Boston Red Sox: Best free agent signings in franchise history
The Red Sox have deep pockets and have never been afraid to spend money on free agents. Here’s a look at the best ones they’ve signed in their history.
One of the luxuries of playing in a baseball-crazed area of the country is that the Boston Red Sox have money…lots of money. They also have been more than willing to spend it over the years (although that seems to have changed for the time being). While there have been multiple instances of the team investing big contracts in players who ended up being busts, they’ve also hit on just as many.
The following is a list of the best free agent signings the Red Sox have made since free agency came to Major League Baseball in 1976. Some of these players ended up spending the bulk of their careers in Boston, others were only here for a short time before moving on again, but all were instrumental in helping the Red Sox win.
In fact, on this list there is only one free agent who didn’t win a World Series with the Red Sox before moving on although in his case, he’s almost certain to be enshrined in the Hall of Fame which is a pretty good consolation prize.
In no particular order, let’s begin.
Manny Ramirez
The signing of Manny Ramirez is not only one of the best in Red Sox history, it also might be the most important. He was the first marquee free agent to sign in Boston and not only opened the flood gates for other big names to consider the Red Sox in free agency, but along with Pedro Martinez and David Ortiz, energized the city’s Dominican population into a loyal segment of the fanbase.
Ramirez spent the first eight seasons of his career in Cleveland before becoming a free agent in the winter of 2000. Then-Red Sox GM Dan Duquette signed him to a ten-year, $200 million contract that was the second largest of all time behind only Alex Rodriguez (who signed his record-breaking ten-year, $250 million deal that same winter).
Manny immediately paid dividends, hitting .306 with 41 home runs and 125 RBI in his first season in Boston in 2001. In the World Series winning years of 2004 and 2007, Ramirez hit .308 with 43 home runs and 130 RBI and .296 with 20 home runs and 88 RBI, respectively. He was also named World Series MVP in 2004.
For his Red Sox career which ran from 2001 to 2008, Manny put up a .312 average to go with 274 home runs and 868 RBI. From 2003 to 2008 he teamed up with David Ortiz to form one of the most potent 3-4 tandems in all of baseball. As for his defense, Ramirez wasn’t the greatest left fielder, but that wasn’t why the Red Sox signed him in the first place.
With his goofy personality and carefree approach to the game, not to mention his gorgeous swing, Manny became a fan favorite despite his defensive shortcomings and frequent lack of hustle. “Manny being Manny” was tolerated and celebrated until it began to wear thin in 2008.
His Red Sox career came to an ugly end and he was traded at the 2008 deadline, but for eight years Manny thrilled Boston fans with his relentless hitting. Even better, he showed other top free agents that Boston was a place worth going to in free agency.
Johnny Damon
The visual embodiment of 2004’s Idiots, if not their spiritual leader, Johnny Damon was one of the best free agents the Red Sox ever signed when they inked him to a four-year, $31 million deal in the winter of 2001. Damon became the Red Sox leadoff hitter and center fielder and one of the best in the league at both during his Boston years.
In his four seasons with the Red Sox, Damon hit .295 with 56 home runs, 299 RBI, 98 stolen bases, a .362 OBP, and 461 runs scored. His finest season came during the historic 2004 campaign when he hit .304 with 20 home runs, 94 RBI, a .380 OBP, and 123 runs scored.
He hit a torrid .467 in the 2004 ALDS and while he struggled in the ALCS, he will forever be remembered for his two monster hits in the clinching game seven at Yankee Stadium. He hit a grand slam and a three-run homer to help the Red Sox complete their historic comeback and win the pennant. He carried that into the World Series where he hit .286 with a home run and two RBI.
With his long hair and beard, Damon was nicknamed “the Caveman” and became a fan favorite. During the 2005 season as he approached free agency he stated in an interview that “there’s no way I can go play for the Yankees, but I know they’re going to come after me hard. It’s definitely not the most important thing to go out there for the top dollar, which the Yankees are going to offer me. It’s not what I need.”
However, at the end of the season he spurned the Red Sox three-year contract offer to take the Yankees offer which was for four years and $52 million. Almost immediately he went from fan favorite to villain, but time has healed those wounds and there’s no question that Damon was an essential component of the 2004 team and thus a great signing.
