The Red Sox will have three shots at a Gold Glove this year, with Dustin Pedroia, Yoenis Cespedes, and Jackie Bradley Jr. being named finalists for second base, left field, and center field respectively.
For Pedroia, this is nothing new. He's constantly in the mix, and should probably win more often than he does, even with three already to his name. If he wants to make it four, Pedroia will have to beat out Ian Kinsler and Robinson Cano--strong competition when you consider that these awards tend to only be about 30% fielding with the rest made up by some combination of offense and name recognition.
Jackie Bradley Jr. did not have the best of years, but his presence here is also not terribly surprising. For all that he couldn't hit, and was eventually supplanted by the all-around excellent Mookie Betts, Bradley was a
walking running highlight reel in the field, making difficult catches look easy and nigh-impossible catches look spectacular. He'll face the same issues as Pedroia in toppling his competition in Adam Jones and Adam Eaton, but a Gold Glove award would be a nice way to finish off a disappointing season.
The weird choice here is Yoenis Cespedes, though given that he's facing off against Michael Brantley maybe Rawlings just really likes outfielders with arms? Cespedes is a reasonable corner outfielder with that highlight cannon of his, but really this one should just be going to the third candidate in Kansas City's Alex Gordon. Or, better yet, they could do away with left field and right field Golden Gloves and just have outfield Golden Gloves.
Then again, these awards seem to be chosen more-or-less arbitrarily, so maybe there are bigger issues to fix than just that.