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Who will the Red Sox sign to an extension next?

The Red Sox have a history of signing some of their young players to contract extensions. Following the signing of Wade Miley, who could Ben Cherington potentially pursue next?

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As we head into a new season, some members of the Red Sox 25-man roster find themselves in contract limbo. Contract extensions, in general, tend to favor the team. With no open-market competition, the players have less negotiation leverage and are usually unable to maximize their value if they hope to sign an extension. Players, however, have their reasons to sign extensions: some particularly enjoy playing for a certain team while others value the security of signing a long-term deal with guaranteed money.

The Red Sox have a considerable amount coming off the books after 2015 with the pending free agency of Mike Napoli, Shane Victorino, Rick Porcello, Justin Masterson, Edward Mujica, and Craig Breslow all scheduled for free agency. Here are a few players that Ben Cherington and company could consider giving money and security to before the open market is reached.

Joe Kelly

While Kelly is scheduled to hit free agency after the 2018 season, the Red Sox did just sign Wade Miley to a three-year extension with an option for a fourth year to buy out arbitration and at least one free agent year. The team does have a history of signing pitchers to buy out arbitration and early free agent years, having done just that with Jon Lester in 2009 (five years, $30 million) and Clay Buchholz in 2011 (four years, $29.945 million).

Kelly came over to the Red Sox as a pitcher, similar to Porcello, presumably not yet a completely polished product. Kelly will start the 2015 season as a 26-year-old hurler who has not yet completed a full season as a starter. If the Red Sox think they can get good value out of Kelly by signing the Anaheim, CA native to an extension, expect Cherington to go ahead and get a deal done. The fact it's unclear exactly who Kelly is as a full-time starter might make this a task for next year, though.

Mookie Betts and Xander Bogaerts

So I'm going to put this in the Mike Trout contract extension-type territory (although I'm in no way saying that either player is anywhere near Trout's level of play or pay). If one of these two players breaks out, it would be financially prudent (long term) for the team to attempt to lock up them up to a lengthy contract.

If Betts or Bogaerts hits their ceilings, they are franchise cornerstones, and inflation will only continue to raise the price tag on players on the open market. A $20-million player is no longer what it was just five years ago, and there are more of them every year.

One potential hiccup here is that Bogaerts' agent is Scott Boras. Boras, historically speaking, does not let his players sign extensions (although Jered Weaver is a relatively recent exception). Betts recently left Jody Gerut at Wasserman Media Group for Relativity Spots, the same agency as fellow Red Sox player David Ortiz, and would likely be more receptive to a potential extension.

Rick Porcello

This is the obvious one. Porcello, acquired in the offseason trade for Yoenis Cespedes, will be just 26 years old on Opening Day. He's an incredibly talented pitcher who just recently seems to have tapped into his potential. Porcello, however, has been plagued with inconsistency throughout his career -- not all of it his doing -- and the Red Sox will likely have to wait to see what they have with the righty before attempting to lock him up with any significant investment.

Despite having not yet thrown a pitch for the Red Sox, Porcello is already facing questions on his future with the organization. The righty is not ready to discuss his contract situation.

"I just got here and met the guys last night so I think it's premature for that," Porcello said to the media in January. "I'm just trying to settle in and fit in with everybody, get to know the staff and the guys."

Porcello is coming off a season in which he posted a 3.43 ERA. As Pablo Sandoval proved this offseason, hitting the open market during the prime years of your career alongside a track record of success practically guarantees a player a payday. So long as Porcello doesn't suddenly fall apart like Justin Masterson did a year ago, he'll be happy he bet on himself.

"It's always strange, at least for me, because growing up you play baseball because you love playing the sport," Porcello said in January. "And then the money start gets thrown around and obviously for somebody, from a personal financial standpoint, that's a big opportunity and big thing to look at. But for me, over the course of my career, no matter how much money I've made I'm not happy unless I'm playing well."

Porcello projects as around a 3-3.5 WAR pitcher through his prime (unless he makes a significant jump and puts everything together). On the open market, this type of production would garner around $15-17M annually. Given that Porcello will be 27 years old when he hits free agency, he could sign a five year deal and hit the market again at 32 years old, when he could get a deal similar to the contract James Shields signed with the Padres (taking inflation over the course of Porcello's next deal into account). Unless Porcello implodes this season, he'll be taking a big check to the bank at some point in the next year. Whether it's with the Red Sox or some other team remains to be seen, but he very well could be the next extension for Boston.