The 15 Biggest Boston Red Sox Busts in History

Daisuke-Matsuzaka

One of the most prestigious franchises in sports history, the Boston Red Sox have a storied past that includes greats like Babe Ruth, Ted Williams and Pedro Martinez. Unfortunately, like all sports teams, not everyone who has donned the Boston ‘B’ on their hat has turned out as great, though. Whether they were drafted, signed for as a free agent or acquired through trade, here are the 15 biggest busts in Boston Red Sox history.

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15. Jose Malave

Signed as a free agent in 1989 out of Venezuela, outfielder Jose Malave lasted just 45 games with the big-league club before getting sent back down to the minors and bouncing around between a few others leagues. With just four homers and 17 RBI, batting a measly .226, Malave definitely wasn’t the solution in the outfield for Boston.

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14. Adrian Gonzalez

With a monster, seven-year, $154 million deal, Adrian Gonzalez was supposed to be the centerpiece of the next generation of Red Sox stars. Having a great first season in Boston, Gonzalez’s tenure in Boston ended midway through his second year, getting traded in a blockbuster deal to the L.A. Dodgers as the Red Sox didn’t think a $22 million a year salary was warranted for what he was providing.

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13. Jose Offerman

After failing to sign big bopper Mo Vaughn to a big deal and watching him leave in free-agency, the Red Sox turned to Jose Offerman to replace him. Inking a four-year, $26 million deal, Offerman hit just .268 and bashed 30 homers, failing to ever come near the numbers that Vaughn gave the Red Sox in his time with the club.

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12. Julio Lugo

Almost never being a full-time starter prior to Boston giving him a four-year deal worth $36 million, shortstop Julio Lugo was looked at as a fine complementary player in a loaded lineup back in 2007. Hitting just .251 in two-plus seasons with the team, Lugo was so bad that the team actually designated him for assignment rather than try and stick it out with him.

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11. Matt Young

Signed as a free-agent for three years and $6.5 million, Matt Young was expected to help bolster a Red Sox rotation in 1991 that was led by Roger Clemens. Things didn’t go as planned, though. Managing to make just 16 starts his first season, he posted a 5.18 ERA and only started eight more games the rest of the time in Boston.

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10. Craig Hansen

Drafted in the first-round in 2005, when the Red Sox got pitcher Craig Hansen—an All-American closer from St. John’s—they handed him a four-year, $44 million deal thinking he would become a star. With just two saves in 74 appearances and an ERA at 6.15, Hansen didn’t live up to the deal or high selection.

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9. Brian Rose

A local star who was from nearby New Bedford, Brian Rose was thought to be the next great pitching prospect for the Sox. Winning the International League’s MVP for a pitcher in 1997, Rose got a starting nod in 1998, making just eight starts and finishing with an 11-15 record and 5.73 ERA in his Boston career.

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Daisuke-Matsuzaka-red-sox

8. Daisuke Matsuzaka

Daisuke Matsuzaka was supposed to come over from Japan and set MLB on fire with his wicked pitches and funky windup. And while he had a good first season in which he won 15 games and a sophomore year with 18 wins, the rest of his time in Boston was dreadful, as he posted a record of 17-22 and failed to find and command on his pitches. It was tough to swallow considering the team paid over $100 million to acquire him.

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Edgar-Renteria

7. Edgar Renteria

A former World Series hero for the Florida Marlins, Edgar Renteria got a four-year, $40 million deal following the 2004 World Series win for the BoSox in hopes of helping bring another title to Fenway. He struggled big time, though. Instead of playing his, normally solid, defense, Renteria committed 30 errors and lasted just one season with Boston before getting dealt in 2005.

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6. Wilton Veras

Playing just 85 games in his Sox career, third-baseman Wilton Veras was a free swinger who the Boston faithful thought would bring some pop to the team’s lineup. Signed as a free agent in 1995, Veras had a little success in his rookie year but struggled mightily in his follow-up campaign, ending his MLB career.

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5. J.D. Drew

One of the biggest disappointments of any former No. 1 overall pick, J.D. Drew’s tenure in Boston was anything but spectacular. Signing a five-year, $70 million deal, Drew wasn’t a bad player, but he never lived up to the hype that came with him when he was first drafted. And in Boston, for a guy who was getting paid $14.5 million per season, he was simply just one of the guys and a frequent punching bag for Sox fans who expected more.

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frankie-rodriguez

4. Frankie Rodriguez

A former Junior College MVP, the Boston Red Sox drafted Frankie Rodriguez in the second-round of the 1990 MLB draft and handed him a monster signing bonus, hoping he would fit well either at shortstop or on the mound. Focusing on pitching, Rodriguez had little control, being traded in 1995 following an 0-2 record and 10.57 ERA in nine games with Boston.

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3. Steve Avery

Having success in the mid-’90s with the Atlanta Braves in a stacked rotation, lefty pitcher Steve Avery was brought to Boston through free-agency in 1997, with the team giving him the highest-paid pitcher in their rotation. He couldn’t justify the deal, though, winning just 16 games in two years with an ERA of 5.61.

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2. John Lackey

While with the Anaheim/Los Angeles Angels, John Lackey was exactly the type of pitcher that the Red Sox adored. He was tough, blue-collared and pitched with an edge. That’s why the team gave him a five-year, $82.5 million deal, but he couldn’t deliver on his performances, with Boston fans never seeing the guy who excelled with the Angels for all of those years, going just 47-43 with a 4.46 ERA in his four seasons.

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1. Carl Crawford

One of the worst signings in Boston Red Sox history, when Carl Crawford joined the team in 2011 by getting a seven-year, $142 million deal, Crawford struggled with injuries and consistency in his one-plus year with the team before being traded away. Batting just .260 and stealing only 23 bases in that time, it’s safe to say that Fenway’s faithful never saw the All-Star that he showed he was before coming to Beantown.

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Written by Nick Dimengo

Graduate of the University of Kentucky. Cleveland sports fan. Frustrated respecter of LeBron James. Influencer of bad ideas. In addition to Worthly/Housely, I'm a regular contributor to Bleacher Report, Scout, Esquire and Maxim, and run or bike way too much for my own good when not writing. The day a Cleveland sports team wins a title is the day I can officially say my life is complete.