Worst Free Agent Contracts in Pittsburgh Pirates History

The Pittsburgh Pirates traditionally do not spend a whole lot of money in Free Agency. This also suggests that the team traditionally does not sign many players of prominence.

Unfortunately for the Pittsburgh Pirates and their fans, many of the free agents that the Organization has brought in have not really worked out. That tends to happen when you play pretend and do not actually invest in the team but rather just trying to fill holes with aging veterans or busted prospects. Obviously though, through the years the team has made some deals bad or good.

However, that has been the curse that has hung over the Pittsburgh Pirates for the better part of the last 30 years. The reality is these moves have traditionally not worked out for the Pittsburgh Pirates. Even during their few competitive years, from 2012-2016, the team struggled to bring in outside talent.

The Pittsburgh Pirates deserved to be criticized for the way their team operates especially in free agency. Up until this year, the Bucs were hardly even handing out Major League contracts let alone aggressively pursuing upgrades. Maybe it is because they have been burned in the past, spending resources and not getting any positive results from the deal. Why spend now if you are not going to win? Still, every team in Baseball needs to be successful in some capacity in Free Agency. The Pittsburgh Pirates have not had this success, let's take a look at their 15 signings that wound up being failures.

#15 Francisco Liriano, 3-year $39 million

Francisco Liriano was a pitcher who played for the Pittsburgh Pirates from 2013 to 2016. Liriano was acquired by the Pirates in a mid-season trade with the Minnesota Twins in 2012 and quickly became one of the team's most reliable starting pitchers. His initial contract with the Pittsburgh Pirates worked out, it was a 2-year deal. In 2013 he owned a 3.02 ERA while in 2014 he earned a 3.38 ERA.

After two strong years and two playoff appearances, the Bucs decided to bring Liriano back during the 2014-2015 offseason. The Bucs handed him out one of their biggest free agents contracts ever by giving the lefty a 3 year $39 million deal. In 2015 he would go on to once again own an impressive ERA at 3.38. However, that would be it.

The year that this free-agent contract became bad was in 2016. Liriano owned one of the worse ERAs in all of Baseball in 2016, 5.46 in just over 100 innings pitched. This is why this contract ended up being one of the worst in Franchise History.

At the trade deadline, the Pittsburgh Pirates offloaded Liriano to the Toronto Blue Jays. This trade was not well received by any means. First and foremost the Bucs only received one player back in the deal, in Drew Hutchinson. At this point, Hutchinson was considered a bust and there were really no expectations for him upon joining the Organization. Going the other way with Liriano were former first-round pick Reese McGuire and one of the team's top 20 prospects in outfielder Harold Ramirez.

Both McGuire and Ramirez have carved out Big League careers in their own right. Hutchinson never panned out with the Pittsburgh Pirates, being released by the Organization in 2017. Meanwhile, the Bucs gave up two solid prospects and paid bascially half of the extension Liriano was given. Not a good deal, but they did receive a successful 2015 from him, making it somewhat more favorable than the others.

#13 Joe Randa, 1-year $4 million

Before the 2006 season, the Pittsburgh Pirates struck a deal with veteran third baseman Joe Randa. Randa was brought in on a 1-year deal for his age-36 season. This deal made really no sense for the Pirates at the time. The expectations were relatively low at this point, with general manager Dave Littlefield having one foot out the door.

Randa played in 89 games and had 324 at-bats in the 2006 season. He recorded 81 hits, including 16 doubles, 1 triple, and 8 home runs. He had a batting average of .251, an on-base percentage of .299, and a slugging percentage of .392. Randa drove in 42 runs and scored 33 runs himself. walked 20 times and struck out 39 times. Defensively, Randa made 8 errors in 84 games at third base, finishing with a .955 fielding percentage.

Overall, Randa's 2006 season was decent, but not one of his best. He provided some power with his eight home runs and was a reliable defender at third base, but his batting average and on-base percentage were below his career averages. The team also paid him a nice chunk of change at $4 million and was not able to trade him for anything at the Deadline. Overall, a pretty pointless signing and use of money. While those two things are true, Randa was not a terrible pickup, just meaningless.

#12 Matt Diaz, 2-year $4.25 million.

Matt Diaz was a professional baseball player who spent the 2011 season playing for the Pittsburgh Pirates. Diaz was primarily an outfielder and designated hitter, and he joined the Pirates as a free agent after spending the previous five seasons with the Atlanta Braves.

