Theo Epstein brought in several great players, but he also signed several free agent busts including Carl Crawford.
The Red Sox have signed both valuable free agents and regrettable free agents in the last ten years. Unfortunately for the general managers, their worst additions get more scrutinized that their popular signings.
Last week, B/R posted the “10 Worst Contracts in Boston Red Sox History.” Below is the starting lineup of the worst Red Sox signings over the last 10 years, with a player at every fielding position, a complete starting rotation, two relief pitchers and a manager.
The whole roster is worth more than half a billion dollars and estimated to be around $562 million. Carl Crawford's contract alone makes up $142 million of the estimated $562 million invested in these free-agent busts.
Some of these names will make Red Sox fans cringe, but only one player on the list is still with the team. However, he happens to currently be the team’s highest paid player per year.
Boston GM Ben Cherington plans to utilize the team’s “large payroll” for 2013. Hopefully, no new players will be added to this list in the near future thereby.
J.D. Drew struck out more than 100 times in three of his five seasons with Boston.
For $14 million a year, J.D. Drew is one of the most expensive free-agent busts the Red Sox have ever had (and stuck with). Once a fifth overall pick, Drew never had any remarkable seasons in the National League from 1998 to 2006, yet the Red Sox took an expensive risk with the right fielder.
From 207 to 2011, not once did Drew hit more than 25 homers, more than 70 RBIs or higher than a .280 batting average. He did post good OBPs of .373, .408 and .392 in his first three seasons, but the $14-million-man was a bust.
Drew averaged just 16 HRs and 57.2 RBIs per season with the Red Sox.
The right fielder did hit a clutch grand slam in the Game 6 of the 2007 ALCS—called the “$14 million grand slam”—to help get the Red Sox to the World Series.
Other than that moment, Drew was an expensive $70 million bust for the Red Sox for five seasons.
The three-time Gold Glove Award winner played just 81 games in a season and a half with the Red Sox.
Mike Cameron was at the end of his career when he signed with the Red Sox in 2010. He had already played 15 MLB seasons with six different teams.
Cameron played just 81 games between 2010 and 2011 with the Red Sox. In 2010, he hit .259 with four HRs and 15 RBIs in 48 games, and in 2011, he hit just .149 with three HRs and nine RBIs in 33 games.
Cameron was a three-time Gold Glove Award winner, so Cameron's signing forced Jacoby Ellsbury from center field and to move to left field.
In 2011 when Cameron left the team in a trade with the Marlins, Ellsbury won the Gold Glove Award at the center field position.
For $15.5 million, the Red Sox got just 81 games and 256 at-bats out of Cameron over two seasons.
Carl Crawford stole just 23 bases over 161 games in two seasons with the Red Sox.
The Red Sox signed a monster deal to invest in Carl Crawford for seven expensive years. Turns out, he only played for the team for a disappointing year and a half.
In 2010, Crawford earned an AL All-Star selection, Gold Glove and Silver Slugger Award. In 2011 and 2012, he was persistently scrutinized by Red Sox fans and media for his lack of performance and injury issues.
From 2011 to 2012, Crawford played just 161 games with the Red Sox before being traded to the Dodgers. In 2011, he hit 29 doubles, seven triples, 11 HRs and 56 doubles with just a .255 AVG.
Entering the season, Crawford advertised in Dunkin' Donuts TV commercials as a threat on the base paths, but he stole just 18 bases in 2011. He stole 97 total bases in 2009 and 2010 combined with the Rays, but just 23 bases in 2011 and 2012 combined with the Red Sox.
In 2012, Crawford did not play with the Red Sox until July 16, and he underwent season-ending Tommy John surgery in August. In just 31 games that year, he hit .282 and slugged .479 with 14 extra base hits and 19 RBIs.
The Dodgers will now have to pay the 31-year-old left fielder more than $100 million over the next five seasons.
Edgar Renteria made a career high 30 errors at shortstop in 2005 with Boston.
