Boston Red Sox: Odds of Each Extension Candidate Getting New Contract

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Boston Red Sox: Odds of Each Extension Candidate Getting New Contract
Bob DeChiara-USA TODAY Sports
Jon Lester is certainly a candidate for an early extension.

The Boston Red Sox don’t usually do extensions, but with three great candidates set to hit free agency in the near future, it may be time to start.

To be fair, general manager Ben Cherington has been too busy bringing players to Boston to spend time trying to keep those already on the team there longer. Cherington had to find a slew of players to fill the voids created by last season’s club. Negotiating extensions was probably close to the back of his mind.

But with the voids filled through free agency and trades, Cherington now has the time. Here’s a look at the candidates who Boston could look to extend, along with the chances of an extension happening.

 

Jacoby Ellsbury, Outfielder

Jim Rogash/Getty Images
Will Jacoby Ellsbury sign an extension or test the free agency waters?

Jacoby Ellsbury is expected to be one of the biggest available players in next season’s free-agent class, as his contract is set to expire after the 2013 season. That is, unless Boston extends him before that happens.

Ellsbury has been good when healthy, but has had a tough time avoiding wrong-place, wrong-time injuries. In 2011, Ellsbury finished second in the American League MVP Award voting after hitting .321/.376/.552 with 32 home runs and 105 RBI.

This past season, Ellsbury was limited to just 74 after separating his shoulder, and hit .271/.313/.370 with four home runs and 26 RBI. It’s questionable as to whether he has the capability of hitting 20-plus home runs each year, but that won’t stop Boston from trying to keep him past 2013.

Cherington recently spoke to Peter Abraham of The Boston Globe about the chances of extending Ellsbury:

Ellsbury is a very talented player and we know what he can do on the field when he’s feeling good physically, We’re obviously a better team when he’s on the field and we’d love for him to be a Red Sox for a long time. But I’m not going to get into anything other than that. We’ve had a good relationship with Jacoby and hope that continues.

Although it would be smart of Boston to talk to Ellsbury about a new deal, it seems that he’s much more comfortable testing the market first and seeing what’s out there. If Ellsbury is going to be a Red Sox past this upcoming season, it will be because he re-signs in the offseason and not because he signed an early extension.

Odds of an Extension: 10 Percent

 

Jon Lester, Starting Pitcher

Jared Wickerham/Getty Images
Will Jon Lester hit free agency or will Boston lock him up?

After 2013, the Red Sox hold a 2014 team option worth $13 million on Jon Lester. But that shouldn’t be an issue if Boston decides to extend him beforehand.

Lester has pitched atop Boston’s rotation the last couple of seasons with inconsistent success. From 2008 through 2011, Lester went 65-32 in 128 starts with a 3.33 ERA in 813.1 innings of work. But last season, Lester won just nine games in 33 starts, posting a career-high 4.82 ERA in 205.1 innings. It was by far the worst campaign of his seven-year career.

Lester isn’t worried about what’s down the line, though, just what’s in the immediate future, according to Rob Bradford of WEEI. Lester said:

I’m not worried about in four years. I’m worried about this year. This is a big year for me. Not only as far as stability, but also me just getting back to being me. Getting back to the pitcher I know I am. That’s the biggest thing for me.

But in regard to a potential extension, Lester said the Red Sox have not approached him about one, according to Bradford.

It’s certainly an interesting situation. The Red Sox definitely have the money to extend, but will probably wait to see how he bounces back after a tough year. Despite Boston bringing in Ryan Dempster this offseason, Lester is still expected to be the starter on Opening Day.

If Lester pitches well through the first big chunk of the season—let’s say past the All-Star break—then I could foresee talks start to pick up. If Lester continues to pitch poorly, I’d expect Boston to exercise his option for 2014 and see how he does then before thinking about keeping him past then.

Odds of an Extension: 35 Percent

 

 

Dustin Pedroia, Second Baseman

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Dustin Pedroia certainly has a good chance of signing an extension with the Red Sox.

When it comes to Dustin Pedroia, it seems that the Red Sox aren’t quite certain on whether they want to extend him or not.

Back in mid-November, Joe McDonald of ESPN Boston reported that Boston was planning on talking about a new contract with Pedroia this winter. But to this point in the offseason, nothing has happened—or at least nothing has been brought to the attention of the media.

Pedroia is owed $10 million in each of the next two seasons and the Red Sox hold a team option worth $11 million for 2015. Bradford reported a few days ago that negotiations are expected to begin with Pedroia sometime this spring, but Cherington’s comments about extensions don’t seem too convincing:

I can’t rule it out, but I can’t rule it in, either. It’s something that, I think in those cases, certainly the closer a player is to free agency, the more likely those conversations take place. For the team, there’s obviously a benefit to having players on a good contract and having control left.

So, there’s a fair amount of incentive for the team to just let that play out. When you have players who have done a lot for the team and mean a lot to the team, I think you always have to have an open door to a conversation, but that doesn’t mean that it goes anywhere. And there’s nothing going on right now as I sit here today.

Pedroia is absolutely the type of player that Cherington mentioned; someone who has done a lot for the team and means a lot to the team. The undersized second baseman has been one of Boston’s best players since 2007, his first full season with the Red Sox. He’s been a mainstay in the heart of the team’s lineup and is expected to stay there for a long time.

Odds of an Extension: 60 Percent

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