Boston Red Sox all-time best free agent signings

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The BoSox Injection staff takes a look back at the all-time best free agent signings in Boston Red Sox history.

Mandatory Credit: Peter G. Aiken-USA TODAY Sports

Free agency is a gamble fraught with significant risk and just like at the casino, the house usually wins. When elite talent hits the free agent market they expect to be paid based on past performance, despite that every win they helped secure during their last contract unfortunately doesn’t carry over to the new one.

In an ideal world teams would offer contracts based on what those players are projected to be worth for the duration of the contract, but that rarely works in an environment where teams with deep pockets are forced to bid against each other for the services of a limited number of premium talent. The laws of supply and demand often work in the player’s favor, which is why we see so many long-term deals extend well beyond a player’s prime.

The Boston Red Sox find themselves in such a predicament after finalizing a lucrative deal with free agent pitcher David Price. Their desperation to acquire an ace to anchor their rotation led the Red Sox to spend $217 million on a 30-year old pitcher, which is a significant u-turn from the philosophy ownership held as recently as a year ago. As one of the best pitchers in the game over the last several years, Price will be worth every cent of his contract for as long as he remains in his prime, but the expectation is that the Red Sox will need to keep paying him like an ace even after he hits his decline years. Will Price produce enough on the front end of his deal to have been worth it by the end? It’s too soon to tell.

Such is the gamble of free agency. It may not end well, but that doesn’t mean that the price they pay won’t be worth it in the end. The Red Sox don’t have the best track record when it comes to signing expensive free agents, particularly in their recent history, but it hasn’t been all bad.

Let’s look back at the ten best free agent signings in Red Sox history to prove that despite the risks of paying market prices, free agency isn’t always a losing bet.

Next: Keith Foulke

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Keith Foulke

Keith Foulke was a successful closer when the Red Sox signed him to a three year, $18.5 million contract on January 7, 2004. After the Red Sox had come agonizingly close to the 2003 World Series, the team was in need of an established reliever to finish the 9th inning. Manager Grady Little did not go to his bullpen when he should have, despite their great performance in that American League Championship series, allowing a 5-2 eighth inning lead to slip out of the team’s grasp in Game Seven, perhaps due to the lack of a shutdown closer.

Foulke led the American League in saves (43) and games finished (67) in 2003 for the Oakland A’s, whom the Red Sox had beaten in the Division Series that year. The Red Sox got an elite closer for 2004 who was unusual in that he could get more than three outs, pitching at least 77 innings each of the prior five seasons. In 2004, the Red Sox used him 19 times for more than three outs. When they needed him the most, down 3-0 to the Yankees in the 2004 ALCS, he proved his durability. In Game 4, he threw 50 pitches over 2.2 innings in the Red Sox 6-4, 12 inning victory. He had thrown over 30 pitches only one time that season. Over the next two days, Foulke threw an additional 50 pitches, totaling 100 pitches in three days. He allowed one hit and no runs over five innings in that span. He saved Game Six in New York in dramatic fashion to keep the Red Sox hopes alive.

After Foulke carried the Red Sox to their 2004 title, he was not the same pitcher, perhaps feeling the effects of that three day span. In 2005, Foulke struggled right out of the gate, posting a 6.55 April ERA. When booed, Foulke reacted with his famous Johnny from Burger King statement that fans had the right to boo if they wanted, that he was more accountable to his teammates. A few weeks later, Foulke lost his closer job to Mike Timlin, saving just 15 games on the season with a 5.91 ERA. Foulke did not pitch in the brief 2005 postseason for the Red Sox. In 2006, he was just another option in the bullpen.

Foulke was certainly not popular when left Boston after the 2006 season. His 3.77 ERA and 47 saves for the team are not spectacular numbers by any means, but without his efforts in 2004, it is not likely the Red Sox would have broken through, so to this writer, his contract was more than worth it.

Next: Bill Mueller

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Bill Mueller

The signing of Bill Mueller to a three-year, $6.7 million deal flew under the radar considering he was at the time a 32-year old third baseman coming off of a down season, but he quickly proved himself to be a tremendous bargain.

Mueller hit .326 in his first season in Boston to capture the AL batting title, while also setting career highs with 45 doubles and 19 home runs. The career .291 hitter always had a penchant for getting on base, but he saved some of his best work for Boston.