David Ortiz
This is the big one and has to go down as the greatest free agent deal the Red Sox ever made. David Ortiz is quite simply the single-most important player in Red Sox history. In addition to his countless clutch hits during his fourteen seasons in Boston, he was the face, heart, and soul of the Red Sox.
In the winter of 2002, Ortiz was released by the Minnesota Twins and became a free agent. At the urging of Pedro Martinez, then-GM Theo Epstein signed Ortiz to a non-guaranteed $1.25 million deal which only went into effect if he made the team coming out of spring training. He did and as we all know, the rest is history.
While originally signed to help give the Red Sox some depth at first base, Ortiz ended up being the team’s DH for the rest of his career and what a hitter he was. He hit .288 with 31 home runs and 101 RBI in his first year with the club and was a big reason they got all the way to game seven of the 2003 ALCS before losing in heartbreaking fashion.
His 2004 season was even better as he hit .301 with 41 home runs and 139 RBI. Through 2008 he’d combine with Manny Ramirez to make one of the most potent hitting tandems in all of baseball. With those two guys coming in the three and four spots of the order, opposing pitchers had no way to pitch around either of them and the two Sox sluggers made them pay.
Ortiz cemented his place as a Boston sports legend with his numerous clutch and game-winning hits during the 2004 postseason, most notably his series-winning home run in game three of the ALDS against the Angels and his two game-winners in games four and five of the ALCS.
Ortiz was one of the main reasons the Red Sox finally ended their drought in 2004 and had he never played another game for the team, he’d already have been a Boston sports god. Instead he helped the team win two more World Series in 2007 and 2013 while mentoring each new generation of homegrown Red Sox stars.
From Kevin Youkilis to Dustin Pedroia to Mookie Betts and everyone in between, Ortiz was the one constant for the Red Sox from 2003 to 2016. For his Red Sox career, he hit .291 with 483 home runs and 1530 RBI. He set the franchise single-season record for home runs with 54 in 2006 and retired in 2016 at the age of 41 after hitting .315 with 38 home runs and 127 RBI in that final season.
“Big Papi” was a larger than life personality who always had a smile on his face but played with an intensity that was fearsome. He was synonymous with the Red Sox for fourteen years and was there to comfort fans and steel their resolve in the face of tragedy in 2013 when he declared that “this is our ****ing city!” before the first game played after the Boston Marathon bombings.
While he spent most of his career as a DH, Ortiz looks to be a lock for Cooperstown when he’s eligible in 2022 thanks to his exploits at the plate with the Red Sox. Without Ortiz, the Red Sox don’t win the World Series in 2004 and from there, who knows how history might have unfolded? Instead, they’re the winningest franchise (in terms of championships) in all of baseball this century.
For all of that and then more, David Ortiz is the greatest free agent signing the Red Sox have ever made.
JD Drew
JD Drew got a bad rap from baseball fans, Red Sox and otherwise. There were a couple of things that people pointed to, but usually it boiled down to the fact that it seemed as though he just didn’t care. In reality, that was a misconception as Drew was so skilled and had such a laid back personality that he gave off that impression even though it almost certainly wasn’t true.
He also did have a reputation for being a bit fragile, but when the Red Sox signed him to a five-year, $70 million contract in January 2007, there was excitement at what he could bring to the right field position. He had a bit of a down season that first year, hitting .270 with only 11 home runs and 64 RBI, but he came through when they needed him in the postseason.
Facing elimination in game six of the ALCS, Drew hit a grand slam that helped the Red Sox win the game and eventually the pennant. In that series he hit .360 with a home run (the grand slam) and six RBI. He then hit .333 in the World Series as the Red Sox won their second title of the century.
Drew’s next three seasons were better as he hit 19, 24, and 22 home runs. He had more big hits in the 2008 postseason, hitting the game-winner in game two of the ALDS. In game five of the ALCS with the Red Sox facing elimination he hit a two-run home run to help them come back from a seven-run deficit. He then had the walk-off hit in the ninth inning which won the game for Boston.
After playing in 137 and 139 games in 2009 and 2010, respectively, Drew was plagued by injuries in his final season of 2010 and only appeared in 81 games. He retired after the season, ending his fourteen-year career.
