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Friars Need to Be Smart and Trade Headley This Winter 

Chase Headley

Should the Friars try to extend 3B Chase Headley or trade him? And if they decide the best course would be to move him, when does the club do that, this winter or ahead of the trade deadline? These questions have been asked and written about multiple times, both here and everywhere, with opinions ranging from one side of the spectrum to the other. Yet I can’t help but think the Padres are going to make a big mistake when it comes to Headley.

A recent report from Joel Sherman of the New York Post indicates the Padres are leaning toward keeping their All Star 3B rather than trading him. Whether that means they both have an idea of what it will take to extend him and are willing to meet that price is not known. Of course Sherman goes on to say that the Friars will listen on him this offseason but that’s standard operating procedure and should be the case for any player in the organization.

I’ve thought long and hard on the subject and as much as I might like Headley and have spoken out often in the past of the importance of retaining key homegrown players, I’ve come to the inescapable conclusion that the Padres would be best served dealing him this winter.

For the sake of argument, let’s assume the team and player can come to an accord on a new, long term contract. That deal would likely be something in the neighborhood of five years, maybe six, and run anywhere between $75MM and $100MM (for an AAV of between $15MM and $16.67MM).

For those of you who think that may be high, realize Ryan Zimmerman signed a six-year, $100MM deal with Washington and Headley has been worth a combined 13.1 WAR (according to Fan Graphs) over the last three seasons while the Nationals 3B has accumulated 9.5 WAR during that same stretch. At least in terms of WAR Headley has been the superior player.

So it’s not unfair to expect a long term arrangement between Headley and the Friars to approach the figures I suggested. If we also assume the Padres payroll over the next several seasons will fall in the range of $80MM and $90MM (management says that payroll for this season will be around $80MM), it means that Headley will account for roughly 16% of the team’s total salary commitments in the years ahead.

Headley is a good player, not a great one. He has had one great season and a few good ones. He’s never come close to the power numbers he produced during the 2012 campaign in any other season so it’s more likely he’ll never be that prolific of a power hitter again. His defense is well above average and he brings value on the base paths but if the Padres only have room to pay one guy $15MM or more per season, is Headley the guy you want to build around? I wouldn’t.

So if signing Headley to a fair market extension is not practical that leaves two options: One, trade him or two, let him play the 2014 season out, offer arbitration and take the compensatory draft pick.

Fact is the Padres would be certain to extract more value in trade than they would gain from a single compensatory draft pick. Consequently the smart move would be to move Chase Headley via trade so the only question remaining is when is the optimum time to do it.

If they were to wait until the trade deadline it is possible that they could find a team desperate enough to overpay in order to enhance their postseason chances. But the reality is that fewer trades are made at the trade deadline between what was traditionally known as “buyers” and “sellers.” Last season there were several trades made leading up to the deadline but I found only a couple that saw a team trade a veteran player for prospects. One was Houston sending Bud Norris to the Orioles for L.J. Hoes, Josh Hader and a competitive balance draft pick. The other saw Chicago trading Alfonso Soriano to the Yankees for a minor league pitcher named Cory Black. In essence the days of teams selling off veteran players for premium young talent at the trade deadline are essentially over. Most teams simply value their prospects too much and are unwilling to sacrifice young talent for a rental.

The Friars best opportunity to deal Headley is this winter. For one, more teams may consider themselves contenders today than might in July. That will give the Friars a larger pool of potential trade partners and subsequently the ability to better capitalize on their leverage.

Two, if Headley is traded at the deadline the acquiring team cannot receive a compensatory draft choice if they offer him arbitration after the 2014 season. However, if the Friars were to trade him this winter then compensation would still be attached making him more valuable to the team adding him.

I suppose if the Padres sincerely felt they could compete they could justify hanging onto Headley for now. It would be next to impossible to find similar production at the 3B position through free agency or trade. Yet that doesn’t mean they couldn’t trade him and still improve the roster overall.

The Friars are in an unenviable position with regard to their homegrown 3B. Extending him would probably require a commitment that would hamstring the team’s budget for years to come. Allowing him to leave as a free agent while collecting a compensatory draft choice would be poor asset management. That leaves trading him as the best option but the Friars need to move him now while he has the most value. Keeping him at least until the deadline is a risky proposition and one that could cost the club both in the long and short term. Unfortunately, it appears that is the direction the team is going to take.  

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About the author: Glen Miller

Life-long baseball and Padres fan who attended his first Friar games way back in 1983. I've been a contributor on Friarhood for more than two years and enjoy talking baseball with the knowledgeable fans that frequent the site. Prior to my beginning here I owned and operated my own San Diego sports site while writing for several other sites focusing specifically on hockey. When not watching, reading or writing about sports I might be sleeping or perhaps spending time with my family since I have few other hobbies. I did recently try my hand at golf and am a pretty good pool player to boot.

  • ballybunion

    Is this take-two or take-three of the ‘trade Headley’ topics?

  • SDMainiac

    I’ve been against trading Headley but if the cost is that high, trading him this winter makes sense.