Will Latest Alex Rodriguez PED Saga Result in Yankees Trading for Chase Headley?

Zachary D. Rymer@zachrymerMLB Lead WriterFebruary 6, 2013

SAN DIEGO, CA - AUGUST 21:  Chase Headley #7 of the San Diego Padres hits a walk-off home run in the 10th inning of a baseball game against the Pittsburgh Pirates at Petco Park on August 21, 2012 in San Diego, California. The Padres won 7-5.  (Photo by Denis Poroy/Getty Images)
Denis Poroy/Getty Images

With Alex Rodriguez coming off a second major hip surgery and in the middle of MLB's latest PED scandal to boot, the New York Yankees clearly need a long-term solution at third base.

That means you, Chase Headley.


Headley stands out as a brilliant solution to the Yankees' third base issues, but there's one problem: He's still employed by the San Diego Padres. If the Yankees want him, they either have to trade for him or wait to sign him after he becomes a free agent in 2015.

Jason A. Churchill wrote in an ESPN Insider post that the Yankees could be among the first teams in line for Headley if he does hit the trading block, thus continuing a proud tradition of speculation that Headley will end up on the Yankees eventually.

Ever since ESPN's Buster Olney reported last July that the Yankees were considering making a run at Headley, fans and writers have been sizing him up for pinstripes, and understandably so. The Yankees' problem at third base is clear and present and Headley's talent level skyrocketed in 2012.

After never hitting more than 12 home runs or posting an OPS higher than .773, Headley managed an .875 OPS and 31 homers in 2012. Not bad for a guy who's had to play half his games at Petco Park, and Headley was also good enough in the field to win his first Gold Glove (for what it's worth).

Among third basemen, only David Wright managed a higher WAR than Headley by FanGraphs' reckoning. The guy directly below him in the rankings won the MVP over in the American League.

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So yeah, Headley's good. And like all good players, he's going to get paid. Hence the reason for all the trade speculation, as Headley plays for a team that probably can't afford to pay him.

The Padres are on the hook to pay Headley over $5 million more than they paid him in 2012 after avoiding arbitration with an $8.575 million contract last week. With him due for free agency after 2014, the pressure is on the Padres to hammer out an extension if they want to keep him.

And that's not likely to happen. They may have new owners, but the Padres are an organization with limited financial resources. They also know that Headley isn't about to give them a discount with free agency nearly close enough to touch.

“We talked about a long-term contract briefly at the start of these negotiations,” Headley told Bill Center of the San Diego Union-Tribune in reference to his recent contract talks. “It was a quick discussion. We weren’t on the same page right from the start. This close to free agency, it has to be a good deal for us. You can’t sacrifice what’s fair."

There will be pressure on San Diego GM Josh Byrnes to swing Headley for prospects at the deadline if the Padres are out of it, and the pressure will be all the more intense if Headley proceeds to keep raising his trade and free-agent value by putting up big numbers.

And that's where the Yankees could come in. 

The Yankees will have a tough decision to make on the Headley trade front if Kevin Youkilis ends up being surprisingly productive in A-Rod's stead, and there's a fair chance that will happen. A close look at the numbers reveals that Youk was a better player than Rodriguez after he joined the Chicago White Sox. If he stays healthy in 2013, the Yankees won't miss Rodriguez in the slightest.

But the Yankees' need for a long-term answer at third base will still be there. Youkilis is only signed for one year, and Rodriguez's future with the Yankees is uncertain no matter which way you cut it.

The Yankees could void A-Rod's contract if MLB punishes him for the latest PED mess. Or he could be forced into an early retirement by his health, in which case insurance would pay for most of his contract. Even if he does keep playing, he's most likely to finish his career as a full-time DH rather than as a full-time third baseman. 

But if the Yankees have already put Headley on top of their third base wish list, they don't necessarily have to trade for him. They could just wait patiently for him to hit free agency in 2015.

