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What are the biggest contracts in Red Sox history?

Rafael Devers now has the largest contract, in terms of value, in Red Sox history.John Tlumacki/Globe Staff

The departures of Xander Bogaerts and Mookie Betts have cultivated a narrative that Red Sox leadership is unwilling to open up their checkbooks to retain or add talent.

Boston countered that stance on Wednesday with its 11-year, $331 million contract extension for Rafael Devers.

Devers’s megadeal is the most expensive contract ever doled out by the Red Sox. But it is just one of several contracts in the triple-digit millions.

So, which other players are featured on the list of the largest contracts in Red Sox history?

Let’s dive in.

10: P Daisuke Matsuzaka — 6 years, $103.1 million

Matsuzaka is an interesting case. His deal with Boston was a six-year, $52 million agreement struck in December 2006. But the Red Sox also had to spend $51.1 million as a posting fee in order to gain exclusive negotiating rights with the Japanese ace , leading to the final triple-figure payout.

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A pitching sensation with the Seibu Lions during his time with the Nippon Professional Baseball league, Matsuzaka was expected to be a No. 1 starter for the Red Sox — with his legendary “gyroball” pitch destined to befuddle batters in MLB.

Of course, Matsuzaka did help the Red Sox win the 2007 World Series (15-12, 4.40 ERA in his MLB debut season), but the righty failed to live up to expectations. Even his best season with the Sox (2008: 18-3, 2.90 ERA) was marked by short outings and extended pitch counts.

In six seasons with Boston, Matsuzaka went 50-37 with a 4.52 ERA and a 1.41 WHIP. He played two more seasons in North America with the Mets (2013-14) before finishing his career back in Japan.

9 (tie): 2B Dustin Pedroia — 8 years, $110 million

When Pedroia signed off on a $110 million contract extension with Boston back in July 2013, the franchise infielder was only the second second baseman in MLB to cross the $100 million threshold with a new deal.

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But even back then, Pedroia’s lengthy contract was considered a bargain move, a sign of Pedroia opting for long-term security over a more lucrative deal on the open market.

Pedroia had already put together an impressive resume by 2013 — winning a World Series and Rookie of the Year in 2007, an AL MVP trophy in 2008, and had posted a career batting average of .303t.

Pedroia further rewarded Boston’s faith in him by helping the Red Sox win another World Series in 2013, batting .301 with nine home runs and 84 RBI over 160 games.

That represented a high point of Pedroia’s new contract. A dirty slide by Orioles infielder Manny Machado in 2017 injured Pedroia’s knee, and the Sox star appeared in only nine games from 2018 until he retired in 2021.

9 (tie): DH J.D. Martinez – 5 years, $110 million

Martinez’s contract was validated with his 2018 season. With Boston in desperate need of a slugger in the heart of the lineup to replace David Ortiz, Martinez was a hitting machine — batting .330 with 43 home runs and a league-leading 130 RBIs. He finished fourth in AL MVP voting.

Martinez hit .300 with three home runs and 14 RBIs in 14 postseason games en route to a World Series title. In his five seasons with Boston, Martinez earned four All-Star nods and drove in 423 runs.

8: SS Xander Bogaerts — 6 years, $120 million

Well, this one aged poorly.

Bogaerts’s six-year extension with the Sox inked in April 2019 was considered a below-market win for Boston, but an opt-out clause in 2022 opened the door for the shortstop to drive up his price if he continued to thrive at the plate.

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Sure enough, Bogaerts continued to live up to his end of the bargain —.304 batting average, 82 home runs and 297 RBIs from 2019-22 — opening the door for him to join a crowded field of star free-agent shortstops this offseason.

It was a good move for Bogaerts (and his agent, Scott Boras). Bogaerts signed an 11-year, $280 million contract with the San Diego Padres last month.

7: SS/2B Trevor Story — 6 years, $140 million

Boston went out and signed Trevor Story in March 2022 following a productive stretch out in Colorado.

The verdict isn’t in on Story yet, but the infielder didn’t live up to expectations during the 2022 season. While Story’s defense at second was impressive, his performance at the plate left a lot to be desired.

Story only appeared in 94 games , batting .238 with 16 home runs and 66 RBIs while striking out 122 times in 357 at-bats.

