We all know the debate. The reward of signing that super-prospect long term early in their careers versus the risk of said prospect becoming Lastings Milledge. We all want an Evan Longoria on our team, but no one wants to know that the reason their team can’t sign the left-handed reliever they desperately need is because of the AAAA 3B they released two years ago. The question is, who in baseball right now deserves an extension, how much and for how many years would the extension be for, and should the team or player actually sign. In this segment we’ll go division-by-division taking a look at your favorite players. Frankly, you won’t see any relief pitchers on this list because history has told us that for every reliever who pitches 1000 innings in their career, there are 1000 other pitchers who won’t throw 200 good innings. In fact, since 1980 only 43 relievers have thrown 1000 innings and only one of them, Trevor Hoffman, was able to strike out over a batter per inning over that time.


Arizona Diamondbacks – The Diamondbacks have a few players I think they should explore extensions with. Among them, Patrick Corbin, Wade Miley, Ian Kennedy, Trevors Cahill and Bauer, Tyler Skaggs, Daniel Hudson and Paul Goldschmidt. Kennedy and Bauer seem unlikely, since both are Scott Boras clients. Miley is the most interesting, fresh off a rookie campaign in which he was one of the best pitchers in the league, compares nicely to Ubaldo Jimenez. In 2009, Jimenez signed his $15.75 million, five year contract at age 25 after his first full season. Miley is also 25, and his peripherals shouldn’t give the Diamondbacks too much pause. He should be able to get a contract in the five year, $18 million area, which I think would be palatable for both Miley, his agents, and the Diamondbacks.


Colorado Rockies – The Rockies have already locked up their second best prospect of all time first to a seven year, $45 million deal, then a six year, $118 million extension after year four of the first contract. But, handing out these contracts is a little bit easier when you’re giving them to Troy Tulowitzki after a 24 home run, 99 RBI rookie season. It’s a little bit harder when your team’s best candidate for an early extension is Dexter Fowler (represented by Scott Boras), and the most likely player to sign a team-friendly deal is Wilin Rosario. Drew Pomeranz isn’t the type of pitcher who will thrive as a long-term Rockie, Alex White and Jhoulys Chacin walk too many batters without striking enough batters out to balance out the free passes, and Josh Rutledge hasn’t shown enough patience to suggest he won’t be exploited by Major League pitchers. In order for the team to get any value out of an extension with any of these players, the contracts would have to be so low that it wouldn’t make sense for the player to sign. The risk of each of these players not being even major league average players is high enough that I actually think the Rockies would be best served seeking trades involving these young players for proven players. As far as Rosario, very few catchers sign extensions early. Even the Twins waited until Joe Mauer was about to hit free agency to give him his contract. Yadier Molina’s four year, $15.5 million with a one year $7 million club option (which was eventually exercised) contract could be a comparable, but that deal was signed after Molina’s third MLB season. Given that Molina was a defensive specialist with his first good offensive season, and Rosario had a great offensive rookie season without the defensive reputation to follow, I feel Rosario should be able to demand the same contract Molina received over the same years in which Molina received it. Since Molina’s deal covered his arbitration years and two free agent years, Rosario’s contract would have to cover his pre-arbitration years as well. At $1 million per year and factoring inflation of contracts since 2008, Rosario and the Rockies should both be happy with a seven year, $22 million contract.


Los Angeles Dodgers – Between Yasiel Puig already being signed long term, and the midseason trades that sent Nathan Eovaldi and Rubby De La Rosa to the East Coast, there is a striking dearth of players in the early part of their careers. One could argue AJ Ellis is worth a three year extension, and you won’t get any argument here, but it’s not really what i’m looking for with this article. Fortunately, the lone long term extension-sensible player in Los Angeles is a little-known left-handed pitcher named Clayton Kershaw.  The Dodgers might feel the scar of Frank McCourt for at least the length of Clayton Kershaw’s career. Having missed their opportunity to sign Kershaw to a deal even remotely team-friendly, he’s now two years away from becoming the wealthiest pitcher in MLB history. Already signed for his second-to-last last pre-free agency season at $11 million,  we can’t even really use the situations of Justin Verlander and Felix Hernadez anymore. We can assume Kershaw beats Lincecum’s $22 million salary for his last pre-free agent year. Cole Hamels ($24.4mil AAV) and CC Sabathia ($24.4mil AAV) are the two highest paid starting pitchers, and Kershaw has every right to make more than each of them. With Kershaw being only 26 years old at the time he hits free agency, we could see a record. If Kershaw signs this offseason to a deal that supersedes his 2013 contract, I could see a seven year, $168 million contract. If his extension begins with the 2014 season, it could push to $200 million from 2014 to 2021.

I’m still catching my breath from the thought of a $200 million pitcher.


San Diego Padres – The Padres are in a similar state of ownership flux as the Dodgers without the high-priced long term contracts glutting up every position. Rather, they have several young major leaguers who fit San Diego well.  Logan Forsythe is a 25 year old second baseman who shows all the signs of being a solid second base option for the low budget Padres who might be worth locking up at a discount. Yasmani Grandal probably can’t be extended due to his recent suspension, as giving an immediate reward for cheating would be poor organizational branding. Yonder Alonso still isn’t showing the power that his swing suggests is there, and I’m starting to wonder if he’s James Loney incarnate. They could lock him up long term, but it would shouldn’t be more than a four year deal with two club options. However, the Padres have potentially the best third baseman in the National League in 28 year old Chase Headley. Only two years remaining until free agency, Headley is probably looking at a $7 million contract for 2013 and a $14 million salary for 2014 if he has another great year. Much like Kershaw, Headley is well within his rights to expect near-market salaries for any free agent years included within his contract. The problem then becomes the Padres’ typically low budget. If I’m Headley, I want a six year, $84 million contract, buying out four free agency years at $16 million each. If I’m the Padres, I’m not sure I’m prepared to give 40 percent of my budget to one player. The Padres probably only have the ability to buy out one free agent year, which should be totally unacceptable to Headley and his agent. Best case scenario for everyone involved might be to trade Headley this offseason, or wait one more year to make a playoff run then look to trade him with one more year of arbitration left before free agency.


San Francisco Giants – The Giants have had the best run of first round draft picks in recent memory. Since 2002, the Giants have taken Matt Cain, Tim Lincecum and Madison Bumgarner in the first round and locked them up to at least multi-year deals. Cain signed four and three year deals leading up to his six year megadeal this season. Lincecum has never signed for more than two years, instead betting on his past performance (and losing, maybe. Hard to call a 28 year old who has made $65 million or so a “loser”). Bumgarner was just signed to a five year extension with two club options this season that figures to make him the contractual envy of Major League Baseball by the end of it. It’s time for recent National League Most Valuable Player and fellow Giants First Round draft pick Buster Posey to join the ranks of the contractually extended. The Giants’ best chance to extend Posey was last year after he broke his leg, but the risk there is obviously so great it doesn’t make a lot of sense for the team. Posey is arbitration-eligible for the first of four years this offseason. MLB Trade Rumors has an extensive article on Posey’s extension outlook. MLBTR suggests Posey seek a five year, $47 million contract that buys out one free agent year for $17 million. They also suggest his agent could seek two additional years for $17 million and $20 million each, bringing the total to seven year, $84 million. The issue I have with giving early career extensions to catchers is the obvious wear-and-tear their bodies take. I think a fair solution would be to take the five year $47 million deal and add the two seasons on the end of it as a two year, $37 million mutual option. That way, if the Giants feel confident in the then-31 year old Posey’s health and ability to produce offensively, they have the option to pick up the contract and Posey gets what he originally wanted. If not, the two part ways.