Welcome to extension season.

If late Fall is free agency season and Winter is hot stove season, then early Spring is extension season. As the arbitration process comes to an end and rosters have for the most part taken shape, GM’s and agents begin to focus on retaining their top young talent. Already since the beginning of the new year, GM’s around the league have handed out long-term deals to Clayton Kershaw, Freddie Freeman, Michael Brantley, Julio Teheran, Craig Kimbrel, Homer Bailey, Andrelton Simmons, and Brett Gardner. It’s also been rumored that Mike Trout and the Angels are discussing a deal, which reportedly could end up somewhere in the realm of 6 years, $150 million.

For Padres fans, there are a few players who could be looking at possible extensions, but thus far the team hasn’t handed out any of that sweet long-term scrilla. There’s of course Chase Headley, who is entering his final season of team control, and who has been an extension candidate since before Osama Bin Laden died. There are also a few other guys who could possibly be extension candidates, including but not limited to Jedd Gyorko, Andrew Cashner, and Everth Cabrera. No, not Yonder Alonso.

The questions GM’s, agents, players, and us over-enthusiastic fans all have to answer are who should be extended, who shouldn’t, and what should those extensions look like? For a player like Mike Trout, who could probably get a record breaking 10-12 year deal if he wanted to, it might make more since to seek a 4-6 year deal like the one being rumored. At just 22 years old, Trout could lock himself into one of the biggest contracts in baseball while still hitting free agency in his 20’s and in the prime of his already amazing career. Maybe he could get a 10 year, $300 million deal right now, and that’d be amazing, but if he is who we think he is and salary inflation continues as we think it should, in 6 years he could still get a 10 year deal, and it could be worth $350-400 million, which would give him career earnings of over $500 million dollars. Not bad work if you can get it.

For other players, you take as many years as you can get. Julio Teheran got 6 years from the Braves. Freddie Freeman got 8 years and a whopping $135 million from the very same Braves. Teheran had a solid rookie season and a top prospect pedigree, but that’s it. It makes sense for the Braves to lock him up through at least one free agent season, but it also makes sense for Teheran to get as much security as he possibly can. There was so much range in what could have happened in his next 5 team-controlled seasons. It makes a lot of sense to get what he can now before he ends up with a Tommy John surgery that doesn’t take. For Freeman, with 3 seasons under his belt but only one breakout year, how he convinced the Braves to give him $17 million a year for 8 years without any of those being team options is beyond me. But good for him.

What Freddie Freeman really has going for him, and what most of these players being extended have going for them, is youth. Freeman is 24 years old. He’ll be 32 when he hits free agency. The Braves are betting on production, but if they get anywhere near the production they’re expecting, the contract will be fine, because what they don’t have to worry about is age, decline, and paying a premium for past performance.

The same goes for Teheran (23), Kershaw (25), Brantley (26), Simmons (24), Kimbrel (25), Bailey (27), and even Gardner (30). Every single one of these contracts will end before the player enters his age 35 season. This, I think, is the key takeaway from extension season so far, as GM’s are betting on youth and making sure not to commit long-term dollars when players will be on the downward slide of their career bell curves.

A player who could potentially break that trend is Chase Headley, and it’s likely one of the reasons he won’t be extended. As Chase limps into his age 30 season with a calf strain following offseason meniscus surgery, his extension strategy has to be to get as many years from the Padres as possible; at least 6 but ideally 7 or 8 if he can. The Padres’ extension strategy, which makes sense based on the league-wide trend, should be to try to get Chase to sign a 4-5 year deal. Whether the Padres and Chase are far apart on average annual value or not, there is likely to be a significant difference of opinion on contract length.

Of course, what the Padres could have done is signed Chase to a 4 year deal before his 2012 breakout season, paid him a fairly small sum, and they could have let him walk when he was 32 and his prime years were for the most part behind him. Or after the 2012 breakout season, even at the higher price tag. Regrets, Josh Byrnes has a few. They could also give in and sign Chase to a deal that breaks the current trend. Even if it’s not perfect process, it’d prove this ownership group is serious about retaining top talent, and would be a make up call for not getting a deal done earlier when it could have been more advantageous to them.