Diaz had a solid year with the Pirates in 2011, batting .259 with 2 home runs, 13 doubles, and 19 RBIs in 98 games. He also showed good plate discipline, drawing 21 walks while striking out just 27 times.

While Diaz's offensive numbers weren't eye-popping, he was a valuable contributor to the Pirates' lineup. He was especially effective against left-handed pitching, batting .315 against southpaws during the season.

Defensively, Diaz played primarily in left field for the Pirates, but he also saw some time in right field and as the designated hitter in American League games. He had a decent arm and made some solid defensive plays throughout the year. Throw in the fact that he hit lefties extremely well and Diaz was able to be moved at the Trade Deadline.

After signing Diaz to a two-year deal worth just over $4 million, the Bucs traded him before the end of the first year of that contract. Diaz was sent packing to the Braves for a player to be named later, which ended up being Elicier Cardenas who never amounted to anything. Again, a free agent contract was handed out to a player that the team had no real long-term plan to keep. The Bucs paid all of his 2011 salary, and basically had nothing to show for it.

#11 Lyle Overbay, 1 year deal worth $5 million

It was another notable name that the Pittsburgh Pirates brought in to play first base. The team historically has struggled to find a productive first baseman, especially in more recent times. Lyle Overbay was a proven player at this point, so many thought he would be a good addition to the team plus a tradable asset.

During the 2011 season with the Pirates, Overbay played in 121 games and had 432 plate appearances. He had a batting average of .234, an on-base percentage of .310, and a slugging percentage of .438. He hit 35 doubles, 1 triple, and 18 home runs while driving in 59 runs and scoring 52 runs himself. Defensively, Overbay played primarily at first base for the Pirates, where he had a fielding percentage of .996 and committed only four errors in 1,076 total chances.

Overall, Overbay's 2011 season with the Pittsburgh Pirates was one of the worst seasons of his career. Many expected him to provide solid contributions both offensively and defensively to a Pirates team. Instead, the team released him outright in August of that year, paying him his complete contract. If not for Garret Jones breaking out, Overbay would have likely finished the year with the Bucs. The Pittsburgh Pirates finished with a record of 72-90, good for fourth place in the National League Central division. Lyle Overbay would take on the nickname of Lyle "Overpaid" during his final stretch with the Pirates. A nickname well warranted after a disaster of a season.

#10 Jeromy Burnitz, 1 year $6.7 million

The acquisition of Jeromy Burnitz was supposed to be a big-time signing for the Pittsburgh Pirates. The team was bringing in a veteran power hitter after a year when he hit .258 with 24 homers with the Cubs. But again, his season with the Pirates would end up being the last season in the career of Jeromy Burnitz.

Jeromy Burnitz was an outfielder who played for the Pittsburgh Pirates during the 2006 Major League Baseball season. Burnitz was signed by the Pirates as a free agent prior to the 2006 season and was brought in to provide power to the middle of the Pirates' lineup.

Burnitz had a solid start to his time with the Pirates, hitting six home runs in his first 19 games with the team. However, his production quickly tailed off, and he finished the season with a .230 batting average, 16 home runs, and 49 runs batted in.

Despite his struggles, Burnitz did provide some veteran leadership to a young Pirates team that was in the midst of a rebuilding process. He also played solid defense in right field, recording a .988 fielding percentage and committing just two errors in 118 games.

After the 2006 season, Burnitz became a free agent and was not re-signed by the Pirates. He retired from baseball in 2007, finishing his career with a .253 batting average, 315 home runs, and 981 runs batted in over 14 seasons in the major leagues.

#9, Ramon Vasquez, 2 years $4 million

It is almost comical to see how many of these players never played in the Major Leagues after their time with the Pittsburgh Pirates. Ramon Vasquez is in the same boat. The Bucs brought him in during the 2009 offseason, and he did not hit nearly as well as they had hoped.

Ramon Vazquez played for the Texas Rangers during the 2008 Major League Baseball season. He was mainly used as a bench piece He was primarily used as a backup infielder, playing second base, third base, and shortstop as needed.

In 2008, Vazquez appeared in 104 games for the Rangers, hitting .290 with four home runs and 40 runs batted in. He also had a solid on-base percentage of .365 and a slugging percentage of .430. Vazquez played solid defense at all three positions he was asked to play, committing just five errors in 167 total chances.

