Drafted: Fifth Round, 2008 (Portsmouth, RI)
Height: 6′2″; Weight: 195 lbs
Born: April 27, 1990
This is where I choose to slot Westmoreland. While his future is in question following his recent surgery, his talent is too great to ignore…but there are too many questions in play to slot him ahead of Kelly, Reddick, or Kalish.
Westmoreland drew relatively little interest as a high school senior due to a plethora of reasons… but the Sox drafted him in the fifth round nonetheless. The ballclub realized the gamble paid off after Ryan hit .557 for the Bayside Yankees, one of the nation’s top amateur teams, during the summer of 2008. They paid him $2 million in a signing bonus to get him under contract prior to the Aug. 15 signing deadline…Vanderbilt University’s loss was the Red Sox’ gain.
Former Red Sox scouting director Jason MacLeod once said that Westmoreland has more upside than any player he had ever selected in the big league draft. He has a compact, powerful swing and good command of the strike zone. He makes consistent and solid contact. He has plus-plus speed, stealing 19 bases at Lowell (SS) last year without being caught. He has plus range in the outfield, but needs to work on his throwing mechanics.
The scouts have said that all he needs is time…However, due to the recently-discovered cavernous malformation on his brain stem, the timetable for his development obviously has to be modified.
His future on the baseball field obviously takes a backseat to other considerations at this point, and I even considered leaving him off my list all together (although I ultimately decided to leave him here, at a lower ranking). My prayers are with him and his family as he works to recover from surgery.