New York Yankees General Manager Brian Cashman has been smart in some ways.
Other times, he hasn’t been too smart.
At the trade deadline, or at least this off-season, the Yankees should have acquired ace starting pitcher Roy Halladay when he was with the Toronto Blue Jays.
Before July 31, the Yankees might’ve needed to give up three or four prospects.
But in the offseason, Cashman could have made a deal that would have been news everywhere: trade Austin Jackson, Joba Chamberlain, and Arodys Vizcaino for Halladay.
Roy Halladay had one year left on his contract, but of course the Yankees could lock him up. Not only do the bright lights of New York attract him, the history of winning on the team made Halladay think the Yanks were a possibility to be a place where he could land.
Just imagine this: Roy Halladay, followed by C.C. Sabathia, A.J. Burnett, Andy Pettitte, and Phil Hughes.
With this trade, the Blue Jays could’ve gotten a great deal to rebuild.
Joba Chamberlain
Joba Chamberlain is a pitcher that many consider to be one of the best prospects in the game today. The Blue Jays would have been very happy to have him. But Cashman had to be stubborn, and he stayed with Chamberlain.
Here’s the theory:
Let’s say Chamberlain becomes the next 20-game winner. The Yankees will still have maybe the best rotation for the 2010 season.
Austin Jackson
Austin Jackson is excelling at the lead-off spot as a Detroit Tiger. Even though the Blue Jays had Vernon Wells at center field, Jackson could’ve been placed in right or left field.
Arodys Vizcaino
He was the best relief prospect pitcher on the Yankees. Then, Cashman trades him and Melky Cabrera for Boone Logan (who seems to have no future as a Major League pitcher) and Javier Vasquez, who struggled for a month.
For the weak Toronto bullpen, Vizcaino could have been up in the big leagues after a year in the minors for some tune up.
Roy Halladay should currently be a New York Yankee.
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