The next wave of MLB contract extensions

Stephen Dunn

With free agency and arbitration winding down and the trade deadline months away, teams are starting to focus on extensions. Which players and teams should we expect to tie the knot during the next few weeks?

Chances are that if you work for the Atlanta Braves, you've had your contract extended over the last couple of weeks. The Braves have been on an extension kick, locking up Freddie Freeman, Julio Teheran, Craig Kimbrel and Andrelton Simmons, but they're just getting that part of the calendar started. Arbitration is over and nearly all of the free agents have found new homes, so the roster gurus in MLB front offices are starting to think about locking up the talent they already have in the fold. As spring wears on, expect to see a few names coming up again and again in extension conversations.

On this list you won't find names like Mike Trout, Manny Machado, Stephen Strasburg, Chris Davis, Miguel Cabrera or Matt Wieters because those players aren't in a position where an immediate extension is likely or necessary. They are much more likely to wind up signing long-term deals midseason or before 2015. The following players have one year left on their current deals and will likely call off talks if there isn't a deal in place by Opening Day. What they decide over the next six weeks is going to determine how much fun next offseason is going to be.

Hanley Ramirez (SS - Los Angeles Dodgers)

If you cover one eye and look at Hanley Ramirez's career so that 2011 and 2012 are a little blurry, he looks like a superstar. He hasn't been a superlative defender, but he's been good enough to hack it and when you mix "good enough at short" with power, speed, and on-base ability, you're looking at a perennial MVP candidate.

Ramirez was such a player from 2006 to 2010 and that player was reborn in 2013 during his first full season with the Dodgers. Ramirez missed time -- a lot of it -- but still managed an insane 5.1 fWAR in just 86 games. When you see 20 home runs and 10 steals, you don't stop and stare, but the .345/.402/.638 line while playing in the NL West was something to behold. When you adjust for league and park effect, Ramirez's 191 wRC+ means that he was 91 percent better than the league average hitter in 2013. That's Miguel Cabrera territory while playing a decent shortstop at age 29.

It's helpful to Ramirez that he's anchoring the Dodgers' lineup rather than the Marlins' because it means the team that can offer him an extension is a team with endlessly deep pockets. The Dodgers have all kinds of money and are alreadying budgeting $16 million for Ramirez in 2014, which means that any raise will only increase their operating expenses by a couple million dollars.

In projecting Ramirez going forward, you assume plenty of regression in the power department, but you also expect that he'll play more than 86 games in a season. If he's something like a 4.5 win player in 2015 and ages fairly typically, a fair market deal is going to be awfully large and he has plenty of leverage in asking for a market value deal at this point in the calendar. Six years and $20 million a season seems pretty reasonable and the Dodgers have little incentive to wait. If he has a great season, it will cost them far more and if he struggles, he'll still command a hefty price considering what he did in 2013.

Odds of an extension: High

Possible extension: Six years, $120 million

Jon Lester (SP - Boston Red Sox)

It's strange to think that Lester just turned 30 in January considering how long it feels like he's been around. The cancer survivor and no-hitter-thrower has been a consistent and durable starter since making it back to the big leagues for good in 2008. He's thrown 190 innings or more in six straight seasons and despite an evolving strikeout and walk profile, has been a very effective starter in each of those seasons except for 2012, in which he had some likely luck-related problems with the home run ball.

If you aren't terribly worried about those home run problems from 2012, it's easy to see Lester as a three- to four-win pitcher going forward, with the potential to throw in another five- or six-win season for good measure. Lester has been excellent in the postseason and seems well-liked in Boston, meaning that the odds of an extension are even higher, to say nothing of the fact that both sides seem outwardly open to a deal.

The interesting angle here is that the Red Sox may wish to gamble that Lester's value, based on how he finished 2013, will never be higher and that his price can only go down from here. Looking around at peer extensions, Lester is easily in line for $20 million per season on the open market on a deal that spans at least five seasons. The Sox have pitching depth and talent coming from the farm, so the pressure isn't high to get this done.

Odds of an extension: Decent

Possible extension: Six years, $120 million

James Shields (SP - Kansas City Royals)

The Royals don't have the resources to spend like the Dodgers and Red Sox, but they bet the farm on James Shields carrying them back to relevance, and letting him walk after two seasons probably isn't the best way to make sure that happens. If the Royals want to keep Shields around, they're going to need to lock him up before he gets a chance to test the market.

Like Lester, Shields had one bad year in a sea of consistency, but unlike Lester, he tends to throw 220 innings or more in a given season. With Shields you're getting a big time innings-eater who also happens to be quite effective while on the mound. The knock here is that he's older and will be 33 during the 2015 season.

The Royals don't have the kind of financially flexibility that other organizations do, so their strategy here might be to offer Shields a longer deal than you would expect but with a slightly lower average annual value. Shields would probably get four to five years on the market at 33, but if the Royals offered him five or six it might save them something if their yearly budget was in danger of breaking. He's likely looking at something in five-year range between $90 million and $100 million.

Odds of an extension: Decent

Possible extension: Five years, $90 million

Max Scherzer (SP - Detroit Tigers)

Scherzer's case is one of opposing forces. He's a reigning Cy Young winner, beloved by his organization and fan base, and on a team that traded away Doug Fister and Prince Fielder presumably to free up money for the longrun. In that sense, a Scherzer extension looks extremely likely. Yet Scherzer is represented by Scott Boras, improving his game with each passing season, and might find himself alone on the market if Lester and Shields sign long-term deals. After those two, the jump to Masterson as the next best option on the 2015 market is significant. Scherzer is in a prime position to sign an extension, but he's also in prime position to take advantage of the market if he doesn't.

It took Scherzer a while to become the ace that he is, but the improvement in his mechanics over the last year and a half has made all the difference in making the leap from above-average to great. Even if you don't buy him at his 2013 levels, his track record of health and solid performance gives him a nice floor. He's coming off an excellent season, but the Tigers don't have the luxury of waiting for his price to come down. If he doesn't have a deal by March 31, he's going to test the market and the market is going to pay him handsomely as long as his right elbow and shoulder remain intact for another 162 games.

Scherzer will hit the market ahead of his age 30 season, so a six-year deal is probably in his future with an annual salary that's above what we're likely able to comprehend. Clayton Kershaw, Justin Verlander and Felix Hernandez had longer track records than Scherzer when they signed their deals, but they also did so ahead of free agency. If Scherzer gets there, he'll probably rival Kershaw's yearly price. Greinke's six-year, $147 million deal is probably the baseline, but with television revenue on the rise, six years and $180 million isn't out of the question. The Tigers won't extend him at that price, but might be willing to pay him now if he's willing to take a discount.

Odds of an extension: Low

Possible extension: Six years, $160 million

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