So it seemed like a really solid pickup when the Bucs gave him a contract. Ramon Vazquez played for the Pittsburgh Pirates during the 2009 Major League Baseball season as a utility infielder. He appeared in 91 games, hitting .230 with three home runs and 27 runs batted in.

Vazquez played solid defense at second base, third base, and shortstop, committing just six errors in 313 total chances. While he didn't put up as strong offensive numbers as he did in 2008, Vazquez still provided depth and a veteran presence to the young Pirates team. All in all, it was a waste of another free-agent contract. The Bucs would be on the hook for the 2nd year of his deal as well.

#8, Eric Hinkse, 1-year $1.5 million

When the Pittsburgh Pirates signed Eric Hinske there was some intrigue but not super high expectations. Hinkse was brought in primarily to be a corner bench bat. What made him an interesting fit for the Pittsburgh Pirates was his power from the left side of the plate.

Over the course of his Big League career, Hinske averaged 16 home runs per 162 games played. A pretty solid number for a player who only played over 140 games in a season 3 times in 12 years. So the thought was bringing his power to PNC Park would be an absolute perfect match. Well, it of course did not work out that way for the Pittsburgh Pirates.

Eric Hinske played in 54 games for the Pittsburgh Pirates in the 2009 season before being traded to the New York Yankees. During his time with the Pirates, he batted .255 with 1 home run, 11 RBIs, and a .710 OPS. He primarily played as a left fielder and first baseman for the team. All numbers that were suggesting a year that Hinske would set multiple career lows.

Luckily for Hinkse, he had an opportunity to prove himself elsewhere. Eric Hinske was traded from the Pittsburgh Pirates to the New York Yankees in June 2009. He played in 39 games for the Yankees during the remainder of the 2009 season, primarily as a left fielder and designated hitter.

Hinske was a valuable contributor to the Yankees' championship run, batting .226 with 7 home runs and 14 RBIs in 84 plate appearances. He hit a key home run in the American League Championship Series against the Los Angeles Angels, helping the Yankees reach the World Series. How typical for the Pittsburgh Pirates, a proven veteran not producing and then leaving to only reclaim his form for another team. Hinkse is just another name in a long list that made 7 figures from the Pirates to essentially not produce.

#7 Tony Armas Jr, 1 year $3.5 million

The Pittsburgh Pirates pitching staff was rather bleak during the Dave Littlefield era. Littlefield could not draft a pitcher if he had to. He passed on the likes of Clayton Kershaw and Zach Greinke in drafts. He also missed by taking pitchers like Brad Lincoln and Daniel Moskos with top selections and them not working out at all.

So when the Pittsburgh Pirates brought in veteran pitcher Tony Armas Jr there was some hope that he would be an upgrade to the team's rotation. In 2007, the Bucs signed him to a 1-year deal with a club option for 2008, which like many of the others on this list would be declined. Armas Jr was a complete bust for the Pittsburgh Pirates.

Armas Jr. signed a one-year, $3.5 million contract with the Pirates on February 1, 2007, with a mutual option for 2008. He was expected to bolster the Pirates' starting rotation, but he struggled from the beginning of the season. In his first three starts, he went 0-3 with an ERA of 8.92.

As a result of his struggles, Armas Jr. was removed from the rotation in late April 2007 and moved to the bullpen. He made six relief appearances before being placed on the disabled list in early May with a strained right forearm. Armas Jr. returned to the Pirates in June 2007 but continued to struggle in both the rotation and bullpen. He finished the season with a record of 4-5 and an ERA of 6.03 in 31 games (15 starts).

The Pirates declined their club option on Armas Jr. for the 2008 season. This essentially ended his career with the Pittsburgh Pirates making him a free agent. He eventually signed with the Boston Red Sox for the 2008 season, where he made six appearances (two starts) before being released in July. Another veteran pitcher brought in who was paid a chunk of money to not produce or be a trade piece.

#6, Erik Bedard, 1-year $4.5 million

Erik Bedard signed a one-year, $4.5 million contract with the Pittsburgh Pirates in December 2011. The contract included performance bonuses based on the number of innings Bedard pitched during the season. He was expected to provide a veteran presence in the Pirates' starting rotation and help the team compete in the National League Central division. Despite battling injuries and inconsistency during his time with the Pirates, Bedard's contract was seen as a reasonable investment by the team at the time.

