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.

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.

Crawford couldn’t handle the pressure of playing for the Red Sox

Carl Crawford spent the first nine years of his career terrorizing the Red Sox as a member of the Tampa Bay Rays. Signing the four-time All-Star to a seven-year, $142 million deal was as much about taking away from a division rival as it was adding to their own roster. He can’t do damage to our club if he’s one of us, right?

They couldn’t have been more wrong. Crawford did plenty of damage with his underwhelming production on the field and with his attitude in the clubhouse.

Crawford set a career-low with a .255 batting average during his first season in Boston while his .694 OPS was the lowest he produced since his first full season in the big leagues.

Speed was always a vital part of Crawford’s game. He swiped 46+ bases in seven of his first eight full seasons, topping 50 steals four times and reaching 60 once. Crawford stole only 18 bags for the Red Sox in 2011.

Crawford was once viewed as a strong defensive outfielder who earned a Gold Glove in 2010 but as soon as he arrived in Boston, he immediately became below-average with -1 defensive runs saved.

An epic September collapse by the Red Sox was sealed by Robert Andino’s walk-off base hit against Jonathan Papelbon in the final game of the regular season. Crawford made a half-hearted slide that came up short on the line drive to left and followed with an off-target throw that failed to beat the runner scoring the game-winning run. It would have been a great play if Crawford had made the catch but it still felt like he misplayed it, costing his team a trip to the postseason.

Crawford never seemed comfortable in Boston and many questioned if he could handle the pressure of playing in a big market after thriving for the small-market Rays. He became a malcontent who contributed to a toxic clubhouse environment that eventually forced the Red Sox to make a drastic roster overhaul.

In August of 2012, the Red Sox made a blockbuster trade with the Dodgers to send Crawford, Josh Beckett, Adrian Gonzalez and Nick Punto to Los Angeles. Gonzalez was the target for the Dodgers but the Red Sox insisted that they take Crawford and Beckett off their hands, removing their bloated contracts from the payroll and their poor attitudes from the clubhouse.

The financial freedom created by the trade enabled the Red Sox to rebuild their roster in 2013 around high-character veterans, leading to an improbable worst-to-first turnaround and a World Series title.

About a year and a half of disappointing production isn’t what you expect when you sign a free-agent to a contract that, at the time, was the highest average annual value in franchise history. Boston got lucky that the Dodgers were wiling to take their salary dump, even if it cost them their All-Star first baseman.

Celebrating a championship in 2013 washed away much of the bitterness from the dysfunctional Red Sox teams that preceded that magical season but we’ll never completely be able to forget about the expensive mistake that Crawford turned out to be.