His Red Sox career was highlighted by several significant moments. On July 29, 2003 against the Texas Rangers the switch-hitter became the first player in history to hit two grand slams in the same game from opposite sides of the plate. Nearly one year later, Mueller hit a walk-off home run against Mariano Rivera to beat the Yankees on a day often remembered as the game that saw both benches clear, with catcher Jason Varitek shoving his mitt in the face of Alex Rodriguez. Many consider that the turning point in Boston’s season, which would end with a championship title. Mueller wasn’t done with Rivera yet though. Everyone remembers the infamous Dave Roberts steal in Game 4 of the 2004 ALCS, but it was Mueller that drove him home to tie the game, sparking the most epic comeback in sports history.

That clutch RBI may have been the highlight of Mueller’s postseason career, but we can’t overlook that he went 6-for-14 (.429) and drove in another pair of runs in the World Series that year.

Mueller’s time in Boston was fairly brief, but remarkably memorable. He compiled 10.0 WAR over his three seasons with the Red Sox, while earning just over $2 million per year. As far as veteran free agents go, you won’t find many better bargains than that.

Next: Johnny Damon

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Johnny Damon

Two home runs, including a grand slam, in Game 7 of the ALCS. That will forever be my highlight memory of Johnny Damon, but there was significantly more to his Red Sox career that lasted just four seasons, including a memorable three hits in one inning against the Marlins in 2003.  

In 2002 Damon made the All-Star team as a centerfielder and also finished the season leading the AL in triples.  In 2005 he made his second All-Star appearance and tallied a league-leading 35 infield hits.  During his Red Sox tenure, Damon was almost exclusively a lead-off hitter with a .295 average and impressive .362 OBP.  Damon could motor and registered 98 steals as a member of the Red Sox, scoring over 100 runs in each season in Boston.

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Damon displayed a very questionable arm but was excellent at charging a ball and covering the gaps. A fearless defender who most notable suffered a concussion via an on-field collision with Damien Jackson. Damon felt every ball was a potential out and would pursue with reckless abandon.

Damon presented a flamboyant appearance with his long hair, infectious smile, and hard style of play. Damon was certainly a fan favorite with the female members of Red Sox Nation. And, of course, Damon was probably the most symbolic member of the self-proclaimed “Idiots” who led the Red Sox to the exorcism of “The Curse.” A game was never without Damon’s acolytes dressed in robes and sporting long hair in honor of their hero.

Damon departed the Red Sox when the New York Yankees were willing to go to four years on a contract instead of the three years the Red Sox were holding firm on. But the legacy of that 2004 team and Damon’s four years of quality production will always have his contract as a free agent bargain.  

Next: John Lackey

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John Lackey

Theo Epstein and the Boston Red Sox officially signed John Lackey to a five-year, $82.5 million dollar deal in December of 2009. Lackey was largely considered the best free agent pitcher on the market that offseason, and adding his arm to a rotation that already included Jon Lester and Josh Beckett made Boston a serious contender for best rotation in the league.

Lackey was coming off a few very solid seasons for the Angels, however things didn’t exactly go as planned right away in Boston. He was really just mediocre in his first season in a Sox uniform going 14-11 and a 4.40 ERA. Then in 2011, in the midst of a mega collapse that would see the Sox get knocked out of the playoffs in the final weeks of season, Lackey would find himself amongst the players in the “chicken and beer” controversy which the fans said symbolized Boston’s nonchalant attitude. Lackey would go on to miss all of 2012 after having Tommy John surgery in the offseason.

After those three seasons, it would be logical to step back and ask how Lackey finds himself on this list. Well, everyone loves a good story of redemption, and that’s just what happened in 2013. Lackey returned as the number two starter behind Lester and provided a steady, reliable arm with veteran leadership that helped lead the Sox to become World Series champs. In many fans’ eyes, his contribution to a world champion team erased all of the ill will that had snowballed over the prior few seasons.

Lackey was solid in 2014 as well, but in the final year of his deal with the Sox tumbling to last place, the team decided to part ways at the trade deadline in a deal that sent Lackey to St. Louis. Still, that 2013 tam that caught lightning in a bottle was a lovable bunch, and John Lackey was a big reason for their success. You can’t argue with champions.

Next: Mike Napoli

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Mike Napoli

The Red Sox initially agreed to a 3-year, $39 million deal with Napoli, but the discovery of a rare hip condition during his physical complicated matters. Napoli ultimately agreed to a one-year deal with incentives that could reach the $13 million he was originally expected to be paid, with the understanding that if he remained healthy and productive then he would be extended for the other two years of the original agreement.

Napoli’s hip condition proved to be no issue in 2013. While the former catcher was no longer able to spend time behind the plate, he completed a smooth transition to being a full-time first baseman. Napoli hit .259/.360/.482 with 23 home runs and 92 RBI in his first season with the Red Sox, easily living up to the value of that one-year deal.

