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Chase Headley Contract Discussion

When you have a season like Chase Headley, you play for the Padres and you are just two years away from free agency, there are going to be rumors about contracts and trades. It happened with Adrian Gonzalez and it will happen to someone else in future. In the meantime, let us discuss how Chase got here and what is to come.


Chase Headley is not under contract. He is, as they say, under team control and will likely sign a one year deal for a projected $8.3 million in the next month or so. After that contract runs out, he'll have one more year of team control where the team can sign him to another 1 year contract. When that second season is done, he becomes a free agent. The most valuable Padres player will likely play for another team in 2015 and say Sayonara Sunny San Diego!

This is not a surprise to anyone who follows the business of baseball. And it was something that was carefully considered going back to Headley's midseason call up in 2008. Back then the team wanted to make sure that he didn't accumulate enough service time that season to become a free agent in 2014, which was a possibility if they had promoted him at the start of the season. And they also wanted to try and avoid an accumulation of service time that would result in Super Two status for the 2011 season. They succeeded in the first part, but embarrassingly failed on the second part. Headley was able to get an extra $1.8 million from the Padres in 2011 due to this carelessness. But, anyway, that GM has been sacked and the people responsible for his sacking have been sacked. Moving on.

Now that Chase Headley has finally tapped into his potential, a lot of Padres fans would like to see him stick around a little longer than just the next two seasons. And they certainly do not want another Adrian Gonzalez situation where the team is forced to trade the player for prospects before they lose him for nothing. The best way to have avoided that was (and perhaps still is) to sign him to a contract that buys out one or more of his potential free agent years. But, when could this have been done? And, is it still a possibility?

Looking back, there have been some obstacles to giving Chase a long term contract similar to the ones the Padres have handed out to Cameron Maybin, Nick Hundley and Cory Luebke. Right now, the biggest obstacle is that Headley is coming off a big year. The Padres are a budget conscious team and in theory are not able to pay for a player at the peak of his value. They need Chase to get a little charitable and take a little less in exchange for security. This is not the best bargaining position. In 2011, Chase hit better than he had in a long time, but also got hurt and his home run total hit an all time low. At that point the team and the player probably wanted to wait things out before agreeing to anything. In 2010 the team did well and Headley held his own. The Padres were in no rush to get him signed 4 years before free agency and after a similar so-so 2009 the team was probably questioning his potential. 2009 was a strange time to work out any sort of deal as well since the ownership and GM were changing over. He was also about to switch back to playing 3B again after some awful years in LF. If hindsight is 20-20, the missed opportunity was after 2008. Sure, he'd been playing out of position and didn't have a full season under his belt, but his promise was never higher and his cost would have been a lot less. I don't blame anyone for missing it, especially giving the financial situation of the team, but you wonder what could have been.

Coming back to present day, there is still some wiggle room to get a deal done. Trader Josh Byrnes even hinted at starting some discussions in the Spring. This offseason, we also saw two of MLB's top 3B avoid free agency by agreeing to contract extensions. Evan Longoria of the Tampa Bay Rays signed for 6 years, $100 million on top of the 4 years, $36 million he had already worked out for the next 4 seasons. That's a total of 10 years $136 million. David Wright of the New York Mets was, like Headley, a year away from free agency but with a longer history of being a top player than Chase or Longoria. He signed for 8 years, $138 million. Both of these deals have been referred to as team friendly. These players wanted to stay with their current teams for the long haul.

That brings us back to the question of whether the Padres and their star 3B could work out one of those deals. First off, I'm not convinced that Headley would be looking for a team friendly deal. I'm not 100% sure, but I believe his family is based in Tennessee in the offseason so his roots may not be that strong in San Diego. He doesn't have a hitting coach or something here that he can attribute to his success and I'm sure he's not the biggest fan of the ballpark from a hitting standpoint. These are not reasons to push a player out of town, but they certainly hint at him not looking to leave money on the table in order to stay. That being said, both Wright and Longoria are more accomplished players than Headley and even at a discounted price, the Padres might still be able to get Headley for something in that range.

Longoria's deal is a little ridiculous. For the next four years he'll be average $9 million per year. As mentioned early, Headley is already likely to get $8.3 million this season without having reached free agency, without any All Star appearances, without any seasons where his play helped carry the team to a World Series and really only one season for Chase that was deserving of being paid like a top player. Suffice it to say, the Rays have quite the deal. If you combine his two deals and break out the 5 years from 2015-2019 you get $63 million over than time span. $12.6 million average annual value (AAV) there. I chose those years because Longoria is going to make way too little in 2013-2014. David Wright, however, from 2013-2017 is due $91 million. An $18.2M AAV. Both deals encompass quite a lot of money. More money that Padres have ever paid a player.

However, with TV money increasing and inflation going up every team is going to have to spend more than they ever have at some point. And there's a chance the Padres could crack open a window of contention if they keep Headley around even at those prices. They could certainly tighten up a little elsewhere by letting Edinson Volquez go after 2013. Let Clayton Richard and Huston Street walk after 2014. Perhaps trade one or more of the arbitration eligible players like Luke Gregerson, Joe Thatcher or Will Venable. And get a high level of production from at least a half dozen of the franchise's better prospects while eschewing any free agent acquisition. Then they could make such a deal, keep things mostly intact and not overextend themselves on payroll. Somewhere on the order of 5 years, $80 million might be doable.

On the other hand, other teams have to deal with inflation and will get increased TV money so they might be willing to spend even more than that. Perhaps even a team that plays in a Ravine up north might want to throw dollars at him. If that's the case and that sort of big money isn't enough to keep Chase away from free agency, then I'm not sure that there's anything the Padres can do. Instead, this time next year we'll be discussing which team has a 3B opening and has the prospects to trade for our stud hot corner man.