Let me pose this hypothetical to you. Let’s say that I have what every Manager and General Manager in Baseball wishes they had (and every fan thinks they have) and that is a crystal ball. One that can see into the future. Seeing not just what we wish to happen, but seeing all, the good and the bad.
As I gaze deeply into my crystal ball, I see the Yankees making the Roy Halladay trade. They give up Joba, Montero and A-Jax to complete the deal. Roy Halladay comes to the Bronx and is brilliant from Day 1. He leads them to the playoffs each of the next 3 years, leaving the Red Sox and Rays in the dust. John Henry Twitters that he hates Baseball, and should have never bought the team. The Yankees will win 2 of the next 3 World Series, appearing in all three. Halladay pitches brilliantly in the post season, winning decisive games and closing out the final game of the 2009 World Series with a complete game shutout. Joy and celebration reign in the Bronx.
But wait, now I’m looking deeper into my crystal ball. I see Jesus Montero becoming the next Frank Thomas, Austin Jackson playing like Devon White and Joba, oh boy is he good. Joba Chamberlain has worked through his early adjustments and is pitching like Roger Clemens in his prime.
I’m not done yet. After winning 2 of the next 3 World Series championships, the Yanks collapse 1964-style in 2012 when Jeter, Mo, Posada (and yes) A-Rod all get old at the same time. They have the resources to field a decent team, but it’s the 1980′s all over again. They have no high-end reinforcements coming from the farm to compete with the Rays, Red Sox and the up and coming Blue Jays. They have a sub-.500 for the next 5 seasons, finishing in 4th place most of those seasons and one year in dead last.
The Blue Jays however, are flying high. They make three straight World Series appearances from 2013-2015 due in large part to the three stars we traded them for Halladay. Jesus Montero is is named the 2014 AL MVP, putting up a monster .350/.402/.698 season with 54 HRs and 148 RBIs. Joba Chamberlain is the 2013 World Series MVP, winning 3 games with (yes) a 0.38 ERA.
OK, back to 2009. You’re Brian Cashman, standing at the crossroads. Do you make the Roy Halladay trade?
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