Erik Bedard played for the Pittsburgh Pirates during the 2012 season. He signed a one-year contract with the team and was expected to bolster their starting rotation. Bedard had a strong start to the season, posting a 2.48 ERA in his first five starts. However, he struggled with consistency and battled injuries throughout the season.

He finished the season with a record of 7-14 and an ERA of 5.01 in 24 starts. The Pirates declined their option on Bedard for the 2013 season, making him a free agent. Overall, his time with the Pirates was marked by a mix of promising performances and struggles with consistency and injuries. The hope was that Pittsburgh Pirates would be able to trade Bedard at the deadline for a return. That was disappointing at the time, but not surprising given the year he had.

#5 Rod Barajas, 1 year $4 million

In November 2011, Rod Barajas signed a one-year contract with the Pittsburgh Pirates worth $4 million. The signing was seen as a move by the Pirates to address their need for a veteran catcher who could help mentor their young pitching staff. Barajas was coming off a productive season with the Los Angeles Dodgers in which he hit .230 with 16 home runs and 47 RBIs. Although he struggled offensively during his time with the Pirates, Barajas was praised for his work with the pitching staff and his ability to handle a young and inexperienced rotation.

Rod Barajas played as the starting catcher for the 2012 baseball season. He started the season with the Pittsburgh Pirates on a one-year deal with a club option for year 2. During his time with the Pirates, Barajas struggled at the plate, hitting just .206 with 11 home runs and 31 RBIs in 78 games. However, he was known for his solid defense and game-calling abilities behind the plate.

Overall, Barajas had a well below-average season offensively but was valuable to both the Pirates for his defensive skills, game calling, and mentorship to the pitchers. Barajas was mainly brought in for those reasons along with the team needing a catcher. The Bucs would not exercise their option to bring him back for 2013.

Another reason was that newly acquired pitcher AJ Burnett had worked with Barajas in the past and they had a very good relationship. If not for those reasons Barajas probably would not have even made it to August with the team. At the time a young Michael "The Fort" McKenry was showing promise as a potential backup catcher.

#4 Pat Meares, 1-year $1.5 million

Pat Meares began his Major League Baseball career with the Minnesota Twins in 1993, where he played for six seasons as a reliable infielder. Meares had a solid career with the Twins, playing in 742 games and batting .258 with 52 home runs and 275 RBIs.

After becoming a free agent in 1998, Meares signed with the Pittsburgh Pirates for the 1999 season. In his first year with the Pirates, Meares played in 21 games before suffering a season-ending injury. He bounced back in 2000, playing in 152 games and batting .273 with 14 home runs and 71 RBIs. The following year, Meares played in 66 games and batted .255 before being released by the Pirates in August 2001.

Throughout his career, Meares was known for his solid defensive skills at shortstop and third base. He was also a consistent hitter, finishing his career with a .266 batting average, 68 home runs, and 346 RBIs. He did not carry this success to Pittsburgh. In 1999 with the Pirates, he batted a career-high .308 but in just 21 games. The Bucs would give him a 4-year $15 million extension before his injury that season, again money that should not have been handed out.

In 239 games with the Pirates, Meares batted .238 with 196 hits, including 37 doubles, 3 triples, and 17 home runs. He scored 97 runs and drove in 79, with 55 walks and 156 strikeouts. He stole one base and was caught twice. His on-base percentage was .294, and he slugged .352, giving him an overall OPS (on-base plus slugging percentage) of .647.

After his release from the Pirates, Meares played briefly in the minor leagues before retiring from baseball in 2003. He played a total of 981 professional baseball games over his career, with 742 of those games played with the Minnesota Twins and 239 games played with the Pittsburgh Pirates. Meares played his final Major League Baseball game on October 7, 2001, against the Chicago Cubs.

#3 Raul Mondesi, 1-year $1.75 million

Raul Mondesi was a right fielder for the Pittsburgh Pirates. He signed a one-year pact with the club, which included an option for year 2. Of course, like many others, he would not have that 2nd year with the Pittsburgh Pirates. He had been performing well for the team with a batting average of .283, two home runs, and 14 runs batted in before he abruptly left the team on May 7th, 2021.

