Justin Masterson and Other Former Boston Red Sox They Wished They Kept

Patrick LanguzziContributor IIIAugust 5, 2011

Justin Masterson and Other Former Boston Red Sox They Wished They Kept

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    Justin Masterson came back to Fenway Thursday evening to beat his former teammates for the third time in four starts since being traded to the Cleveland Indians in 2009 along with Bryan Price and Nick Hagadone for catcher and first baseman Victor Martinez.

    Masterson was drafted by the Boston Red Sox in the second round of the 2006 amateur draft.

    Masterson who is 9-7 with a 2.63 ERA threw six innings allowing three runs and striking out nine while outperforming Eric Bedard in his Red Sox debut.

    Boy wouldn't Masterson look good right about now in the third spot of that Sox rotation?

    "He's good, and we see his best," said Red Sox manager Terry Francona. "I'm sure he enjoys pitching against us. He's really good. The things he needed to work on when he was a young pitcher -- getting in to lefties -- he can do that now. He's not timid throwing it in, and he can elevate when he wants to. He's impressive." 

    It seems like it's been tradition for the Red Sox going back for decades in letting some good players go. In the following slides you'll see my top five picks of players over the years the Red Sox let go for one reason or another that ended up going on to do great things!

5. Hanley Ramirez

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    Hanley Ramirez was signed by the Boston Red Sox as an amateur free agent in July of 2000. 

    He was traded to the Florida Marlins in November of 2005 along with Harvey Garcia, Anibal Sanchez, and Jesus Delgado for Josh Beckett, Mike Lowell, and Guillermo Mota.

    Although some might say the deal worked out well, considering what the Red Sox got in return with Beckett and Lowell, Ramirez is now a three-time All-Star and went on to win the 2006 National League Rookie of the Year Award, two silver sluggers, and a batting crown.

    Considering how many shortstops the Red Sox have had over the last few years, they may want this one back!

4. Jeff Bagwell

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    Jeff Bagwell was drafted by the Boston Red Sox in the fourth round of the 1989 amateur draft. He was traded to the Houston Astros for Larry Andersen and a bag of balls.

    In 1991 he took home National League rookie-of-the-year honors. He won the 1994 National League Most Valuable Player Award and finished six times in the top 10 in MVP voting.

    He rounded out his 15-year career with 449 HR and received 41.7 percent of the votes his first year on the Hall of Fame ballot, 2011.

    That's one I'm sure they would love back!

3. Sparky Lyle

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    Sparky Lyle was drafted by the Red Sox from the Baltimore Orioles in the 1964 first-year draft. 

    After five years with the Red Sox, Lyle was traded in November of 1978 to our beloved New York Yankees for Danny Cater and a player to be named later.

    Lyle went on with the Yankees to win the 1977 Cy Young Award, make three All-Star appearances, and win a World Series.

    He finished his World Series career as a Yankee with a 1.93 ERA.  

2. Curt Schilling

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    Curt Schilling was drafted by the Boston Red Sox in the second round of the 1986 amateur draft.

    He was traded along with Brady Anderson at the July trade deadline in 1988 to the Baltimore Orioles for Mike Boddicker.

    This deal actually wasn't too bad because Boddicker worked out fairly well with the Red Sox for three seasons, helping the Sox finish first in two of those years.

    I'm going to give the Red Sox a pass on this one since they ended up redeeming themselves when they re-aquired Schilling in November of 2003 in a trade with the Arizona Diamondbacks for Michael Goss, Casey Fossum, Brandon Lyon, and Jorge de la Rosa.

    Schilling was already a five-time All-Star and World Series co-MVP before returning to Boston.

    We all know what happened after that. They won the first of two World Series with Schilling in 2004, their first in 86 years!

1. Babe Ruth

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    George Herman "The Babe" Ruth.

    Where do I begin?

    He is probably the most famous and arguably greatest player ever to live, and the Red Sox decided to let him go to our beloved New York Yankees for some cash and theater tickets.

    Ruth was purchased by the Red Sox from Baltimore for more than $25,000.

    He led almost every offensive category and was an extremely effective lefty pitcher while playing in Boston for six years before being sold off to the Yankees in January of 1920. In fact, in 1916 he led the league with a 1.75 ERA, 40 games started, and nine shut outs.

    Probably one of the most lop-sided deals ever conducted in baseball.