “Spencer is a pull hitter and Thompson hits to the long part of most ballparks.”
“I’ll Always Be Bitter”
As a result, the sensitive Thompson felt unwanted. It showed in his performance. In the strike-shortened season, he hit just .242/.396/.502, 15 HR, and 42 RBI. On September 6, Thompson told Dan Donovan of The Pittsburgh Press that he was bothered by his situation in Pittsburgh. At the time, Thompson was hitting .186/.343/.365. “I’m bitter and I guess I’ll always be bitter,” he said.
However, a few million dollars can cure a lot of bitterness. With free agency looming, Thompson had a career year in 1982. He hit .284/.391/.511, 31 HR, 101 RBI, and 147 OPS+ while accumulating 4.7 WAR. That earned him a five-year, $5.5 million deal to remain with Pittsburgh. It may not seem like much in today’s era of bloated contracts, but at the time it was the biggest contract in Pirates history.
Alas, Thompson never lived up to it. From 1983-85, he hit .252/.367/.392, 47 HR, and 211 RBI. His home run numbers steadily declined, from 18 in 1983 to 17 in 1984 to 12 in 1985. Four of his 1984 homers came in an afternoon doubleheader at Wrigley Field.
“Pretty Unbearable”
The quiet, overly sensitive, laid-back Californian never fit in the former steel town. Given Thompson’s issues during the 1981 season, Peterson was dreaming if he thought it could be otherwise. Fans accustomed to the free-swinging Pirates of Dave Parker and Al Oliver were frustrated watching Thompson take pitches over the heart of the plate with men on base. Seemingly every time Thompson connected with a mistake pitch, true to Haak’s 1981 assessment, the result was a fly out to the center field warning track. When the Pirates finally traded Thompson in the spring of 1986, he opened up to Bob Hertzel of The Press. “Last year was torture,” said Thompson. “The whole scene. I took a lot of unfair abuse. It was pretty unbearable.” Two months later, Thompson’s career was over after he went 10-for-51 in 30 games with the Montreal Expos.
4/4/86
The Pirates trade the enigmatic Jason Thompson to the Expos. Thompson hits .196 in 30 games for Montreal and is released in July.
Here is the rest of the action for April 4th in 1980s Baseball: https://80sbaseball.com/april4/— J. Daniel (@jdaniel2033.bsky.social) April 4, 2024 at 6:15 PM
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4. The Kid
Jason Kendall was born in the right year. Pirates general partner Kevin McClatchy had lobbied hard for the construction of PNC Park, which finally became a reality in 2001. McClatchy argued that, inter alia, the new ballpark would allow the Pirates to retain their talent. Kendall’s case was the first to arise and allow McClatchy to put his money where his mouth was. At that point, “The Kid” was the Pirates’ best player. In his first five seasons from 1996-2000, the right-handed-hitting catcher hit .314/.402/.456, accumulated 20.0 WAR, and was a three-time All-Star.
For that, he was rewarded with a six-year extension worth $60 million in November 2000. The deal took effect in 2002 and was the largest contract the Pirates ever gave. It still is. Said McClatchy to Robert Dvorchak of the Post-Gazette, “This sends a message that we are serious about winning.”
Including Kendall’s deal among the worst contracts in Pirates history will likely be as polarizing as Kendall himself was. His old-school approach on the field was popular with the fans. He played hard, got his uniform dirty, and played hurt. He worked hard to bounce back from what appeared to be a devastating, career-ending ankle injury.
A Bad Teammate
But he was also at the center of a dysfunctional clubhouse where the more established players shunned the other players. He built a ridiculous shrine to Pat Meares, openly taunting management for cutting the injured infielder loose in 2001. (More on Meares in a bit.) Kendall was also among a group of players who mercilessly hazed young shortstop Jack Wilson. Veterans Reggie Sanders and Matt Stairs, who played for the Pirates in 2003, told Kendall he was a bad teammate. (In fairness, note that in 2019, Wilson endorsed Kendall’s bid to become Pirates manager, telling Jason Mackey of the Post-Gazette, “I would say 80-90 percent of [the hazing] wasn’t coming from Jason Kendall. He would put his arm around me and tell me how important I was to the team.”)
There was also the issue of Kendall’s salary, which may have been a factor in the decision to trade Aramis Ramirez in 2003. Finally, Kendall’s performance was declining. He hit .298/.371/.380 from 2001-04 and was worth 10.8 WAR. Hitting at the top of the order, the Pirates would love that type of production today. But his catching skills were eroding and he failed to make the All-Star team during that period, despite playing on bad teams. In November 2004, the Pirates traded Kendall to the Oakland Athletics, unloading one of the worst contracts in their history.
