Ten Worst Boston Red Sox Free Agent Signings of All Time

While drafting players and developing them through the farm system is the ideal solution, every team must dip into the free agent pool from time to time. As Red Sox Nation has learned, not for the first time, these signing don’t always work out. Scott Maxwell brings us the ten worst Boston Red Sox free agent signings.

The recent news that Pablo Sandoval has been lost for the 2016 season brings the topic of the worst free agent deals in Red Sox history to the forefront. Though they have had plenty of success in the free agent market, the failures have been every bit as fantastic. For the sake of discussion, this list does not include amateur or international free agents. Daisuke Matsuzaka and Rusney Castillo, you’re off the hook… for now.

10. Jack Clark, 1991

The Red Sox signed the slugger to a 2-year, $5.8M contract, making him the highest-paid position player on the team before the 1991 season. Over the course of two seasons in Boston, Clark slashed a mere .236/.366/.412. His 1992 season was dreadful (.210/.350/.311 over 81 games), leading Clark to hang up his cleats after his 18th season.  

9. Julio Lugo, 2007

If not for turning in a fantastic performance in the 2007 World Series, Lugo would likely find himself further up the list. He signed a 4-year, $36M deal prior to the 2007 season. Lugo had played successfully in the division with the Devil Rays and had displayed an ability to get on base and steal some bases. 2007 was the only season during which he was able to stay on the field, but he sported an abysmal .236/.294/.349 slash line. His 2008 season saw him commit 16 errors by the All-Star break, forcing the team to call up rookie Jed Lowrie to share playing time. The final tally in Boston: 3 seasons, 266 games, .319 OBP. If only he had warned a former teammate not to come to Boston a few years later…

8. John Smoltz, 2009

A number of free agents on this list had success at previous stops. None had more than Hall of Famer John Smoltz. One of the best pitchers of his era, Smoltz was coming off shoulder surgery entering his age 42 season. The Red Sox signed him to a 1-year deal worth a total of $10M with incentives. Smoltz posted just a 2-5 record with an 8.33 ERA in only eight starts before being released. It turned out to also be the final year of his career. No doubt, during his Hall of Fame induction speech, many Red Sox fans shook their collective heads remembering some of those eight brutal starts. He’s not the only former Brave to disappoint on this list.

7. Matt Young, 1991

1991 was not a good year for free agent signings. Young had mild success prior to arriving in Boston, which made his contract and performance stand out. He earned roughly the same amount as eventual Cy Young winner Roger Clemens in 1991. Over the course of two seasons, Young amassed a 3-11 record with a 4.91 ERA. The only highlight of his career was losing a game in which he had not allowed a hit through 8 innings. Since he never pitched the ninth inning, he did not receive credit for a no-hitter. The Hall of Fame even rejected the ball that he sent. Makes you almost feel bad for him. Almost.

6. Matt Clement, 2005

The Red Sox were coming off their first World Series win in nearly a century and had just said goodbye to the legendary Pedro Martinez and Derek Lowe. Enter Clement. He got off to a great start and earned an All-Star selection in 2005. It all fell apart after that, when Clement was struck in the head by a line drive off the bat of Carl Crawford on July 26, 2005, and was never the same. The right-hander had a 5.09 ERA over two seasons and got shelled for 8 runs over 3.1 IP in his only postseason start. He had season-ending shoulder surgery in 2006 and never made an appearance in the 2007 championship season. In fact, Clement would never take the mound again in the major leagues. Fenway, where pitching careers go to die.

5. Steve Avery, 1997

The 1990’s Atlanta Braves were a pitching goldmine. Along with the aforementioned Smoltz, Avery was part of the Braves team that went to the World Series in consecutive seasons 1995-1996. The Red Sox banked on Avery making the adjustment to the American League, signing the lefty to a 2-year, $8.75M deal. Avery would get rocked in the AL East to the tune of a 5.64 ERA and won just 16 games over his two seasons. The Red Sox search for a legitimate #2 starter behind Pedro Martinez would continue for several more seasons.

