5 worst free-agent contracts in Boston Red Sox history

The Red Sox have made some horrible decisions in free agency

Money doesn’t solve everything. Throwing buckets of cash at the top free-agents might seem like the simple solution but the strategy can backfire. The Boston Red Sox know that all too well with a history littered with poor investments.

Major League Baseball is structured in a way that vastly underpays their top stars early in their careers and prevents them from cashing in through free agency until they’ve already reached their peak. The best free-agents are going to command top dollar on long-term deals that will continue paying them to be stars long after their skills start to erode. That’s the nature of the beast. In order to land the top talent in free agency, teams must be willing to risk overpaying on the back end of deal. For teams that can afford to pay up, the process is typically worthwhile as long as the player performs to expectations for the majority of the contract.

Sometimes that decline comes early, turning a lucrative contract into an albatross long before the team was able to get their money’s worth. In some cases, the player never lives up to expectations.

There are several factors to explain why the Red Sox didn’t join the spending spree that captured headlines leading into the lockout. While we expect the team to make more moves once a new CBA is in place, they don’t necessarily need to be flashy. Spending recklessly in an effort to “win” the offseason doesn’t guarantee a championship and spending on the wrong players can be detrimental to that goal.

Let’s take a look back at some expensive deals the Red Sox have handed out to former All-Stars in free agency that backfired with disastrous results.

Lackey left the Red Sox rotation lacking

The Red Sox signed John Lackey to a five-year, $82.5 million deal prior to the 2010 season. The idea was to form a dominant trio at the top of the rotation alongside Josh Beckett and Jon Lester but the plan didn’t pan out as well as expected.

Lackey spent the first eight seasons of his career with the Los Angeles Angels, notching 102 wins while posting a 3.81 ERA. He peaked in 2007 when he won 19 games with a league-leading 3.09 ERA to earn an All-Star appearance and a third-place finish on the AL Cy Young award ballot.

While he looked the part of an ace during his prime years with the Angels, he performed more like a back of the rotation starter when he arrived in Boston. In 2010, Lackey went 14-11 with an underwhelming 4.40 ERA and a 6.5 K/9 that was his lowest strikeout rate since he was a rookie.

He followed that with a miserable season in which he produced a career-worst 6.41 ERA, led the league with 114 earned runs, and saw his strikeout rate dip to 6.1 K/9 while his walks increased to a career-worst 3.2 BB/9. Lackey’s struggles contributed to Boston’s historic collapse that season and he was a member of the infamous Chicken & Beer club that embarrassed the organization.

Tommy John surgery wiped out Lackey’s third season in Boston but he bounced back strong in 2013. Despite a losing record (10-13), Lackey produced a 3.52 ERA, 7.7 K/9 and 1.9 BB/9 that was more in line with what the Red Sox were expecting when they signed him. He was solid in the postseason, helping the Red Sox capture a World Series title.

Lackey had a unique clause in his contract that included a 2015 team option at the minimum salary if the righty missed significant time to a pre-existing elbow injury, which is what led to him undergoing Tommy John surgery. Getting Lackey for a bargain price for an extra year would have helped offset the first three miserable seasons he spent in Boston, especially since he was pitching well again post-surgery. Unfortunately, Lackey made it clear that he wasn’t interested in pitching for a minimum salary. There were rumors that he would threaten to retire if Boston tried to hold him to that commitment.

The Red Sox needed to hit the reset button following a disappointing start to the 2014 season. Rather than risk an ugly confrontation with Lackey over his contract, Boston dealt him to the St. Louis Cardinals at the trade deadline for Allen Craig and Joe Kelly.

Craig was an All-Star in 2013 and made a strong impression during St. Louis’ World Series loss to Boston but he was never the same after a foot injury derailed his career. He hit a pitiful .139 with a .432 OPS in 65 games over two seasons with the Red Sox until he was mercifully released.

Kelly had his moments in Boston and established himself as a fan-favorite but he failed to deliver as the starting pitcher they hoped would replace Lackey. He found his groove when he moved to the bullpen but wasn’t quite as valuable in that middle relief role.

Meanwhile, Lackey agreed to play for the Cardinals under the same minimum contract he supposedly refused to honor in Boston. He had an excellent year in St. Louis, going 13-10 with a 2.77 ERA.

Lackey was a poor free-agent signing due to being unproductive or injured for the first three years of the deal. He doubled-down on making the signing a poor decision by essentially forcing a trade that stuck the Red Sox with Allen’s horrible contract.

David wasn’t worth the Price for the Red Sox

The Red sox needed a spark to energize the club in the wake of consecutive last-place finishes. Inking former Cy Young award winner David Price to a seven-year, $217 million deal, the richest contract ever given to a pitcher at the time, certainly changed the outlook for the team heading into the 2016 season.

Price wasn’t terrible in his first year in Boston but he was still viewed as a disappointment based on his reputation and massive salary. He won 17 games and led the league with 230 innings but his 3.99 ERA was by far the highest it had been since his rookie season.

His numbers improved during his second season in Boston but everything else about 2017 was a disaster. An elbow injury in spring training delayed his debut until Memorial Day and sent him back to the injured list in July, limiting him to 11 starts. Price clashed with the media, berated a reporter after a game at Yankee Stadium and had a much-publicized confrontation with Hall of Fame pitcher and NESN analyst Dennis Eckersley.

Price dialed down his erratic behavior while delivering his best performance in a Red Sox uniform in 2018. He went 16-7 with a 3.58 ERA and 9.1 K/9. He followed that with a strong postseason and arguably should have been the World Series MVP, tossing 13 2/3 innings over three appearances while allowing only three earned runs for a 1.98 ERA against the Los Angeles Dodgers.

