Red Sox: Three contract extension candidates this spring

Red Sox Chief Baseball Officer Chaim Bloom. (Photo by Billie Weiss/Boston Red Sox/Getty Images)
Red Sox Chief Baseball Officer Chaim Bloom. (Photo by Billie Weiss/Boston Red Sox/Getty Images)
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BOSTON, MA – OCTOBER 28: Chaim Bloom speaks as he is introduced as Boston Red Sox Chief Baseball Officer during a press conference on October 28, 2019 at Fenway Park in Boston, Massachusetts. (Photo by Billie Weiss/Boston Red Sox/Getty Images)
BOSTON, MA – OCTOBER 28: Chaim Bloom speaks as he is introduced as Boston Red Sox Chief Baseball Officer during a press conference on October 28, 2019 at Fenway Park in Boston, Massachusetts. (Photo by Billie Weiss/Boston Red Sox/Getty Images) /

The Red Sox might try to lock up these players with an extension

The Boston Red Sox have had a busy offseason but they aren’t necessarily done yet. While the focus has been on reshaping the roster to build depth and plug holes, the next step could be looking internally to address the future of their core players.

Chaim Bloom was addressing the media on Sunday when the topic of contract extensions was brought up. The Red Sox Chief Baseball Officer confirmed that there have been internal discussions about potential candidates and he expects to speak with those players about an extension this spring.

The San Diego Padres recently locked up Fernando Tatis Jr. with a massive 14-year, $340 million extension, ensuring their emerging young star remains with the organization through the prime of his career. This creates cost certainty for the team, financial security for the player, and provides relief for Padres fans who no longer need to worry about if the team can afford to keep their star in San Diego.

Red Sox fans who remain haunted by the departure of Mookie Betts know all too well the risks of allowing their best player to approach free agency without an extension. Securing a player’s future in Boston would avoid that unenviable scenario of trading them away before they get the chance to leave them for nothing.

On the other hand, Chris Sale’s contract is a cautionary tale about jumping the gun too early with an extension. Sale’s health wasn’t in question when he signed his five-year deal but one year and one significant arm surgery later and critics are quick to label the extension a disaster.

Contract extension negotiations can be complicated by factors that vary from player to player. It has to work for both sides and the timing needs to be right. The Red Sox will have these discussions with certain players but that doesn’t necessarily mean a deal will get done this spring.

Since we have confirmation that the team will approach certain players about an extension, let’s look at the top candidates who Bloom may have been hinting at when he confessed to having these internal discussions.

Alex Verdugo of the Boston Red Sox reacts to hitting a solo home run. (Photo by Adam Glanzman/Getty Images)
Alex Verdugo of the Boston Red Sox reacts to hitting a solo home run. (Photo by Adam Glanzman/Getty Images) /

Red Sox extension candidate – Alex Verdugo

We only have a limited sample from the shortened 2020 season but Alex Verdugo certainly impressed during his first year in Boston.

The 24-year-old was arguably the best player on the team last season, hitting .308 with an .844 OPS, six home runs, and four stolen bases in 53 games. He also provided a strong defensive presence while accepting the challenge of handling Fenway Park’s notoriously difficult right field.

As the centerpiece of the Betts blockbuster trade, the Red Sox will certainly have interest in locking up Verdugo. The Dodgers have already secured the future of Betts in Los Angeles and Boston won’t want to risk his replacement leaving after a few seasons.

With Jackie Bradley Jr. in free-agent limbo with an asking price that remains outside of Boston’s budget, Verdugo is expected to move to center field this season with the Red Sox lacking viable alternatives. The position change might be temporary though with promising prospect Jarren Duran waiting in the wings. A star center fielder can generally command a higher salary than a corner outfielder so the Red Sox might be better off waiting for Duran’s arrival when they can send Verudgo back to right field before they entertain the idea of an extension.

While the team certainly views Verdugo as part of their long-term future, there’s no rush to have him sign an extension since he isn’t eligible for free agency until 2025. Verdugo will be eligible for arbitration for the first time next year and that opportunity to see a bump in salary is when extension talks would make more sense.