After losing the 2004 World Series to the Red Sox, Edgar Renteria joined the reigning champions in 2005. He signed a four-year deal, but played just one full season with the team.
In his one season with Boston, Renteria hit .276 with 36 doubles, 70 RBIs and nine stolen bases, and he amassed a career-high 30 errors at shortstop.
This is the same player who won Gold Gloves in 2002 and 2003 with the Cardinals. This is the same player who also hit .330 with 47 doubles, 13 homers, 100 RBIs and 34 stolen bases in 2003.
Renteria was traded to the Braves the following season, and he only made 24 errors in two seasons combined with Atlanta, while hitting .293 and .332 in 2006 and 2007, respectively.
And, in 2010, he earned the World Series MVP as the starting shortstop for the San Francisco Giants.
Nick Punto was just 6-for-49 (.122 AVG) in his first two months with the Red Sox.
Nick Punto was at least a very cheap free agent, but he posted a WAR of -0.2 in 65 games with the Red Sox in 2012.
Last season, Punto hit .200 and slugged .272 with only seven extra base hits, 10 RBIs and 33 Ks in 125 at-bats with the Red Sox. Through April and May, he was just 6-for-49 (.122 AVG) with one double and three RBIs.
On top of that, it was painful to see someone play so badly in the No. 5 jersey, the famous number that legendary Nomar Garciaparra wore. Garciaparra was, and still is, idolized by many in Boston.
Punto played 159.2 innings at third base with the Red Sox in 2012, and he was part of the blockbuster trade that sent Crawford, Gonzo and Josh Beckett to the Dodgers.
In 22 games with Los Angeles, the utility infielder hit better with a .286 batting average, but he recorded only one extra base hit and no RBIs.
I'm sure that very few, if any, Red Sox fans still value their Julio Lugo signed memorabilia.
Though Julio Lugo mostly played shortstop with the Red Sox, he did play one game in left field with the Sox and 30 games at second base for the Cardinals in 2009. So I think Lugo could handle the second base position in this fantasy starting lineup of recent Red Sox free-agent busts.
Lugo had several decent years with the Tampa Bay (Devil) Rays, but in his final months with the Dodgers in the 2006 season, he hit just .219 and slugged .267 over 49 games.
Despite his .237 AVG, Lugo had a decent 2007 season with the Red Sox, posting 36 doubles, 73 RBIs and 33 stolen bases. However, he had 19 errors in that first season with Boston.
Lugo played just 119 games in 2008 and 2009 with the Red Sox, accumulating 23 errors and only 20 extra base hits over that span.
The shortstop was traded after just two and a half seasons with the Red Sox. The team still had to pay the final year and a half of his contract while he played for the Cardinals and Orioles.
Tony Clark hit just three home runs with the Red Sox in 2002.
Tony Clark replaced Brian Daubach as the Red Sox everyday first baseman in 2002. The former Tiger crushed 97 homers and 321 RBIs from 1997 to 1999, but he was mediocre in 2000 and 2001, hitting just 29 homers and 112 RBIs.
Despite Clark's statistical fall off, the Red Sox still signed the first basemen.
In 2002, his lone season with the Red Sox, Clark hit a mere .207 and slugged a terrible .291 with three HRs and 29 RBIs in 90 games.
Clark was useless against left-handed pitchers that season, batting .159 and slugging .256 against southpaws.
After losing Mo Vaughn after 1998, for several years the Red Sox could not find a solid starter at first base.
Until they landed Kevin Millar.
There really haven’t been any high-paid, disappointing catchers for the Red Sox in the last 10 years.
The only player who could be nominated is Kevin Cash, who hit just .111 (3-for-27) with one double, four RBIs and 13 strikeouts, while striking out almost every other at-bat in 2007. However, he was signed to a cheap, minor league deal, and Tim Wakefield had one of his better seasons pitching with Cash catching for him in 2008.