His postseason heroics helped wash away the bitter taste from the previous two years but Price’s redemption story wouldn’t last. A promising 2019 season unraveled when Price developed a cyst on his left wrist. He tried pitching through the ailment but failed to command most of his pitches due to the lack of mobility in his wrist. Price was shelled for 20 runs over his next four starts for a brutal 10.59 ERA. He landed on the injured list and made only one more brief appearance in early September before the Red Sox shut him down again.

While he never performed to the level that his contract demanded, Price proved that he could still be a very capable starter when he was healthy. The problem was that he wasn’t healthy often enough. Combine that with a prickly attitude that rubbed fans the wrong way and it’s clear why Price was never fully embraced in Boston.

The Red Sox were desperate to shed salary in order to reset the dreaded luxury tax penalties and unloading Price’s massive contract was the simplest path to financial freedom. Unfortunately, the cost for moving Price was Mookie Betts. Boston’s reasons for trading the former MVP is a whole other can of worms but they willingly accepted a lesser haul in return because the Dodgers agreed to take Price and half of his remaining contract off their hands. Boston is stuck paying $16 million per year through the 2022 season for Price to pitch in a Dodgers uniform.

Hanley’s homecoming disappointed the Red Sox

Hanley Ramirez came up through the Red Sox farm system and briefly made his major league debut in 2005 before headlining a trade package that sent him to the Marlins in exchange for Josh Beckett and Mike Lowell. The deal would ultimately lead to a World Series title for the Red Sox in 2007 while Ramirez would flourish in Florida.

Ramirez returned to the Red Sox when they signed him to a four-year, $88 million deal prior to the 2015 season. Unfortunately, he failed to live up to the reputation he built over a decade in the National League.

A hot start to his first season back in Boston had fans excited about the reunion. Ramirez blasted 10 home runs in the month of April, leading the team to a winning record in the opening month of the season.

In early May, Ramirez suffered a shoulder injury when he collided with the left field wall while chasing a fly ball. He tried to battle through the pain but clearly wasn’t the same hitter and was shut down in late-August with a sore shoulder. Ramirez finished the season hitting .249 with a .717 OPS, 19 home runs and 53 RBI.

The offensive production wasn’t horrible but it was far from the level the Red Sox were paying him for. What’s worse is that the signing made little sense to begin with. Ramirez started his career as a shortstop but moved to third base when age sapped him of his range. The Red Sox didn’t have an opening at either position but coveted his bat enough to sign him anyway, assuming they’d figure out the fit later.

They never did. Boston’s experiment with Ramirez in the outfield was a disaster. He produced a brutal -14 defensive runs saved in only 92 games in left field. Fielding a position he wasn’t familiar with can partially be blamed on the injury that spoiled his season.

His disappointing production at the plate combined with his adventures in the outfield produced a career-worst -0.7 WAR during his first season back in Boston.

A healthy Ramirez bounced back in 2016, hitting .286 with a .866 OPS, 30 home runs and 111 RBI. He primarily played first base that season and while he wasn’t very good at it, Ramirez was less of a liability there than he was in the outfield. As long as he was producing at the plate, the Red Sox could live with his defensive limitations.

The redemption wouldn’t last. Ramirez took over the DH role in 2017 following the retirement of David Ortiz but his production declined without Big Papi’s presence in the lineup. Ramirez hit .242 with a .750 OPS, 23 home runs and 62 RBI while producing -0.3 WAR.

The Red Sox signed J.D. Martinez to be their primary DH in 2018 and Mitch Moreland was locked in at first base. Ramirez shared time at both spots early in the season but was released in May. There were concerns that Ramirez wouldn’t adapt well to a bench role and the team didn’t want to risk disrupting the clubhouse chemistry. Releasing him also avoided any chance of triggering his $22 million vesting option for 2019.

Boston ended up getting one strong season, two duds, plus one where they essentially paid him to go away.

The Panda became a liability to the Red Sox

While the Red Sox were brining Hanley back to Boston, they were also working on finalizing a five-year, $95 million deal with Pablo Sandoval. At the time, both free-agents had some appeal as arguably the best bats on the market. Sandoval lacked Ramirez’s power and didn’t have any Silver Slugger awards or a batting title on his resume. He was a two-time All-Star who won three championships and earned a World Series MVP with the San Francisco Giants though.

The problem with signing both former All-Stars is they played the same position. The addition of Sandoval led to the regrettable experiment with Ramirez in left field. This was clearly a case of the Red Sox trying to “win” the offseason with splashy signings without any regard for how they fit on the roster. Predictably, the plan backfired.

Sandoval’s first season in Boston was a disappointment, setting career-lows across the board with a .245 average, .658 OPS, 10 home runs and 47 RBI with a -0.5 WAR.

His 2016 season was cut short after only three games when a shoulder injury required season-ending surgery. The only memorable aspect of that season for Sandoval was when his belt burst during a massive swing-and-miss in a game against the Blue Jays.

The Red Sox designated Sandoval for assignment after only 32 games in 2017 in which he hit .212 with a .622 OPS while producing a career-worst -0.9 WAR. It’s difficult to provide that much negative value in such a short period of time but Sandoval found a way.

Sandoval was released in July with nearly $48 million remaining on his contract. The Red Sox were so eager to move on that they were gladly willing to eat that much salary in order prevent him from clogging a roster spot.

Injuries played a part in Sandoval’s rapid decline but his struggles were partially self-inflicted. His conditioning was a topic of concern for his entire tenure in Boston and he routinely showed up to camp out of shape. Sandoval was impressively agile for a player his size when he played for the Giants but he was immobile at the hot corner during his time in Boston and his weight began to hinder him at the plate.

Sandoval was a questionable signing from the start, especially since it coincided with adding Ramirez, but the deal turned out to be far worse than anyone could have imagined.