JD Drew wasn’t a flashy player at all, but he was calm and steady and very good. He was an excellent defensive outfielder and delivered numerous clutch hits in big situations. Overlooked during his career, it can be said with hindsight that his signing was actually a very good one for the Red Sox, certainly better than what they got out of his brother a few years later.
Adrian Beltre
This one is more of a “what might have been” for the Red Sox, although what they got was pretty damn good in its own right. Adrian Beltre had been an excellent third baseman for the Los Angeles Dodgers and Seattle Mariners before becoming a free agent after the 2009 season. Coming off the worst season of his career, the Red Sox signed him to a one year deal worth $9 million with a player option for $5 million for 2011.
The deal was widely seen as one which would allow Beltre to either rehabilitate his career or kill it off for good. For the Red Sox, there was minimal risk since it was only for a year, but they lucked out when Beltre bounced back in a big way. In his lone season in Boston, he led the team with a .321 average and hit 28 home runs and 102 RBI. He also led the major leagues with 49 doubles.
While he did lead all third baseman with 19 errors, there was no doubt that fans and team alike wanted Beltre back in 2011. However, he instead took an offer from the Texas Rangers with whom he’d play the final eight seasons of his career, picking up his 3000th career hit along the way.
He was only in Boston for a year, but Adrian Beltre was a great signing and one of those players most Red Sox fans wish had stuck around longer so we could have seen what might have been.
David Price
“Wait a minute, didn’t you put David Price on your list of the Red Sox worst free agent signings?” I can hear you asking this, so let me head you off right now and answer by saying that yes, I did and as (perhaps) a cop-out, I think he belongs on both lists.
In the previous list, I went through the reasons why I considered Price one of the worst free agents the Red Sox signed. The gist of it was that while he wasn’t bad, he wasn’t great and given the investment they put in him (seven years and $217 million), the Red Sox didn’t get their money’s worth.
Price had two really good seasons and two injury-plagued seasons in Boston. Those were all reasons I factored in then, so how can I turn around now and say he was also one of their best free agent signings? For many of the same reasons (I told you this was a cop-out).
As stated in that last article, he was really good during the 2016 and 2018 regular seasons and his pitching in the 2018 ALCS and World Series were huge reasons why they won both of those series. I’m not going to post his numbers again (you can find them in the other list), but I will say this one more time: he should have won World Series MVP over Steve Pearce.
The real reason David Price is on both lists is because I could make a compelling case for both. Also, while he wasn’t much liked by fans and the media, his teammates all seemed to love him and that probably accounts for something, I guess. Anyway, let’s move on to the last one.
JD Martinez
After being released by the Houston Astros in 2013, JD Martinez remade his swing and became one of the premier hitters in all of baseball. After stops in Detroit and Arizona, the Red Sox signed him to a five-year, $110 million contract in February 2018 to fill the void left by David Ortiz retiring after the 2016 season.
The 2017 Red Sox struggled to replace Ortiz’ production and had a down offensive year as a team. Martinez slid seamlessly into the cleanup spot in the order and helped power the Boston offense to their greatest season in franchise history. Martinez flirted with the Triple Crown all season and finished the year hitting .330 with 43 home runs, 130 RBI, 111 runs scored, a .402 OBP, and an OPS of 1.031.
That postseason he hit .357 in the ALDS, .278 in the ALCS, and .278 in the World Series with a combined three home runs and 14 RBI as the Red Sox won their fourth World Series of the century. He followed it up with a slightly down season in 2019, but only when compared to his own lofty standards; it was a season anyone else would have been thrilled with.
Martinez hit .304 with 36 home runs, 105 RBI, 98 runs scored, a .383 OBP, and an OPS of .939 in 2019. With the possibility of Martinez opting out after the season (he has an opt-out for each of the final three years on the deal), there was a real fear that the Red Sox would lose his bat, especially since he was on a relatively cheap deal.
Next. Top home run hitters in Red Sox history. dark
Instead, he opted to stay and will be on the Red Sox for the 2020 season (whenever that may start). Martinez has carried the torch from Ortiz in providing monster production in the heart of the order and combined with the money the Red Sox are paying him, is one of their best free agent signings ever.