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LEEinks List: Biggest names to leave Boston via free agency

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Although the season is not yet over for the Red Sox, speculation already has begun about whether or not the team will resign All-Star third baseman Adrian Beltre. Because Beltre undoubtedly will warrant top dollar, there is a good chance the Sox may pass on locking him up long-term. Good players come and go through a city all the time; it is the nature of the game. A player performs well during a contract year, or finishes up a long deal with the team, and decides a change of scenery is necessary.

With that in mind, we thought it would be a good idea to put together a list of the best players who have played here and then decided to leave for greener pastures via free agency.

10. Jason Bay

Bay came to the Red Sox in the Manny Ramirez deal in 2008, showing fans right away why he was an All-Star outfielder for the lowly Pirates. In his two years in Boston, he batted .274 with 45 home runs and 156 RBI. He seemed to be a perfect fit on the team. Instead, he joined the Mets in the offseason, and has struggled in New York, battling both injury and inconsistent play.

9. Luis Tiant

Tiant made his MLB debut with the Indians in 1964, and in 1968 led the league in ERA (1.60) and shutouts (9). The Cuban right-hander then came to Boston in 1971 and became one of the more popular players in the team’s history. Unfortunately for Sox fans, Tiant joined the Yankees at the end of the ’78 season, playing two years with the Bronx Bombers.

8. Mo Vaughn

The “Hit Dog” had many memorable seasons with the Red Sox and did great charity work for the city of Boston. The three-time All-Star, however, did not get along with the team’s brass, often butting heads with then general manager Dan Duquette. After the ’98 season, Vaughn singed a monstrous six-year, $80 million deal with the Angels, which at the time was the largest contract in the game. His career went downhill from there.

7. Johnny Damon

One of the “idiots” of the 2003 Red Sox, Damon came from Oakland and quickly made an impact with the team and the fan base. In four years with the Sox he hit .295 with 98 stolen bases and 29 triples. He was also an integral member of the 2004 team that won the organization’s first World Series in 86 years. Like Tiant, he left to wear pinstripes in New York. He was heartily booed upon his return to Fenway.

6. Curtis Martin

Drafted in 1995, Martin won Offensive Rookie of the Year honors after helping lead the Patriots to their second Super Bowl appearance in January 1997. Then, after the following season, Martin decided to join former Pats coach Bill Parcells in New York, signing a six-year, $36 million contract to play for the Jets. The five-time Pro Bowl running back finished his career with 14,101 rushing yards, which is good for fourth all-time in NFL history.

5. Asante Samuel

A fourth-round pick of the Patriots in 2003, Samuel emerged as one of the best cover corners in the league during his tenure in New England. He won two Super Bowls with the team in 2003 and 2004, but after the Patriots’ loss to the Giants in Super Bowl XLII, left to sign with the Eagles. The Patriots did not make any significant moves to sign the cornerback, and he accepted a six-year, $56 million deal with Philadelphia. In his five years in New England, he recorded 211 tackles to go along with 22 interceptions and three touchdowns.

4. Pedro Martinez

Martinez came to the Red Sox in November 1997 via a trade with the Expos, and he signed a record six-year, $75 million deal (at that time, the largest ever awarded to a pitcher). He put together two Cy Young seasons in 1999 and 2000, and will go down as one of the best pitchers in the history of the game. His outgoing personality fit in well with the city of Boston, and when he left after the team’s World Series championship in 2004, many fans were devastated.

3. Carlton Fisk

Pudge came up through the Red Sox system, making himself into one of the best catchers in the game. His first full season was 1972, and he had stayed with the team until 1980, when he joined the White Sox. Because of a mix-up by Red Sox GM Haywood Sullivan (he sent a formal offer in the mail a day late), Fisk became a free agent and signed a $3.5 million deal with Chicago. He played the rest of his Hall of Fame career on the South Side, calling it quits in 1993.

2. Roger Clemens

The Rocket spent the first 12 years of his career with the Sox, winning three of his six Cy Young awards in Boston. Clemens won 192 games with the team, which is tied with Cy Young for the franchise record. Sox GM Dan Duquette infamously let Clemens go after the 1996 season, claiming he was in the twilight of his career after four seasons of mediocrity. As most people can recall, that assessment proved inaccurate, and Clemens won 162 more games with the Blue Jays, Yankees and Astros.

1. Bobby Orr

The man who made the sport of hockey popular in the city of Boston had a somewhat unceremonious departure from the Bruins. After spending 10 successful seasons with the Bruins and winning two Stanley Cups, Orr finished up the last two years of his illustrious but injury-filled career with another Original Six team, the Blackhawks. Orr’s agent at the time, Alan Eagleson, reportedly withheld information regarding the Bruins’ contract offer (which was said to one of the most expensive in sports history, on top of 18 percent team ownership), and steered him to Chicago. Orr will forever be known for his exploits at Boston Garden, but his final two years away from the team ‘€” during which time he played in a total of just 26 games due to his bad knees ‘€” cannot go unnoticed.


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