2013 saw the Red Sox deliver another championship, which Napoli played a significant role in. He blasted a pair of home runs in the ALCS against the Detroit Tigers, including one in Game 3 against Justin Verlander that proved to be the only run of the game in Boston’s 1-0 victory.

After proving himself on his one-year deal, the Red Sox rewarded Napoli with a 2-year, $32 million deal, ultimately earning him more money than his original three-year deal would have been worth. This second contract didn’t turn out nearly as well, as injuries limited Napoli to 119 games in 2014, while his OPS fell from .842 to .789. His production fell off a cliff the following year when Napoli hit a mere .207 in 98 games before being shipped to Texas before the trade deadline.

Over the three years Napoli spent in Boston, he really only had one good year. If we look at only that initial one-year deal the Red Sox gave him in 2013, he turned out to be a great free agent find. Given his contributions to a World Series title, that more than makes up for the dwindling production over the next year and a half. In the end it was worth it to have a shirtless Mike Napoli stumbling around the streets of Boston in search of the next spot where he could celebrate being a champion.

Next: Shane Victorino

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Shane Victorino

Just over a week after the Red Sox had reached their initial agreement with Napoli on a three-year deal, the Red Sox signed Shane Victorino to an identical $39 million deal. Unlike Napoli, Victorino had no pre-existing medical issues that forced the Red Sox to alter the terms of the agreement. However, just as was the case with Napoli, Victorino had an outstanding 2013 season, followed by two injury plagued years that derailed the rest of the contract.

Victorino hit .294/.351/.451 in 2013 and earned a Gold Glove award for his outstanding play in Fenway’s difficult right field. The Flyin’ Hawaiian quickly established himself as a fan-favorite and proved to be a vital cog in the team’s championship that season. In the seventh inning of Game 6 of the ALCS, Victorino smashed a game-winning Grand Slam over the Green Monster to defeat the Tigers, sending Boston to the World Series.

A number of injuries limited Victorino in 2014 and he eventually was shut down due to season-ending back surgery after appearing in only 30 games. He would return with the Red Sox the following season, but a nagging hamstring injury landed him back on the disabled list. Victorino played only 33 games for the Red Sox last season before being traded to the Angels.

Victorino essentially earned his entire $39 million in one great season, so don’t worry about how it ended, be happy with what he helped this team accomplish in 2013. In the end, every little thing turned out all right.

Next: Adrian Beltre

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Adrian Beltre

Adrian Beltre rode a monster 2004 season with the Dodgers to a lucrative contract with the Seattle Mariners, but a move to one of the game’s most pitcher-friendly parks put a damper on the power that got him paid big bucks to begin with. His home run total fell from 48 to 19 in his first year in Seattle, while his batting average and RBI totals plummeted as well. When Beltre hit the free agent market again after the 2009 season he knew he could’t command the same type of money after being labeled a bust, so he went out seeking a one-year “prove it” deal to restore his value.

He found that deal with the Red Sox, who signed him to a 1-year, $9 million deal for the 2010 season. Beltre’s plan worked perfectly, as the move to Fenway woke up his bat and reminded the league that he is among the best third basemen in the league. He hit .321 with 28 home runs, 102 RBI and a league-leading 49 doubles in his only season with the Red Sox. Beltre made his first career All-Star appearance that season, winning a Silver Slugger and finishing 9th in MVP voting.

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Beltre made a lot of fans in Boston for what he produced in his bounce back campaign, but it wasn’t enough to keep him in town. The Red Sox were enamored with San Diego Padres first baseman Adrian Gonzalez and moved quickly to assemble a package of prospects to trade for him. The front office wasn’t willing to invest heavily in both corner infielders, especially since they still had fan-favorite Kevin Youkilis on the roster, so they essentially picked Gonzalez over Beltre.

After the Red Sox let him walk away, Beltre signed a 6-year, $96 million deal to join the Rangers. At the time it seamed reasonable to invest in the younger Gonzalez, yet here we are today with the 36-year old Beltre entering the final year of his deal and still putting up All-Star caliber numbers. Meanwhile, Gonzalez lasted only a year and a half in Boston before being shipped to the Dodgers in a blockbuster trade that cleared a quarter of a billion dollars in salary from the Red Sox payroll.

Third base has been a bit of a black hole since Beltre left, culminating in the Red Sox overpaying Pablo Sandoval to fill the position in 2015 in what is quickly becoming one of the worst free agent deals in franchise history. Perhaps they would have been better off keeping Beltre after all.

Next: Koji Uehara

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Koji Uehara

When the Red Sox signed Koji Uehara to a 1-year, $4.25 million deal prior to the 2013 season they expected him to be a middle reliever, until injuries to Andrew Bailey and Joel Hanrahan unexpectedly thrust him into the closer role. As it turned out, that was the best thing that could have happened for that Red Sox team.

