Boston drafted Westmoreland, then a prep phenom, in the fifth round of the 2008 Draft, convincing him to forgo his college commitment to Vanderbilt University with a $2 million signing bonus.
The Newport, R.I., native acquitted himself well in his lone season, in 2009. A left-handed hitting outfielder, he posted an .885 OPS and stole 19 bases in 60 games for Class A Short-Season Lowell.
The following March (after Baseball America named him the No. 21 prospect in all of baseball), he underwent surgery to remove a cavernous malformation from the stem of his brain. A second surgery took place last July.
"With a clear mind and heart, as well as the unwavering support and friendship of my family, friends, agent(s), doctors, therapists and the Boston Red Sox, I have decided to voluntarily retire as a professional baseball player," Westmoreland wrote in an email to several members of the media. "Although it is a very difficult decision for me, it has become clear that the neurological damage caused by the most recent cavernous malformation and surgery leaves me with physical challenges that make it impossible to play the game at such a high level.
"In my heart, I know that I have worked as hard as one possibly could to overcome the obstacles presented by this unfortunate series of events. It is with that confidence that I am comfortable turning the page, and searching for 'the reason' that this has happened. I believe that there is a plan for me that will utilize my experiences, however painful some may have been, to do something special in my life. It is time for me to find that path and to pursue it with the same focus and effort that I pursued the dream of playing professional baseball.
"Regardless of this result, I have been very fortunate throughout my professional career and the last three years of recovery and rehabilitation. I have met sincere, caring people that have believed in me and have helped me to stay focused on the task at hand. I will never be able to adequately thank the wonderful people in the Boston Red Sox organization, that continued to support me and my family throughout all of this. From the time of the initial diagnosis, it was never about the baseball. They cared for me as a person... a member of their family, and their focus was entirely on my physical and emotional well being.
"I have met so many players that have been there for me, that I know will continue to be my friends long past this. I have had access to the best hospitals, doctors, surgeons, therapists and others that, without their professional advice and treatment, would never be where I am today. Octagon has always been more than a sports agent to me, they are friends that were there in every hospital or whenever I needed them for support and advice. The media has been fair and sensitive to me throughout this, and I am grateful for that. Through that media, I have been blessed to receive support and encouragement from so many people from all over, that although I don't know them have been instrumental in driving me to accomplish all that is possible.
"And finally, my family and friends have been by my side and have supported whatever it is that I wanted to pursue. It has been a difficult road for all of them, yet they have managed to stay strong and keep me focused on the next goal. I have no doubt their support will continue to drive me towards the next."