Mondesi left the team to return to his native Dominican Republic to fight a lawsuit that was filed against him. The details of the lawsuit were not made clear in the report. However, it is evident that his prolonged absence from the team led to a breach of contract.

The Pirates management became increasingly frustrated with Mondesi's absence and lack of communication with the team. According to the team's spokesperson, Mondesi did not respond to their attempts to contact him, and his whereabouts were unknown.

As a result, the Pittsburgh Pirates decided to terminate their contract with Mondesi due to the breach of contract. The team cited the breach of contract as the reason for ending all dealings with Mondesi, effectively releasing him from the team.

#2, Lonnie Chisenhall, 1-year $2.75

Lonnie Chisenhall was a free-agent outfielder brought in from Cleveland. He signed a one-year, $2.75 million contract with the Pittsburgh Pirates, as announced by the team on November 26, 2018. The signing was made to provide an experienced, productive, and versatile player to the team. Also, he would be considered a potential option in right field while Gregory Polanco recovered from an injury.

Chisenhall's contract also included incentives, which could amount to a potential $3 million boost if he reached certain plate appearance milestones. However, given his past performance and the likelihood of him receiving platoon duty, it was unlikely that Chisenhall would maximize his contract. No one expected what would occur.

Chisenhall would break his hand/finger in Spring Training of 2019. He would miss a couple of months due to it before getting back to game action. However, the game action was at Triple-A Indianapolis, not the Big League Club. Chisenhall would quickly land back on the injury list, with his hamstring nagging him once more. The possibility of outfielder Lonnie Chisenhall playing for the Pirates that season was dismissed by the team. Chisenhall remained at home in Bradenton, Fla., mending from left calf troubles, and there wasn't enough time for him to return to the majors that year.

This would be the end for Chisenhall with the Pittsburgh Pirates. He would leave the team and rehab at home with his family. This of course led to him retiring at the end of the year. Not a single game played for the Pittsburgh Pirates and earned almost $3 million for the year. A wasted investment and one that fans were actually optimistic about.

#1 Derek Bell, 2-years $10 million

Derek Bell's last season in Major League Baseball was in 2001 with the Pittsburgh Pirates, and it was a season plagued with controversy and poor performance. Bell, who was 32 years old at the time, struggled both on and off the field, and his statistics for the season were some of the worst of his career.

In 2001, Bell played in 46 games for the Pirates, accumulating 183 plate appearances and 156 at-bats. He hit .173 with three home runs, five doubles, and 13 RBIs. He had a slugging percentage of .288 and an on-base percentage of .287, with a total of 38 strikeouts and 25 walks. These numbers were a significant decline from his career averages.

Off the field, Bell was involved in controversy when he refused to participate in a spring training game, citing knee pain. Pirates manager Lloyd McClendon criticized Bell for not being willing to play through pain, and Bell responded by saying that he was "contemplating retirement" and that he didn't "need the money."

Coming into year 2 of his contact, Bell was told he would be competing for a spot on the roster. Bell, who was a career .276 hitter while playing in over 1200 career games, did not feel a competition was warrented. However, in the Pittsburgh Pirates eyes they had a 33 year old who was greatly declining physically and in performance. In what would become known as "Operation Shutdown" Bell would leave the team without notifiying anyone at the end of March 2002. He would be released days later with a violation of his contract being the reasoning.

Bell ultimately did retire after the 2001 season, and his poor performance and controversy that year were seen as contributing factors to his decision. However, he left behind a solid career in Major League Baseball, having played for five teams over 12 seasons and amassing 1,261 hits, 123 home runs, and 592 RBIs. He was also a member of two World Series championship teams, with the Toronto Blue Jays in 1992 and the New York Yankees in 1999.

After being released by the Pirates in March 2001, Derek Bell never played professional baseball again. Meanwhile, he still got the $4.5 million he was owed under his contract. Upon leaving the Organization, Bell moved on to a 58-foot Sea Ray 580 yacht, which he named Bell 14 after his name and uniform number.

Bell was known to spend a lot of time on his yacht, enjoying the lifestyle that his baseball career had afforded him. He also stayed involved in baseball, working as a scout for the San Francisco Giants and later as a consultant for the Houston Astros. One of the worst contracts in Franchise history, Bell not only did not perform in the first year of it, but he also made a complete embarrassment out of himself and the Organization.