Uehara was brilliant in his first year in Boston, collecting 21 saves and posting a spectacular 1.09 ERA. Between July 9 and September 17, Uehara retired a franchise record 37 consecutive batters and would finish the season with a 0.56 WHIP to set a major league record for pitchers with a minimum of 50 innings pitched.

He was also outstanding in the postseason, allowing only 1 run in 13.2 innings during Boston’s run to a World Series title in 2013. Uehara collected 7 saves during that postseason and was named MVP of the ALCS.

While it’s unreasonable to expect those historic numbers again, Uehara has remained one of the game’s best relievers when healthy. Unfortunately this past season did not end that way, with Uehara finishing the year on the disabled list with a fractured wrist. The veteran will turn 41 years old next season and will need to have his innings managed more carefully. With Craig Kimbrel being brought in to take over in the ninth inning, Uehara will be counted on to handle the set-up role he was originally brought here for.

Red Sox fans will still get the opportunity to celebrate Koji Time next season, but it will come an inning or two earlier than it used to.

Next: Manny Ramirez

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Manny Ramirez

When Manny Ramirez hit the free agent market after the 2000 season he was coming off a season in which he finished third in MVP voting and delivered a league-leading 1.105 OPS. That production earned him an 8-year, $160 million contract from the Red Sox, which was at the time the most lucrative contract in franchise history.

Ramirez never failed to produce during his seven and a half seasons in Boston, as he established himself as one of the best right-handed hitters of his generation. He made the All-Star team in every season he spent with the Red Sox and finished in the top-10 in MVP voting in each of his first five seasons here in Boston. Smashing 30+ homers and driving in over 100 RBI was like clockwork for Ramirez, who became the anchor of one of baseball’s best offenses.

As long as Ramirez was producing at the plate, the Red Sox were willing to overlook his poor defensive instincts and goofy antics. Taking a bathroom break inside the Green Monster during a pitching change, showing up late to Spring Training, or diving to cut off a throw that wasn’t intended for him? That’s just Manny being Manny.

Eventually Manny’s act wore thin, paving the way for his exit from Boston in the summer of 2008. Ramirez’s production began to dip as he complained of leg pain in order to excuse himself fro the lineup, despite occasionally forgetting which leg was supposed to be the injured one. Needless to say, his teammates weren’t thrilled, which boiled over into a heated argument with Kevin Youkilis that resulted in Ramirez taking a swing at him in the dugout. Weeks later the final stroke broke when Ramirez shoved Red Sox traveling secretary Jack McCormick to the ground during a dispute over tickets. The Red Sox traded Ramirez at the deadline to the Los Angeles Dodgers as part of a three-way trade that landed Jason Bay in Boston.

It often ends badly when a star player leaves town, but it’s hard to fathom an uglier divorce than the one the Red Sox had with Ramirez. Despite how it ended, Ramirez still proved to be one of the game’s best hitters while he was here and helped the Red Sox win a pair of championships, including the curse-breaking 2004 title in which Ramirez was named World Series MVP. Regardless of what you may think about Manny being Manny, his production clearly lived up to his lofty price tag.

Next: David Ortiz

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David Ortiz

David Ortiz has had a prolific career, but he didn’t become the Big Papi we know today until he arrived in Boston.

In the early stages of his career Ortiz spent parts of six seasons with the Minnesota Twins as a part time first baseman and DH. While the power in his bat was evident even in those days, he was still considered an injury prone player without a position with massive holes in his swing against left-handed pitching. The Twins designated Ortiz for assignment after the 2002 season after failing to find a team willing to trade for him.

The Red Sox picked Ortiz up off the scrap heap despite not having a clear path to playing time available, signing him to a 1-year, $1.25 million deal. He played sparingly in the first couple months of the 2003 season, but would soon force his way into the everyday lineup as the DH. Ortiz would end up hitting 31 home runs and driving in 101 RBI in his first season in Boston, while finishing fifth in MVP voting. Suffice it to say, the Twins immediately regretted letting him get away.

The rest, as they say, is history. During his time in Boston Ortiz has won three championships, made 9 All-Star appearances, won 6 Silver Slugger awards and finished in the top-10 in MVP voting six times. His postseason heroics are legendary and last season he added another milestone to his career by joining the 500 Home Run club.

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Ortiz ended his tenure in Minnesota having been cast aside as a flawed hitter that nobody wanted. He’ll end his career in Boston as the greatest designated hitter to ever play the game on a path to Cooperstown.

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