Will Carl Crawford Pan Out? Grading the 10 Biggest Contracts in Red Sox History

The Boston Red Sox made some major moves this off-season, but none bigger than the decision to sign Carl Crawford to a 7-year, $142-million contract.

The contract made Crawford the second highest paid outfielder in team history. Nobody knows for sure whether Crawford will live up to his lucrative deal for the Sox, but for the time being it sure looks like a smart move.

After all Crawford has tormented the Red Sox has a hitter, fielder, and baserunner for the last decade as a member of A.L. East rival Tampa Bay Rays.

If he can stay anywhere near the numbers he has been producing in recent years, and help lead Boston to a World Series Championship, then he will be worth every penny of the deal.

Here is a look at the ten biggest contracts in recent history and how the expensive decisions turned out for the Red Sox front office.

10. Daisuke Matsuzaka, 2006

Grade: D+

The Red Sox out bid several teams for the right to negotiate with Matsuzaka with price of $51 million as posting fee. He then agreed to a six-year, $52 million contract with options for future years.

Stories of dominance in Japan and of a pitch known as the gyroball created much buzz about Matsuzaka going to Boston. In retrospect it is hard to argue any of that buzz was justified.

Daisuke has posted a 4.18 ERA and his earned run average was 4.40 or higher in all but one season. On top of that Matsuzaka has been at constant odds with the Red Sox staff regarding injuries.

The only thing keeping this from a failing grade is the fact that he pitched well for one season and has pitched surprisingly well in the playoffs.

In 2008 Matsuzaka reached high point in his career when he went 18-3 with a 2.90 ERA. However he has always struggled with control, and even in that season he posted a 1.32 WHIP.

If the Red Sox office could go back they would assuredly rescind the $103 million spent on Matsuzaka.

9. John Lackey, 2009

Grade: C-

Lackey signed a five-year, $82.5 million contract with the Red Sox, but struggled with inconsistency in his first season.

Lackey was completely average in 2010 when he posted a 14-11 record with a 4.40 ERA. However, the Red Sox are definitely not paying him average money.

All signs point to better years in the future. Lackey has the demeanor a pitcher needs to survive in Boston so it is possible he was just in an adjustment year.

However, he will have to pitch far better if he ever wants to justify the contract he received from the Sox.

8. J.D. Drew, 2007

Grade: C

In 2007 Drew signed a five-year, $70 million contract to become a member of the Boston Red Sox.

From then on he has had many peaks and valleys in Boston. He is remembered for his grand slam in game six of the ALCS versus the Cleveland Indians in 2007.

Drew also actually appeared in his first ever All-Star game as a member of the Red Sox.

However, his demeanor has never seemed to fit in Boston. His lack of visible emotion has caused many to believe that he does not really care.

He also is not the type of player to play through injuries and his status for games was constantly up in the air, which did not exactly endear him to Red Sox Nation.

7. Josh Beckett, 2006

Grade: B

The first extension that Beckett got from the Sox was a four-year, $40 million deal with incentives. If his grade was based solely on this then he would have received a much higher grade.

After all Beckett was the ace of the staff that led the Red Sox to the 2007 World Series Championship. He also was the ALCS MVP and has been a two time All-Star in Boston.

However, Beckett also signed a four-year, $68 million deal through 2014 which may not be as successful. Since signing the contract Beckett had an injury riddled season and posted a career worst 5.78 ERA.

If Beckett can not get back to form then this will be a contact that hangs over the Red Sox for the next four seasons.

The upcoming 2011 season will go a long way in determining Beckett's health and whether he can the be type of pitcher he was during his early run in Boston.

6. Adrian Gonzalez, 2011

Grade: B+

Admittedly this is cheating because Gonzalez is yet to actually sing an extension. However this is solely due to a business decision that delays some of the payment the Red Sox have to make.

In the end it appears inevitable that Gonzalez will sign something along the lines of a seven-year, $172 million deal to become a member of Red Sox Nation.

Obviously it is tough to give Gonzalez a grade, as he is yet to actually produce any kind of numbers in a Red Sox uniform.

However, his swing and demeanor seem to fit the bill perfectly in Boston. If he can provide the big bat in the middle of the order with numbers similar to his days in San Diego, then he will be worth the contract.

If Gonzalez adds a World Series Championship (or two) on top of that then his grade could go even higher.

5. Nomar Garciaparra, 2007

Grade: B+

Some may be surprised to see the grade this low for the beloved shortstop. After all he was a six time all-star and the face of the franchise for many years in Boston.

Garciaparra also won back to back batting titles and was a constant threat for the MVP.

However, he also struggled with injuries throughout much of his career. He basically missed the entire 2001 season due to a wrist injury, and had several other DL stints during his years in Boston.

Garciaparra also declined defensively over his time in Boston. Eventually it came to the point where him and the Red Sox were no longer in a working relationship and he had to be traded.

Garciaparra's grade is also lower because he was never part of the team the brought the World Series back to Boston.

4. Dustin Pedroia, 2008

Grade: B+

Pedroia signed on with the Red Sox with a six-year, $40.5 million dollar deal. Since then he has certainly lived up to the contract.

While in Boston Pedroia has won an MVP award, a Gold Glove award, and has been to three All-Star games.

He also was the number two hitter for the 207 Red Sox championship team. His hard style and tendency to speak his mind has made Pedroia a fan favorite in Boston.

If he can rebound from an injury-filled 2010 season then Pedroia should find himself rising on this list.

3. David Ortiz, 2006

Grade: A-

After a monstrous 2007 season Ortiz signed a deal that ended up being for five years and worth $62.5 million.

Based on production and legacy Ortiz grade should probably be even higher. After all he was the driving force behind the Red Sox 2004 World Series Championship.

During the postseason in 2004 Ortiz .370 with three home runs and ten runs batted in, including two walk off hits against the Yankees in the ALCS.

During his days in Boston Ortiz has also been a six time All-Star, finished in the top five of MVP voting five times, and led the American League in home runs for a season.

Most importantly he has earned a reputation one of the most feared hitters in the league when the game is on the line.

One thing that slightly holds down Ortiz's grade is his drop in batting average over the past several seasons. However, the major factor that reduces his grade is a report that in 2003 he tested positive for a banned substance.

2. Manny Ramirez, 2000

Grade: A-

In 2000 the Red Sox signed Ramirez to an eight-year, $160 million deal with options for two additional season.

The only reason this grade is not perfect is because of Ramirez's volatile behavior. His trade demands throughout his years in Boston are well documented. Ramirez also has several altercations, sometimes physical, with players, coaches, and staff members.

While with the Red Sox Ramirez won a batting title, led the league in home runs, and was on nine straight All-Star teams.

More importantly he helped the Red Sox break an eighty-six-year curse as the World Series MVP. As if that were not enough he was a part of the 2007 World Series Championship team as well.

1. Pedro Martinez, 1997

Grade: A

In 1997 general manager Dan Duquette traded for Pedro Martinez and quickly signed him to a six-year, $75 million contract.

Over that time he arguably became one of the greatest, if not the greatest, pitcher in the long history of the franchise. Over that time Martinez won two Cy Young awards, and was selected to six All-Star teams.

In 1999 Martinez had one of the greatest pitching seasons of all time when he led the American League in wins, earned run average, and strikeouts. The following season he tried to one up himself and finished the year with a minuscule 1.74 ERA.

Statistically Martinez was almost definitely the best pitcher in baseball during his years with the Red Sox. In fact he had an ERA under three for six out of his seven season in Beantown.

As if all of that was not enough, Martinez was also an intricate part of the 2004 Red Sox team that broke the eighty-six-year curse.