Clayton Kershaw, Los Angeles Dodgers
Signing franchise pitchers to long-term deals is the hot new thing in the baseball world. King Felix got the ball rolling with his seven year/$175M deal, then Verlander added five more years and $140M more to push his total package over $180M. Clayton Kershaw is younger than both and he has the best ERA in the game over the past five seasons as well. Whispers around the baseball world have the Dodgers left becoming the first player to break the $200M mark. The Dodgers can almost certainly afford to make that kind of commitment to their 25-year-old ace and they want to move on deal during the season, before Kershaw has the chance to shatter arbitration-award records this winter.
Robinson
Cano, New York Yankees
With Scott Boras at the helm, Cano’s ship was plotting a course for free agency and a possible bidding war between the Yankees and Dodgers. However, since Cano dropped Boras to join CAA’s new Jay-Z-led division, the chances that the All-Star second baseman will work out a deal with the Yankees have increased exponentially. Since 2008, Cano has been the most valuable player on the Yankees (by fWAR). If the Yankees get the chance to keep him off the open market, they will probably take it regardless of the cost.
Dustin Pedroia, Boston Red Sox
Dustin Pedroia is the face of the Boston Red Sox, one the top second basemen in the game, and thanks to the team-friendly deal he signed prior to the 2009 season, he is also one of the game’s biggest values. He is signed through 2014 with a club option for 2015 that is almost certain to be exercised barring a dramatic drop in his production, so Boston is not under the same level of pressure with Pedroia as the Yankees are with Cano. Still, Boston may want to move quickly and lock up their star second baseman before Robinson Cano gets his big payday. The two have been very close in value over their careers with Pedroia getting a slight edge in Fangraph’s WAR system and Cano edging him out by Baseball-Reference’s WAR system. Pedroia lacks Cano’s power but he has the superior on-base skills and his glove is arguably the best in the game. He wants to remain with Boston but even so, with Cano set to remake the market, this may be the last chance for the Red Sox to extend Pedroia without paying top dollar.
Matt Wieters, Baltimore Orioles
Matt Wieters didn’t quite live up to the early hype that surrounded him as he approach the majors. The man who had been billed as "Joe Mauer with Power" hit a decent, if disappointing .288/.340/.412 in his rookie season in 2009 and slumped to a .249/.319/.377 line the next year. However, Wieters has started to find the power half of that equation over the last two years, topping twenty home runs in both 2011 and 2012. Add to that one of the best arms in game and strong receiving skills and you have a player with tremendous value. The Orioles are still a very young team and even after a 93-win season in 2012, the team is looking forward to a bright future. As a result, the 26-year-old Wieters is tops on their list of extension candidates now that Adam Jones is locked up. The biggest barrier to this deal, however, may be his agent. Wieters is represented by Scott Boras and Boras rarely advises his clients to allow teams to buy out free agent years. Even so, Baltimore would love to keep Wieters around past 2016, when he is scheduled to become a free agent.
Matt
Harvey, New York Mets
The Mets have put a great deal of their faith in Matt Harvey and Zack Wheeler. The team refused to include both young arms in any trade deals this off-season and missed out on several big-name players as result, including Justin Upton. Harvey has been everything the team could have hoped in his 73 ⅓ big league innings. In twelve career starts, he has a 2.33 ERA and a 10.9 K/9 rate. He won’t hit arbitration until 2016 and it will seven seasons before he can be reach free agency, but the Mets would do well to lock him in a to deal now cover some or all of that time. GM Sandy Alderson has shown a willingness to make this kind of move, signing Jon Niese to a five year/$25M deal prior to his first-arbitration year.
Harvey looks like one of the top young arms in the game right now and lock him up at a below-market cost would help the Mets free up more money to add talent around him as he and Wheeler come into their own. So far, there doesn't appear to be talks taking place and Harvey is another Boras client, so this may not happen. Still, if Harvey continues at his current pace, the chance to lock him up at a discount will be gone by this October.
Austin Jackson, Detroit Tigers
With so much of fan’s attention focused on Miguel Cabrera’s Triple-Crown season last year, Austin Jackson’s breakout was more than a little overshadowed. Jackson hit .300/.377/.479 in 2012 and while his .371 batting average on balls in play (BABIP) may not be sustainable, his walk rate improved to 10.9% and he got his strikeout rate under control to some degree as well. His glove has always been regarded as well-above average and he a strong base runner as well. He will make $3.5M in this, his first arbitration-eligible season, but the Tigers would probably like to keep him around past 2016, when is currently scheduled to become a free agent. Reaching an agreement this year could save the Tigers a good deal of cash, especially if he looks on track to match his 2012 performance at the plate.
Desmond Jennings,
Tampa Bay Rays
The Rays are the masters of the early-career extension. Both Evan Longoria and Matt Moore signed long-term deals with less a full season of time at the major league level. While
TampaBay has become one the top organizations for developing pitchers, they have had less luck on positional player side. Adding Wil Myers helped brighten the future outlook in the outfield a great deal. Locking down Desmond Jennings would be a good step two. Like the Tigers Austin Jackson, Jennings is an excellent defender and a strong base runner with a bat that has started to show promise. He hit .246/.314/.388 last year in his first full season, but his track record promises a reduction in strikeouts and strong walk rates as he adapts to playing at the highest level. For all their positional versatility, the Rays have few serious options now in center and no one close to the majors who will rival Jennings for the position in the near future. He is still a full season away from arbitration and he won’t hit the free agent market until 2018, but for the low-budget Rays, even a few years of strong arbitration raises would be a significant burden.
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