6: OF Carl Crawford — 7 years, $142 million

When the Sox pried Crawford out of Tampa Bay back in the winter of 2010, they thought they had their leadoff man of the future — a dynamic player capable of impacting games at the plate, in the field, and on the basepaths.

But the move proved to be a disaster. Crawford struggled at the plate and never quite acclimated to the big-market atmosphere and pressure in Boston. He played just 161 games over two seasons, batting .260 with a .292 on-base percentage, before he was dealt to the Dodgers in 2012.

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5: P Chris Sale — 5 years, $145 million

Chris Sale’s first two seasons with the Red Sox were dominant — the lanky southpaw went 29-12 with a 2.56 ERA over 59 starts from 2017-18, while striking out 545 batters over 372⅓ innings of work. He finished second in AL Cy Young voting in 2017, and helped Boston win a World Series in 2018.

But after Boston rewarded Sale with a five-year contract extension in 2019, the pitcher’s tenure with the Sox has been a complete disaster. Over the last four seasons, Sale has only appeared in 36 games, missing the entire 2020 season due to Tommy John surgery.

The 2022 season was a particularly brutal stretch for both Sale and the Sox. The ace only logged 5⅔ innings of work after being sidelined with a myriad of injuries: a fractured rib, a fractured pinky finger, and a broken wrist following a bicycle accident.

If Sale doesn’t right the ship, this could stand as the most disastrous contract in Sox history, a startling end for a pitcher who was close to unhittable over his first two seasons in a Sox jersey.

4: 1B Adrian Gonzalez — 7 years, $154 million

The Red Sox paid a king’s ransom to acquire Gonzalez from the Padres in 2010, dealing top prospects Casey Kelly, Anthony Rizzo (ouch), and Reymond Fuentes to San Diego in exchange.

After Gonzalez to the lineup, Boston managed to keep him long-term with a seven-year extension signed shortly after the 2011 season began. Gonzalez was effective in his debut season with Boston, leading the AL in hits (213), batting .338 and winning a Gold Glove.

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But with the Sox in need of a reset, they sent Gonzalez to the Dodgers in August 2012 in a deal that had LA take on the contracts of Josh Beckett, Carl Crawford, and Nick Punto.

The trade allowed Boston to retool ahead of its 2013 World Series title.

3: LF Manny Ramirez — 8 years, $160 million

Ramirez’s megadeal stands as the third-largest contract in Red Sox history, even though it was signed more than two decades ago.

And even though Ramirez last played with Boston back in 2008, the Sox are still paying the slugging left fielder through a deferred payment plan. The last payout is scheduled for 2026, when Ramirez will be 54.

But this was a move that paid for itself. The Red Sox’ decision to spend meant the team had an impact bat in the middle of the lineup. Ramirez, alongside David Ortiz, gave the Red Sox one of the best 3-4 duos in recent memory.

Along with his impressive individual accolades (.312 batting average, .999 OPS, 274 home runs, 868 RBI), Ramirez helped the Red Sox win two World Series. He helped snap the 86-year championship drought while winning World Series MVP in 2004.

2. P David Price — 7 years, $217 million

Price’s tenure in Boston was rocky.

Price’s deal in January 2015 was the largest contract for a pitcher in MLB history. But he failed to live up to expectations in his first few seasons, with injuries and underperformance marring his early tenure.

Price redeemed himself in 2018, going 16-7 with a 3.58 ERA over 30 starts during the regular season before helping Boston win a World Series. Steve Pearce took home World Series MVP honors, but it could have easily been Price (two wins, three earned runs over 13⅔ innings of work).

The Red Sox dumped Price’s contract in the deal that sent Mookie Betts to the Dodgers in February 2020. Los Angeles took on $64 million over the final three seasons of Price’s contract. Boston still paid him $16 million in 2022.

1: 3B Rafael Devers — 11 years, $331 million

Devers’s new deal blows everyone else out of the water. In terms of total value, it is the sixth-largest in MLB history.

1. Mike Trout, Angels: $426.5 million (2019-30)

2. Mookie Betts, Dodgers: $365 million (2021-32)

3. Aaron Judge, Yankees: $360 million (2023-31)

4. Francisco Lindor, Mets: $341 million (2022-31)

5. Fernando Tatis, Padres: $340 million (2021-33)

6. Rafael Devers, Red Sox: $331 million (2023-34)