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Halladay Shopping

Roy Halladay (Photo Courtesy of

Should Theo Part with Buchholz and Kelly for Toronto Ace?

Black Friday is still a couple days away but the Red Sox have already begun their offseason shopping. Boston is working on a potential deal that would land them former Cy Young award winner Roy Halladay.

The New York Daily News first reported the Sox were a  “putting a full court press” on acquiring Halladay and would like to reach a deal before the winter meetings begin on Dec. 7. If the report is true, the Blue Jays seem to be implementing their own type of press break. The play might be called Casey Kelly.

The Daily News, as well as The Boston Globe, are reporting the Jays are demanding Kelly, who is far and above Boston’s No. 1 prospect and Clay Buchholz .  If those are the demands and Toronto is unwilling to budge, don’t expect the deal to get done.

Too Steep a Price For Theo

During his tenure as General Manager, Theo Epstein has been hesitant in trading any of his prized possessions on the farm. When Hanley Ramirez was dealt to Florida for Josh Beckett and Mike Lowell, it technically wasn’t on Epstein’s watch as he had stepped down because of a dispute between himself and Larry Lucchino.

Ramirez is even on the record saying he believes Theo never wanted to trade him.

The Ramirez deal was four years ago, but Espstein’s unwillingness to deal his top prospects was seen last year too. The Sox were willing to send a boat load of talent to Seattle in an attempt to acquire a Felix Hernandez, a player nearly a decade younger than Halladay but with just as much talent. Even then, amongst a smorgasbord of Red Sox talent: Clay Buccholz, Daniel Bard, Michael Bowden, Justin Masterson, Nick Hagadon, Josh Reddick, Felix Doubront and Yamaico Navarro…one name not on that list — Casey Kelly.

The question arises: if Epstein wasn’t willing to put Kelly on the table for Hernandez, a younger player who had better numbers than Halladay last year, and is under contract until 2011, why would he throw Kelly in a deal now?

Kelly’s Too Valuable a Piece

If Theo is willing to give up his crown jewel, it shouldn’t be on a soon-to-be 33 year old pitcher. Granted, a deal involving Halladay would almost have to come with an extension, but that’s still not be enough.

Toronto is likely going to have Buchholz and Kelly under their control for about the same time the Sox would have Halladay. The only difference is Buchholz and Kelly would be entering primes of their respective careers while Halladay would be entering the twilight of his.

Not to mention, the Sox could have to face the two upwards of 8 to 10 times a year. The same is obviously true for Toronto. The Sox would be getting one of the elite pitchers in the game, but is it actually possible to acquire someone better?

If the Sox are already committed to the notion that Kelly is tradable, then  package Buchholz and Kelly along with other prospects for Hernandez or Adrian Gonzalez.

Judging by what happened at last year’s trade deadline with Seattle, Boston, and San Diego, Hernandez and Gonzalez might be available, especially Gonzalez. The Padres were all set to trade the face of their franchise until Seattle backed out.

A bat in the middle of the lineup is a much more pressing need and the Red Sox would have Gonzalez under contract until 2011. The same is true with Hernandez. It would take more pieces to acquire these players, but the production the Sox would  get would be more. Hernandez and Gonzalez are years away from turning 30 and are entering the prime of their careers.

Another bright spot in dealing with San Diego or Seattle is playing against San Diego and Seattle.  If Buchholz and Kelly do pan out the way people think they will, Boston would hardly ever face them. The Red Sox play San Diego once in a blue moon and with schedules geared more towards playing divisional foes, the Sox only face the Mariners twice a year.

But It Does Take Two to Tango

Perhaps Epstein and Co. already talked with San Diego and Seattle, and Gonzalez and Hernandez are off limits. Judging by the past, Hernandez might be, but Gonzalez seems to be available for the taking for the right price. With a starting rotation of Josh Beckett, Jon Lester, Daisuke Matsuzaka, maybe Clay Buchholz along with the talent in the farm system, the staff is headed in the right direction.

Right now most teams are salivating over Kelly and would want a package including him. There is an awful lot of smoke created by Boston currently and in the past dealing with Halladay and Gonzalez. Either player would improve the Sox exponentially. Will all that smoke eventually evolve into fire or will Kelly, who isn’t old enough to buy an alcoholic beverage, extinguish any hopes of a blockbuster trade?

Epstein has the match in his hands, we all have to sit back now and see if he strikes against a surface to ignite it.

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5 comments for “Halladay Shopping”

  1. Halladay Shopping: Should Theo Part with Buchholz and Kelly for Toronto Ace?
    Black Friday is still a couple days …

    Posted by Sports of Boston | November 25, 2009, 6:50 pm
  2. I think I’d only trade Buchholz and Kelly for Felix, or maybe Albert Pujols. That’s it. Just those two. I’d consider Grienke, but he still has to prove himself more.

    Adrian Gonzalez is good, but I think the Sox have enough to get him without giving up Kelly OR Buchholz.

    I’d be willing to send Buchholz to the Jays for Halladay, but not both him and Kelly. The Sox have to hold onto Kelly if possible.

    I got an idea: instead of trading for Halladay, why don’t the Sox sign John Lackey, Jason Bay, and trade the prospects for either Gonzalez or Miguel Cabrera? Yeah, I know that situation is too ideal haha.

    Posted by KC | November 26, 2009, 5:41 am
  3. trade casey kelly and buchholz to florida and get hanley back, thus fixing our short stop problem and getting a big bat back in the lineup.

    Oh, problem solved.

    Posted by Pete | November 26, 2009, 12:48 pm
  4. […] the big spenders in the offseason. They are currently looking at some big name players to come in, including Roy Halladay. However, Boston has a great farm system and could always bring someone in midseason as they have […]

    Posted by Holliday or Bay? The Sox Have Choices | Sports of Boston | November 27, 2009, 8:42 am
  5. […] so youth in the rotation would be nonexistent outside of Jon Lester.  It would also take them out of the running for Roy Halladay, which might not be a bad thing […]

    Posted by Hanley Ramirez Would Look Good in Red Sox | Sports of Boston | December 2, 2009, 4:19 pm

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