The Red Sox might be asking themselves the same question. Former Diamondbacks general manager Josh Byrnes, who signed Upton to that contract and these days is in a neutral position (though he may hook on somewhere, maybe even Boston, as a special assistant), is a big believer in Upton’s future.
If the Sox want to make a splash, well, either Gonzalez or Upton could be a tsunami.
Gonzalez is now going into his final season before free agency, and the teams that have shown interest in him in the past include the White Sox, Cubs, Orioles, Nationals, and Red Sox. Somehow, that will not be the case with Justin Upton, currently the outfielder for the Arizona Diamondbacks.
In fact, trading for Upton is exactly the best kind of trade the Red Sox [team stats] could make, and for all the right reasons.
It may be harder to predict what the Red Sox are going to do than project the career of the 23-year-old Upton. Based on early indications, Jacoby Ellsbury [stats] and Daniel Bard would be two key parts of any Upton deal.
The Sox’ offensive core consists of Kevin Youkilis [stats], Dustin Pedroia [stats] and Ellsbury. Kalish is just seven months younger than Upton, and Rizzo and Iglesias are a couple of years younger.
Maybe Kalish would have to go in an Upton deal as well, it wouldn’t be surprising, but inject Upton into the heart of the current Red Sox lineup, and you win.
Upton is not perfect. Guaranteed - if the Sox decide not to deal for Upton, another team will.
Guaranteed - if the Sox deal for Upton plus sign one of the big four or make another addition they know they can make, then they win this deal as much as the Diamondbacks.
For all the right reasons, the Red Sox need to make the trade that brings Upton to Boston.
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