Who is the highest-paid player in Red Sox history?

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Since the group led by John Henry and Tom Werner purchased the Boston Red Sox in 2002, the franchise generally hasn’t been afraid to spend money.

The ownership group delivered on its goal of breaking the Curse of the Bambino in 2004, but it didn’t stop there. Theo Epstein, Ben Cherrington and Dave Dombrowski each handed out their share of lucrative contracts over their tenures in the front office. Some worked out and some didn’t, but winning World Series rings was always the goal. The four championships that Boston has won since 2004 all came at a steep cost.

Here are the top five players who have earned the most total cash for the Red Sox:

5. Pablo Sandoval

Total cash: $95,455,000

This is one that Red Sox fans want to forget. Sandoval signed a five-year, $90 million deal with Boston before the 2015 season after winning three World Series titles with the San Francisco Giants (2010, 2012, 2014). He only played 161 games across two-plus seasons in Boston.

The Red Sox cut Sandoval in 2017 after 32 ugly games (.212/.269/.354), as they were forced to eat the remaining two-plus years on his contract plus his $5 million buyout. The final $5 million was paid out in 2020, so the Red Sox are officially done paying the Panda.

4. Dustin Pedroia

Total cash: $122,053,721

Fans will have much fonder memories of the man just ahead of Sandoval. Pedroia was the heart and soul of the Red Sox for the duration of his 14-year playing career. He signed only two major contracts in his career -- the first a six-year, $40.5 million deal in 2008, the second an eight-year, $110 million extension in 2013. The Laser Show didn’t make it to the final year of his final extension, as he retired before the 2021 season due to chronic knee injuries.

The Red Sox will pay Pedroia $2 million per year from 2022 to 2024 and $2.5 million per year from 2025 to 2028 due to deferred payments. That will ultimately make his Red Sox earnings total $138,053,721. Every dollar was worth it for the 2008 AL MVP and two-time World Series champion.

3. David Price

Total cash: $137,000,000

Price was the first major signing of the Dave Dombrowski era in 2016. His seven-year, $217 million deal was the largest in team history, though he wasn’t able to finish it out in Boston. The Red Sox included Price in the Mookie Betts trade to the Dodgers, freeing them of $64 million from Price’s contract. Boston will still pay Price $16 million in 2022, bringing his Red Sox total cash to $153 million.

Over his four seasons with the Red Sox, Price was a perennially solid pitcher. He never quite lived up to his Red Sox contract, but there was no denying the stability he brought to the rotation. Price went 46-24 with a 3.84 ERA in 103 regular season games. The lasting memory of Price in Boston was the 2018 postseason, where he delivered a 2-0 record with a 1.98 ERA in two World Series starts for the champions.

2. David Ortiz

Total cash: $158,962,500

The most clutch hitter in franchise -- and perhaps MLB -- history, Ortiz probably should’ve earned more money in his Red Sox career. Big Papi never signed a massive long-term deal with the Red Sox despite playing 14 years with the club. Instead, he lived off of short-term deals over the final five years of his career. The four-year, $52 million deal Ortiz signed in 2006 was his only deal longer than two years. Ortiz earned $16 million per year in his final two seasons, the highest single-season salary of his career.

As a result of his short-term deals, Boston doesn’t owe Ortiz any deferred money in his retirement. He went out in his final season in 2016 and delivered one of his best ever with  a league-leading 48 doubles, 127 RBIs and 1.021 OPS. The three-time World Series champion already has his number retired and will always be a living legend in Boston.

1. Manny Ramirez

Total cash: $165,827,228

The second half of the Red Sox’s power hitting duo of the 2000s tops his friend despite only playing eight seasons in Boston. Ramirez signed an eight-year, $160 million deal with Boston before the 2001 season after eight years with the Cleveland Indians. The 2004 World Series MVP helped deliver two titles for the Red Sox.

As the highest-paid Red Sox player, Ramirez was well worth the money before being traded to the Dodgers in 2008. He had 274 home runs and hit .312/.411/.588 over 1,083 games with the Sox. As a result of the trade, Boston has been and will continue to pay Ramirez around $2 million per year until 2026. His total earnings will eventually rise to $175,995,432 once his deferred salaries are paid out over the next five years.

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