4. Jose Offerman, 1999

After the departure of beloved star Mo Vaughn, Dan Duquette famously said that Offerman was brought in to replace Vaughn’s on-base capabilities. No pressure, Jose. Though Offerman was selected to play in the legendary 1999 All-Star Game for the home team, he never lived up to his 4-year, $26M deal. His fielding declined dramatically, and the team had enough concerns about his defense at second base that they moved him over to first after just one season.. Oh, and that OBP? .365 over three seasons, well below Vaughn’s .402 in his final season in Boston. Jose would eventually be banned from baseball in the Dominican Republic for punching an umpire and hitting two players with a bat. Quality guy.

3. Edgar Renteria, 2005

Renteria’s experience in Boston should have served as a cautionary tale for other members of this list. He was successful with the Cardinals and was offered a comparable contract to stay in St. Louis. He opted to take a few more dollars and sign a 4-year, $40M deal with Boston. He replaced fan-favorite Orlando Cabrera after the magical 2004 season and never seemed comfortable in his new home. Renteria set a career high with 30 errors in 2005 and lasted only one season before being dealt to Atlanta.

2. Pablo Sandoval, 2015

Fear not, Panda, you may soon top the list. Still, Pablo has done yeoman’s work to climb this list so quickly. Sandoval was signed to a ridiculous 5-year, $95M deal, creating expectations that he never had a chance to meet. The Giants’ postseason star was wanted back by his old club, with some protections such as a weight clause. Seems like they knew a little more about doing business than former-GM Ben Cherington, who presumably lost his job over this and other disastrous moves. In 2015, Sandoval was rated the worst position player in the major leagues with a -2 fWAR. As was already mentioned, Sandoval is likely out for the season after playing just 6 belt-breaking games. He showed up for spring training grossly overweight and lost his starting job to Travis Shaw. Things do not look good for the future of this contract, and he seems more likely to move up this list than to drop down. Still, he has some work to do yet before he can match the next signing, which was also the undoing of another Red Sox GM.

1. Carl Crawford, 2011

Oh, the horror. Theo Epstein was once the toast of the town in Boston, and may be soon in Wrigleyville. However, the end of his Red Sox tenure was punctuated by the ill-advised 7-year, $142M deal to Crawford. If Renteria looked uncomfortable in Boston, the Carl Crawford experience was excruciating. After years of torturing the Red Sox with his bat and on the basepaths, Epstein decided he was worth the gigantic deal. Crawford was offered a similar deal by the Los Angeles Angels, where he likely would have been more comfortable. Despite his contention that he was treated unfairly in Boston, fans gave him tremendous leeway despite his pitiful performances. His batting average in his first year dropped 52 points from the previous year in Tampa. He swiped just 18 bags after stealing 107 bases in his previous two seasons combined. It was a nightmarish fit that has repercussions to this day. The 2011 club scuffled down the stretch, surrounded in controversy. Two legends, Epstein and Terry Francona, left the organization. The following season, the Red Sox had to package All-Star Adrian Gonzalez, fan favorite Nick Punto and the mercurial Josh Beckett to Los Angeles Dodgers just to unload Crawford’s albatross of a contract. The Red Sox had given up a guy named Anthony Rizzo to obtain Gonzalez, and both players have had tremendous success after leaving the Red Sox organization. The far-reaching effects of this horrible deal make it an easy choice as the worst in team history.

Dishonorable Mention: Tony Clark, John LackeyJustin Masterson, Andre Dawson, David Wells, A.J. Pierzynski

Scott Maxwell has written about the best free agent signings from each teams in the American League and the National League.

Follow Scott on Twitter @marbleheader75.

About Scott Maxwell 5 Articles
Scott is a teacher, husband and father living in New Hampshire. His hobbies include travel, collecting baseball cards, playing wiffle ball, and digging in to the history of baseball. He has been a moderator and member of SoSH.net for over a decade and has led discussions with John Henry, Ben Cherington and Mike Hazen.

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