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Sources say Headley for Upton swap has been discussed 

Chase Headley

You just never know what you might come across on the internet. Today a brief post on MLBTR really caught my attention. Citing “major league sources,” Zach Links writes that a potential deal involving Padres 3B Chase Headley going to the Diamondbacks in exchange for OF Justin Upton has been discussed on and off since last July.

That rumored deal probably made a lot more sense this summer than it does now given Headley is coming off a career season in which he was the NL Gold Glove recipient and won a Silver Slugger award. Upton meanwhile is coming off a down year in which he posted an OPS mark of .785. That’s a full 90 points less than that posted by Headley.

Assuming the reports are true, the rumor does make some sense. Arizona has been clamoring for a long-term answer at 3B and have been entertaining offers for Upton for quite some time. Arizona GM Kevin Towers drafted Headley when he was GM of the Friars and presumably still holds him in high regard. Padres GM Josh Byrnes was the GM in Arizona when the club signed Upton to his first professional contract. (Note: Byrnes was hired as the Arizona GM in November of 2005 and Upton was drafted by the club in June of that year. However Upton didn’t sign until January 6, 2006 when Byrnes was the GM.)

The Padres do have top prospect Jedd Gyorko they could install at 3B should they deal Headley and the Diamondbacks have a plethora of OF options if they find a deal involving Upton to their liking.

Headley is arbitration eligible and has been projected by Matt Swartz of MLBTR to earn $8.3MM on his third trip through the process. Upton is under contract for three more seasons at a total cost of $38.5MM. It’s likely that Headley would earn less than that total for the same period of time.

The potential move does make at least some sense on some levels but at this point I find it unlikely any deal involving those two players goes through this winter. Headley’s trade value has never been higher, he’s almost certain to cost less for at least the next two seasons of team control that remain and the Padres seem otherwise set at the OF position.

While you chew on that little tidbit, I will get back to work on some research. Since I hate to rely solely on first impressions I will post a piece at a later date comparing Upton and Headley in a more detailed manner.



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.

  • Beersy

    How has this been kept quite since July? Looks to me as though Rosenthal had nothing to write about as we are in the dog days of the off season, so why not throw some spicy little story out there. If this deal was really discussed, pretty sure it hasn’t been since July because of the way Headley went off in August and September.

    • Glen Miller

      The “sources” weren’t named but it wouldn’t surprise me at all if there was a brief discussion in July followed by Towers approaching Byrnes more recently about the same. I’m sure Byrnes would decline that overture at this point.

  • Beersy

    More importantly Glen, Bill Center is reporting that the Marlins have contacted the Padres about a deal involving Stanton. If the Marlins are calling, that would make you think they are smitten with a couple of the Padres prospects. IMO a deal that would bring in Stanton would trump any deal involving Upton, and that doesn’t even include the fact that Headley would not be involved in a Stanton deal. Lets go Mr. Byrnes, it’s time for another monster deal. 🙂

    • Glen Miller

      I think my position on possibly acquiring Stanton is clear. Where did Center make those comments; on Twitter or in an article on UT?

      • Beersy

        He says it in the Padre Insider in the UT today. I realize you are all for a Stanton deal, but you and I wishing/hoping for it, is a lot different than it being discussed by Byrnes and Beinfest discussing it.

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