Poll: Who Will Sign An Extension This May?

Let's start the weekend up with a poll. As MLBTR's Steve Adams noted recently, two young stars (Adam Jones and Miguel Montero) signed significant extensions during May of 2012. While there have not been significant rumblings about any similar deals recently, the Jones and Montero deals both sprung up with relatively little advance buzz: Jones said he was not aware of any talks with the Orioles just a month before his six-year, $85.5MM deal was inked. And the build up to Montero's five-year, $60MM extension consisted largely of the Diamondbacks' acknowledgement that the team was open to in-season negotiations.

Jones had one year of arbitration eligibility remaining when he signed, while Montero would have become a free agent at the end of the year. Both were relatively young (26 and 28, respectively) and fairly well established as above-average players at premium defensive positions. And each had been with their teams for all or virtually all of their big league careers.

With those deals in mind, let's take a look at some generally comparable position players who could be positioned for similar deals. We will not include Robinson Cano, as he is at a different level of performance and contract extension, along with being somewhat older. Anyhow, we already asked MLBTR readers what they think about the likelihood of a Cano extension. Likewise, we'll leave out Chase Headley, given his recent comments. (Also, MLBTR readers just weighed in on a possible Headley extension, with the majority believing a trade was more likely than an extension.) 

The Nationals' Ian Desmond, 27, has continued to build off of his emergence last year. He sports a .296/.311/.530 line, although he has also registered seven early errors. The shortstop has spent his entire career in the former-Expos organization, and is poised to hit the open market in 2016. We know the Nats are open to negotiating an extension with Desmond, and the Elvis Andrus signing provides a relevant (albeit imperfect) point of reference. 

Orioles' catcher Matt Wieters is another obvious candidate. He will turn 27 later this month, and is looking at free agency in 2016. Ongoing negotiations between Wieters and the O's are seemingly at a simmer, but could pick up at any time. While Wieters is off to a bit of a slow start, slashing just .224/.297/.388 to date, he also probably had less to prove this season than Desmond.

Jacoby Ellsbury of the Red Sox, 29, is similarly situated to Montero. He has played his entire career in Boston, but is set to become a free agent after the season. While the center fielder has not returned to his MVP-level 2011 season, when he exploded for 32 home runs, he has bounced back from his injury-shortened 2012. Thus far, his batting line (.286/.338/.405) and league-leading steal totals (11) are right in line with his strong 2008-2009 seasons. While both player and team appear interested in discussing an extension, Ellsbury's representation by Scott Boras — and the possibility that he could significantly raise his value with an injury-free 2013 — could make a deal unlikely.

Jason Heyward of the Braves is two years from free agency at just 23 years old, but as MLBTR's Tim Dierkes notes, the cost-conscious Braves could look to extend him. Heyward is currently on the DL after undergoing an appendectomy, and has had a poor start to the year. Nevertheless, he has established himself as few big leaguers have at his age. 

Austin Jackson, the Tigers' center fielder, is a young 26 and still two years from free agency. He is also a client of Scott Boras. But his strong early track record could make him a target for Detroit to try and lock up early. With so many big-money free agent deals on the books, it could make sense for the Tigers to try and save on Jackson by guaranteeing him money in advance. Jackson is off to another good start, putting up a .293/.356/.407 line to go with five steals.