Given the lack of overpaid, underperforming catchers acquired by the Red Sox from free agency in the last 10 years, one catcher's major blunder makes the list instead of a player.
Kelly Shoppach’s awful slide and stolen base from 2012 earned him the catcher’s position on the lineup of recent Red Sox free-agent busts.
Shoppach signed with the Red Sox for the second time in his career in December 2011. Entering April 13, 2012, he had never attempted a stolen base. But Shoppach got his first career MLB steal that day in hilarious fashion.
You can watch the video above.
Dice-K was rocked in his final Red Sox start and the final four seasons of his career with Boston.
Don't forget to factor in the $51.1 million posting fee to negotiate with him.
Daisuke Matsuzaka was scouted to have a lethal “gyroball” and stuff like a No. 1 pitcher. He certainly didn’t pitch like a No. 1 pitcher in his tenure with the Red Sox, but he’s the No. 1 pitching free agent signing bust of the last 10 years for the Red Sox.
Dice-K did show some flashes of dominance during his six years with the Red Sox. His first season was below average, posting a 15-12 record with a 4.40 ERA, 201 strikeouts and 25 homers allowed, but he did earn a win in Game 3 of the World Series against the Rockies.
In his second season, Dice-K pitched like an All-Star and showed off his “No. 1 stuff,” posting an impressive 18-3 record with a 2.90 ERA.
Then, everything fell apart.
In his final four seasons, Matsuzaka posted a 17-22 record with a 5.53 ERA. Last year, in his final season with the Red Sox, Dice-K posted a 1-7 record with an 8.28 ERA. In his final start, he allowed six hits, five runs, two homers and one walk over just 2.1 innings in Yankee Stadium on October 3.
Dice-K gave the Red Sox one great season with several scattered great starts. But in the end, his scouted “gyroball” was a meatball crushed by opposing batters.
The Red Sox will never get back that $103 million they paid for Dice-K.
The Red Sox have a 30-31 record in games John Lackey pitched for them between 2010 and 2011.
John Lackey has earned just under $50 million in three years with the Red Sox, and he’s earned just 26 total wins as the team’s starter since 2010.
In 2010, Lackey had a below average season, posting a 14-11 record with a 4.40 ERA, his highest ERA since 2004. In 2011, Lackey had a terrible season, posting a 12-12 record with a career-high 6.41 ERA, a career-high 1.62 WHIP and 20 homers allowed over just 28 starts.
In 2012, the Red Sox paid John Lackey
to not lose games to undergo Tommy John surgery and sit out the whole season.
The Red Sox will pay Lackey more than $30 million for another two seasons. Unless Cherington makes a big, expensive free agent splash, Lackey will enter the 2013 season as the team's highest-paid player.
The 34-year-old can pitch his way off this list, but for now, he’s considered one of the biggest free agent busts—possibly the biggest—in the last 10 years for the Red Sox.
Matt Clement posted a 6.61 ERA and 1.76 WHIP in his final season with the Red Sox.
Matt Clement was one of the more overrated players the Red Sox signed in the last 10 years. Entering 2005, he had a career 69-74 record, and only twice did he have an ERA below 4.00 at a season's end.
Clement did make the 2005 AL All-Star team, posting a 10-2 record, 3.85 ERA and 1.26 WHIP in his first 18 starts, but after the All-Star game, he pitched nothing like an All-Star.
In his final 14 starts of the season, Clement posted a 3-4 record with a 5.72 ERA and 1.51 WHIP. In his lone postseason start, he allowed seven hits, eight runs and three homers over just 3.1 innings in the ALDS loss.
In 2006, Clement had a 5-5 record with a 6.61 ERA and 1.76 WHIP over 12 starts, and he was released the following year.
Julian Tavarez posted a 4.94 over his three seasons with the Red Sox as a starter and a reliever.