3. There’s No Place Like Home
When Pirates general manager Neal Huntington signed Lonnie Chisenhall to a one-year, $2.75 million contract, it made sense. Chisenhall played for the Cleveland Indians from 2011-18. The left-handed batter hit a solid, if unspectacular, .268/.320/.427, 64 HR, and 296 RBI during that time. As a third baseman and right fielder, it looked like he was a good fit. The Pirates’ regular right fielder, Gregory Polanco (whose five-year, $35 million contract was also one of the worst contracts in Pirates history), was to miss the first half of the 2019 season after shoulder surgery. Chisenhall would play right field in his absence, then slide to third base if young Colin Moran couldn’t cut it and Jung Ho Kang didn’t bounce back after two years off.
There was also risk. Chisenhall was frequently injured in 2017 and 2018, appearing only in a combined 111 games. Sure enough, as a Pirate, Chinsehall was hit by a pitch and injured his wrist in a spring training exhibition game. He began the season on the injured list. Seven games into his rehab assignment at Triple-A Indianapolis, he pulled a calf muscle. It was decided he would rehab the injury at home. He never appeared in a game for the Pirates.
2. Operation Shutdown
After nine major league seasons, journeyman John Vander Wal appeared to have finally found a home in Pittsburgh in 2000. Acquired from the San Diego Padres to fortify the Pirates bench, manager Gene Lamont soon realized Vander Wal was their best option in right field. Vander Wal responded with a career-best .299/.410/.563, 24 HR, and 94 RBI stat line.
However, with the Pirates moving to PNC Park in 2001, new manager “Llegendary” Lloyd McClendon pushed for general manager Cam Bonifay to sign free agent Derek Bell to play right field, citing how Bell would improve team chemistry. (Personally, I’d take the 24 bombs and 94 RBI. You can have the chemistry.) With the New York Mets in 2000, the right-handed-swinging Bell hit .266/.348/.425, 18 HR, and 69 RBI. So, in December 2000, Bonifay signed Bell to a two-year, $9 million contract. The deal was a disaster. In 2001, Bell hit a paltry .173/.287/.288, 5 HR, and 13 RBI in 46 games before a pulled hamstring ended his season.
“I Ain’t Going Out There to Hurt Myself in Spring Training”
Bell came to spring training in 2002 thinking he was guaranteed to be the Pirates’ Opening Day right fielder. When Bell learned he was competing for a job, he spewed this now-famous diatribe, which is certain to one day be the lead paragraph in his obituary, to Dvorchak:
“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.
“Ask [Dave] Littlefield and ask [McClendon] if I’m in competition. 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.”
Oops! The Pirates had a new GM in Littlefield. He had no incentive to give Bell a second chance in the hopes of making Bonifay’s deal look good. Once Bell became aware of the backlash his remarks caused, he backtracked. He said he worded them wrongly and that “Operation Shutdown” was a hip-hop term. (Being tragically unhip as I am, I’m not a hip-hop fan. But when I search “Operation Shutdown” and “hip-hop,” nothing comes up that would exonerate Bell.) Bell was cut in spring training and was out of baseball for good.
1. Damaged Goods
Finally, we come to the curious case of the aforementioned Pat Meares. The extension he signed will go down as one of the worst contracts in baseball history, not just for the Pirates. This is not because of anything Meares did or didn’t do. The culprit in this tale is bad luck.
Beginning his career with the Minnesota Twins from 1993-98, Meares was quietly one of the better shortstops in baseball. Known for his scrappy style of play, the right-handed batter hit .265/.301/.381, 41 HR, and 303 RBI as a Twin. It was said he was a tough out and a good teammate. In September 1998, he turned down the Twins’ offer to extend his contract for three years and $11 million. Instead, Meares tested free agency and sought a four-year, $16 million contract. Unable to find a suitor to meet his demands, the Pirates signed him to a one-year, $1.5 million deal in February 1999.
A Great Mystery
So far, so good. Unfortunately, in a late spring training game, Meares suffered a sprain and pinched cartilage in his left wrist. He was never the same player after that. Despite beginning the 1999 season on what was then called the disabled list and being able to grip a bat with just the top two fingers of his left hand, on April 30, Bonifay signed Meares to a four-year, $15 million extension. He would appear in just 21 games in 1999. In 2001, he was moved to second base and produced a weak .211/.244/.304 stat line in 86 games. That was his final season in baseball.
Again, there was a new GM in Littlefield, and he didn’t feel bound to justify Bonifay’s transactions. Littlefield declared Meares a permanently injured player. Meares received all of his guaranteed $15 million, while the Pirates recovered 70 percent of what they paid him for 2002-03 via an insurance claim. Why Bonifay rewarded Meares after he was injured with a deal he couldn’t get on the open market is one of the Pirates’ great mysteries.
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