BOSTON, MA – SEPTEMBER 19: Rafael Devers #11 of the Boston Red Sox reacts before a game against the New York Yankees on September 19, 2020 at Fenway Park in Boston, Massachusetts. The 2020 season had been postponed since March due to the COVID-19 pandemic. (Photo by Billie Weiss/Boston Red Sox/Getty Images)
BOSTON, MA – SEPTEMBER 19: Rafael Devers #11 of the Boston Red Sox reacts before a game against the New York Yankees on September 19, 2020 at Fenway Park in Boston, Massachusetts. The 2020 season had been postponed since March due to the COVID-19 pandemic. (Photo by Billie Weiss/Boston Red Sox/Getty Images) /

Red Sox extension candidate – Rafael Devers

Rafael Devers had a breakout year in 2019 when he hit .311 with a .916 OPS, 32 home runs and a league-leading 54 doubles. If the Red Sox are confident that he will continue to be an extra-base hitting machine, an extension could make sense.

The regression we saw from Devers last year should give the team some pause though. His production at the plate fell across the board with a .263/.310/.483 batting line. Devers still managed to pile up 28 extra-base hits in only 57 games but he struggled to get on base with his walk and strikeout rates trending in the wrong direction.

The Red Sox are expecting a bounce-back year from the young third baseman and they undoubtedly consider him a part of their core. He still has two more years of arbitration before he reaches free agency so there’s no urgency yet but this is around the time that teams start to consider an extension for their top talent.

However, Devers would be foolish to agree to an extension on the heels of a disappointing season. The sides had difficulty in negotiating his arbitration salary with the dispute nearly going before a panel before Devers eventually settled for a $4.58 million salary that’s well short of what he was projected for. If this is his current value, Devers would be wise to bet on himself to regain his 2019 form ahead of any extension talks.

The Red Sox should also be cautious about rushing into an extension with Devers. They shouldn’t worry about his bat but his glove is another story. Defense has always been an issue for Devers, who piles up errors at an alarming rate. Boston has little choice but to send him back out to the hot corner with J.D. Martinez holding down the designated hitter role. What happens in a year or two if Martinez leaves?

Top prospect Triston Casas could be knocking on the door to his major league debut by then, creating a logjam of corner infielders with Devers and Bobby Dalbec. With Devers being the weak link defensively, moving him to DH could be the solution.

Even with the expectation that the National League will permanently adapt the DH in the near future to expand the market, players who provide no defensive value aren’t going to get paid as much. Boston might believe they are getting a team-friendly deal if they extend Devers at his current market value but he could end up being overpaid if he eventually becomes a full-time DH.

There’s risk for both sides in extending Devers this spring. While there might be a middle ground that appeases everyone, it will be difficult to find considering all the uncertainty. This is a case where they should certainly have the discussion but neither side can be criticized if they ultimately decide to wait.

Mar 11, 2020; Port Charlotte, Florida, USA; Boston Red Sox starting pitcher Eduardo Rodriguez (57) walks back to the dugout at the end of the fourth inning against the Tampa Bay Rays at Charlotte Sports Park. Mandatory Credit: Kim Klement-USA TODAY Sports
Mar 11, 2020; Port Charlotte, Florida, USA; Boston Red Sox starting pitcher Eduardo Rodriguez (57) walks back to the dugout at the end of the fourth inning against the Tampa Bay Rays at Charlotte Sports Park. Mandatory Credit: Kim Klement-USA TODAY Sports /

Red Sox extension candidate – Eduardo Rodriguez

Eduardo Rodriguez emerged as the leader of an injury-plagued Red Sox rotation in 2019. The lefty won 19 games while producing a 3.81 ERA and 9.4 K/9 to finish sixth on the AL Cy Young ballot.

Instead of building on his career year, Rodriguez was forced to sit out the entire 2020 season while recovering from myocarditis, a serious heart condition caused by his battle with COVID-19.

Rodriguez has deemed himself 100 percent healthy and arrived in camp this week ready to get his career back on track. The Red Sox will understandably want to see how he looks on the mound during a game before they are ready to endorse his optimism but a strong spring training could motivate them to approach E-Rod about an extension.

Rodriguez is entering his final season before free agency. If they are going to offer him an extension, now is the time. Boston has a long history of struggling to develop pitchers so they can’t allow one as talented as Rodriguez to get away.

There’s always risk when discussing long-term extensions and Rodriguez is no exception. He was fantastic in 2019 but even if we set aside the concerns with missing last season, Rodriguez doesn’t have the best track record of staying on the mound. Prior to 2019, he never made more than 24 starts or threw more than 137 1/3 innings in a season.

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The free-agent market has been brutal for many players outside of the elite class, which might make Rodriguez hesitant to test the market himself next winter. He hasn’t given any indication that he wants to leave Boston so with time running out to prevent him from considering other suitors, Bloom needs to find out what it will take to keep him here.

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