Before signing with the Red Sox, Julian Tavarez rectified his career as a relief pitcher with the St. Louis Cardinals. He posted a career-best 2.38 ERA in his final year with the team in 2005, which fooled the Red Sox into signing him as a starter and reliever.
Tavarez’s ERA climbed in each of his three years with the Red Sox. He posted a 4.47 ERA, 5.15 ERA and 6.39, respectively, from 2006 to 2008 with Boston.
Tavarez posted a 4.94 ERA and allowed 135 earned runs over 246 innings in the three seasons combined with Boston.
In 2007, he received his first and only World Series ring. This was the same year Manny Ramirez pet Tavarez's head in the dugout, which is a must-see YouTube video that even got the broadcasters chuckling.
John Smoltz had a great career but posted terrible numbers in his lone year with Boston.
The Red Sox hoped that John Smoltz would be a steal for just a one year deal in 2009. After a great 2007 season, Smoltz started just five games in 2008, while posting a 2.57 ERA, 1.18 WHIP and .229 BAA with 36 strikeouts over 28.0 innings.
In 2009, he was a disaster with the Red Sox.
In eight starts, Smoltz posted a 2-5 record with an 8.33 ERA, 1.70 WHIP and .343 BAA. In his lone start versus the Yankees, the long-time Brave allowed nine hits, eight runs, two homers and four walks over just 3.1 innings.
After the start in Yankee Stadium, Smoltz was traded to the Cardinals, where he finished his career. He posted a 4.26 ERA and 1.18 WHIP in seven starts with the Cardinals.
Ramiro Mendoza pitched well with the Yankees but terribly with the Red Sox.
After winning four World Series titles with the Yankees in 1996, 1998, 1999 and 2000, Ramiro Mendoza switched sides in the rivalry and signed with the Red Sox for two years.
Mendoza began his career as a starter and eventually evolved into a reliever. In his final two seasons as a full-time reliever with the Yankees, he posted a 3.75 ERA in 2001 and a 3.44 ERA in 2002.
In 2003, he signed with the Red Sox and had the worst season of his career, posting a 6.75 ERA, 1.77 WHIP and a .349 BAA. His stats were even worse at Fenway Park that season, posting a 0-3 record with a 10.66 ERA, 2.13 WHIP and .404 BAA.
Despite throwing just 30.2 innings in 2004 and earning the losing decision in the 19-8 loss to the Yankees in Game 3 of the ALCS, Mendoza still won his fifth career World Series with the Red Sox that season.
Bobby Jenks didn't convert one save with the Red Sox.
Bobby Jenks finally gets his opportunity to be the Red Sox closer. When signing with the team, some Red Sox fans believed he would replace Jonathan Papelbon as the team’s closer. Jenks recorded 167 saves over five years with the White Sox prior to signing with the Red Sox.
Jenks didn’t convert one save in his only year with the Red Sox.
The flamethrower tossed four hitless innings in his first four appearances with the Sox. But in his next relief appearance, Jenks allowed four hits and four runs over just 0.1 innings and never recovered.
Jenks finished 2011 with 19 appearances, a 6.32 ERA, 2.23 WHIP and .328 BAA. He allowed 22 hits, 11 earned runs and 13 walks over just 15.2 innings.
Jenks has not pitched with the Red Sox (or anyone else) since July 7, 2011. He never got the opportunity to be Boston’s closer.
Bobby Valentine was fired after just one season managing the Red Sox.
One season. 69 wins. 93 losses.
The day after the 2012 Red Sox season ended, Bobby Valentine was fired as the team’s manager.
Bobby V was regularly booed by the Fenway Faithful, openly criticized by his own players and was the center of criticism for the team’s dreadful season.
Valentine was replaced by John Farrell as the Red Sox manager, but he earned a spot in the starting lineup as the manager of the Red Sox worst free-agent signings in the last ten years.
With $70-80 million in spending money this offseason, hopefully Cherington will not sign anyone who will be added to this lineup of recent Red Sox free-agent busts.