There could  be very little to stop them from doing so, as the Yankees won't have to pay a high luxury tax if they follow through on their plan to get under the $189 million threshold in 2014. Furthermore, they only have three guaranteed contracts on the line for the 2015 season at a total of $68.125 million.

That number isn't going to increase all that much if Robinson Cano walks as a free agent after 2013, which the New York Daily News has warned could happen. The Yankees could also finally part ways with Derek Jeter after 2014, or maybe even before then if he declines his player option for '14 and then demands too much money.

If the Yankees don't add many (or any) big contracts to their 2015 commitments, then they'll have more than enough coin to go after Headley with a long-term offer in free agency. He'll be on the wrong side of 30, sure, but the fact that no position player has gotten a deal for longer than five years this offseason could be a sign that longer commitments to free agents are going out of style.

Choosing to wait, however, is not a foolproof plan. There's pressure on the Yankees to win every year, and the fans aren't going to be happy if the team signs another stopgap third baseman—or worse, sticks with A-Rod—for the 2014 season before going after Headley in 2015.

But the bigger potential pitfall involves another team trading for Headley and then inking him to an extension worth the kind of fair-market-value money he wants. This is a very real risk, as even poor teams are going to have new national TV money to throw around starting in 2014.

So if the Yankees want Headley, odds are they understand their best bet is trading for him. Making it happen is a matter of a) Headley hitting the block and b) Brian Cashman coming to grips with the fact that he'll have to wave goodbye to some top prospects.

This is something that Cashman is going to be loath to do. He and Gene Michael built the Yankees into a powerhouse by holding George Steinbrenner at bay and allowing the club's farm system to graduate young talent to the majors. Current team boss Hal Steinbrenner has indicated that he's in favor of developing homegrown talent, as homegrown players are cheap and good for the budget.

But Cashman will have the pieces to go get Headley in a trade. The Yankees farm system isn't regarded as elite, but ESPN's Keith Law (Insider post) has deemed it to be better than advertised. He has the Yankees farm system ranked as the No. 10 system in baseball, and he praised it for having an abundance of talent at the lower-levels.

Low-level talent could suit the Padres just fine in a trade. They saw several of their top youngsters make the jump to the majors in 2012, and they should have a few more make the jump in 2013. They're set to have a team littered with homegrown talent, which is great, but the ranks down below must be replenished.

The bidding for Headley, however, is sure to be fierce enough to drive the price up. Churchill speculated that the Chicago Cubs, Boston Red Sox and Los Angeles Dodgers could get involved as well. The Cubs and Red Sox both have talented young players coming through the pipeline they could part with, and the Dodgers have limitless financial resources that they don't mind using (unlike the Yankees).

If the asking price gets too high for Cashman's liking, don't think for a second he won't be willing to walk away. Headley's a great player, but he's only one great player. If Cashman sells the farm for him, the organization would find itself with a shortage of young players down below. 

The Yankees have more incentive to keep their farm system intact than ever before. They've relied on patching holes with free agents for years, but free-agent classes are becoming unspectacular thanks to the fact that teams now have TV money with which to extend their homegrown players.

Combine this reality with the fact that the Yankees are going to see a fair number of veterans depart in the next few years, and it's clear that they need a strong farm system more than they need one long-term star.

I have zero reservations about guaranteeing that the Yankees will be in on Headley if the Padres fall out of the race in 2013 and put him on the block. Even if Youkilis is performing well and Rodriguez is on the comeback trail, the Yankees will see a chance to acquire one of the game's top third basemen.

But since the Yankees have resisted shipping off prospects for star players ever since the trade deadline despite have chances to do so, they've shown that they're going to be careful about letting their lust for star players overrule their better judgment in regards to their long-term future.

The Yankees will walk away if the price for Headley gets too high in trade negotiations. And be warned: It's going to be high.

Note: Stats courtesy of Baseball-Reference.com. Salary and contract info courtesy of Cot's Baseball Contracts.

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