Whether or not to extend Jedd Gyorko is different. Entering his age 25 season with only one season of service time, the Padres could give Gyorko a 7 year deal, lock him up through 2 of his free agent years, and not have to worry about what will likely be a fairly steep decline for a player of Gyorko’s build. Why haven’t they done it yet, you ask? They could be waiting to see if what Jedd flashed in 2013 is real. Can he raise his OBP, either by getting more hits, more walks, or a combination of both? Is he really a 20+ home run hitter? Is he a 3-5 fWAR player, or is he a 1.5-2.5 fWAR player? Waiting until the All-Star break to get a bigger sample size isn’t going to hurt much. That said, doing it now isn’t a bad idea either, but we have to remember that given his lack of service time and that he was never more than a borderline top 50 prospect, he doesn’t have the pedigree of some of the other extension candidates from around the league.

Andrew Cashner and Everth Cabrera are remarkably similar extension candidates. Both are 27. Both will have 2 years of team control remaining after the 2014 season. Both are coming off breakout seasons. Both will be making just less than $2.5 million through arbitration this season. Both have premium skills. Cashner carries some injury risk and Cabrera is coming off a 50 game suspension for PED use stemming from a 2012 (important note: not 2013) connection to Biogenesis, but if the Padres can convince either or both to take a 4-5 year extension, I think they should go for it.

Perhaps the Padres are a little bit gun shy. The extensions Josh Byrnes handed out to Cameron Maybin and Cory Luebke just after taking charge as GM haven’t worked out so well. Injuries have ruined both deals to this point, and the Luebke deal seems like a lost cause now. But both deals were made with good process in mind, in keeping with the current extension trends, and neither broke the bank. You can’t always protect for injury, and it would be foolish for the team to avoid long-term deals on the basis of injury fear, especially when they continually bring in veteran players who have known persistent injuries.

Most importantly, as you look around the league and watch these young stars get extended, what you see is the importance of drafting and developing your own talent, and getting them into the big leagues as quickly as their talent allows. All the extended players mentioned earlier, with the exception of Michael Brantley, were drafted by the teams that extended them. You can’t have extension worthy talent if you don’t draft and develop top prospects, and successfully convert them into quality major league contributors.

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  • Lifetime extension for Amarista, because Padres.

  • Billy Lybarger

    Good stuff here Nate. Extending Cabrera is a bit tricky because of the suspension. Everth was on his way to a breakout season, but would his season fade as the second half played on? There is evidence this was possible as he had faded in the second half of previous seasons. I think the Padres can let this full year play out and then see where he is. Jace Peterson should be in AA ball this year, so at least organizationally, the successor is somewhat established. This is not necessarily the case for Headley, where just one season ago the Padres claimed they were in no hurry to extend him, what with a glut of potential 3Bers in the system. A year later the glut is gone, and the Padres have no solution other than to move Gyorko and promote weak hitting Cory Spangenberg.

  • Good thorough review of the young players who were locked up this winter/spring, Nate.

    IMO- I would prefer the Padres recognize they blew it with Chase in 2012 but that they not compound the problem by overpaying for him now in an effort to increase good will with fans. Learn from the mistake and get the next crop of young guys extended to team friendly deals (Cab, Cash, Gyork).

    • Nathan Veale

      I don’t think they’d be making a mistake by signing Chase past the age 35 line in the sand. It’s just the decision to pay market rate rather than getting a discount. The Padres, of course, don’t do long-term deals at market rate, because they are barely a major league franchise.

      • Right. I like Chase until age 35. I dislike that the Padres BLEW it and didn’t get a deal done 2 years ago.

        Even if the Padres felt like they had a glut of third basemen in the system a few years back, they still could have signed Chase to a deal which would have been below market by 2014 standards and then they could have traded him with ease because his contract would have been so attractive.