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The Roy Halladay Trade Sweepstakes

Quite possibly the most season-altering move a team could make would be trading for an ace before the deadline to fulfill a hole in the starting rotation. We saw the benefits of that for Milwaukee last year when they acquired C.C. Sabathia and rode his arm into the playoffs. Well, fortunately for us rumor mill enthusiasts, Toronto announced they would listen to offers for Roy Halladay. Now while they won’t go out of their way to send out their No. 1 starter, the Jays will make a trade if they get what they’re asking for. So, I’m going to try and determine if any teams will get the deal done this year.

The two obvious competitors for any high profile name are the New York Yankees and the Boston Red Sox.  Two of the richest teams in the game (Boston and New York) always tend to be after the top player. However, the Blue Jays are averse to dealing within the division. Halladay has a full year left on his contract after this season and the Blue Jays don’t want him to be the reason they can’t compete in the division next year. Plus, the fans in Toronto are already struggling to find a reason to cheer the team and trading him within the division would make for an easy fan defection route.


The Yankees are unlikely to do a deal unless the price is very nice. After all, they held back on trading for Johan Santana. Plus, Brian Cashman didn’t hold on to his young talent to just trade them away after a short term period of not living up to the hype. A Yankees trade would potentially thin out the upper levels of their farm system as well, a goal counter intuitive to Cashman, who’s probably trying to bring a more palatable number to his salary.

Red Sox

The Red Sox have the room financially and the talent to trade. However, given their starting pitching depth (Clay Buchholz, Junichi Tazawa and Michael Bowden as backup starters and Justin Masterson in the pen able to be stretched out, Daisuke Matsuzaka coming back from injury), they’re not struggling to find a pitcher, though there is no guarantee any of those guys will pitch at a Halladay level. But, you would have to figure that because of their reluctance to trade in the division, the Blue Jays might ask for a little more of both the Red Sox and Yankees. So that puts the odds for both at very low.


The team with the next highest payroll and wallet is the Mets. The biggest issue for the Mets, outside of their poor play, is not having much of a farm system. Omar Minaya has stripped away the little depth the Mets had in the trades for Santana and Putz. One of their top prospects, Fernando Martinez has shown he’s far from qualifying as a major league-ready prospect. The Mets are not going to be a player this time around.

White Sox

The White Sox do have the salary cap room to acquire Halladay and they are competing and did nearly complete a trade for Jake Peavy. However, the White Sox can’t afford to trade Gordon Beckham and without trading him, I can’t see the Blue Jays accepting a deal. All rumors so far have mentioned the Blue Jays looking for a high level position player and Beckham is the only one the White Sox can trade. So, I don’t see the chances of the White Sox pulling this off as very high.


The Los Angeles Angels are a team in need of starting pitching, given the loss of Kelvim Escobar from the rotation for the year and how poorly Ervin Santana and Joe Saunders have pitched. Arte Moreno has shown a willingness to spend money, as well. The Angels farm system is not quite as deep as it used to be (though it’s far from barren, just a little bottom heavy) and Brandon Wood has shown massive, exploitable holes in his swing in the majors. So a trade would likely have to be centered around a different player. The Angels are a bit of a possibility.


Another team where there could be a good fit is the team that just signed Pedro Martinez, the Philadelphia Phillies. Philadelphia can increase their payroll, has a need at starting pitcher, even with Pedro, and have a good infield prospect (and one who is blocked by the current middle infielders) in Jason Donald. Plus, with Pat Gillick around, there may still be connections around from Pat’s days as Blue Jays GM, which will make trade talks easier. I pick the Phillies as the favorites to acquire Halladay if he’s traded.

The Rest of Baseball

Finally, to just give an idea of the rest of the field’s little chances of pulling off the trade, I will point out why they won’t acquire Halladay.

  • The Rays don’t have the ability to add that much payroll to their team.
  • The Tigers likely don’t have the ability to add that much payroll for this year, don’t really have the talent to trade and don’t need starting pitching as much as they need hitting.
  • The Twins ownership won’t allow the team to ever add that much payroll and they don’t have enough in the farm system to be able to acquire Halladay.
  • The Mariners are more likely to build for next year when more of the prospects are closer.
  • The Rangers probably can’t add the salary for Halladay given how the organization had to borrow money from MLB.
  • The  Braves need hitting more than pitching and probably don’t want to add that much salary to their payroll, given their past tendencies.
  • The Dodgers almost definitely have the NL West won and just need to stay healthy. Halladay would be a huge help for the playoffs, but their offense can still do a good enough job to give them a good shot.
  • The Giants need hitting more than pitching.
  • Halladay would almost definitely veto a trade to Colorado.
  • The Cardinals need a hitter more than a pitcher.
  • The Brewers need a starter, but probably don’t have the ability to add the salary, due to next year’s salary for Halladay being on the books also.
  • The Astros are pretenders, not contenders.
  • The Cubs are not going to compete this year.

And finally, every other team is either too poor, too unwilling to spend the money, or completely out of the race.

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3 comments for “The Roy Halladay Trade Sweepstakes”

  1. […] The Roy Halladay Trade Sweepstakes […]

    Posted by Halladay Dominates Red Sox in 3-1 Win | Sports of Boston | July 20, 2009, 6:08 pm
  2. […] Brewers’ GM, Doug Melvin, offers his take on the Brew Crews’ chances. And finally, talks about Halladay as a Red Sock (sp?) and they give their take on the likeliness of him ending […]

    Posted by iSportacus » Blog Archive » The Roy Halladay Link Dump | July 23, 2009, 12:21 pm
  3. […] a comment I’m sure I’m not the only one who gets mightily sick of hearing about possible trades for Roy Halladay. The saga has been dragging on for what seems like decades, with the same names being bandied about […]

    Posted by OMG. DON’T LET TEH YANKEES GET HALLADAY. SRSLY. | Sports of Boston | July 26, 2009, 11:41 am

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