Former Red Sox prospect Ryan Westmoreland married his fiancée, Libby, in Newport

Once a top prospect, Westmoreland has had to undergo several brain surgeries that forced him to retire.

Former Red Sox prospect and now UMass Dartmouth baseball assistant coach Ryan Westmoreland married his fiancée, Libby, on Friday in Newport, Rhode Island.

The couple, who got engaged in 2018, had postponed their original wedding plans and instead opted for a local wedding with their close family and friends. According to Libby’s latest instagram post, the Westmorelands plan on having another reception in July of 2021.

“There were so many important people missing, and it was certainly not the same without you, but we felt so loved, even from afar,” she wrote. “And we feel so lucky to get to do this all again on 7.8.21!”


Ryan also shared photographs of their wedding — with a stunning view of the ocean — on Twitter:

The ceremonious occasion marks an uplifting moment for the couple, who have dealt with the emotional toil of Ryan’s health over the years.

In a feature story by The Boston Globe’s Stan Grossfeld, Ryan talked about the 10 years since he underwent emergency brain surgery after doctors found a cavernous malformation. Only 19 years old at the time, he had been drafted by the Red Sox out of Portsmouth (R.I.) High School in the fifth round only two years prior — and was considered one of the top prospects and regarded as a “left-handed Mike Trout.”

His health did improve, and he was able to return to the baseball field and take swings against professional pitchers in the Dominican Instructional League in 2011. Unfortunately, the tumor re-formed the following year, and he underwent a second surgery to successfully remove it. Once the Red Sox’ No. 1 prospect, he retired from baseball at the age of 22.

He has undergone 17 brain-related surgeries so far.

Ryan, or “Westy” as he’s often called, admitted that the mental pain became too much for him at times. He even stopped watching Red Sox games — feeling that it was too painful to see teammates he had played with in the minors, such as Jackie Bradley Jr. and Xander Bogaerts, while knowing that he was supposed to be alongside them.


Despite setbacks that still effect him today, including numbness on the right side of his body and face, he has continued to work with doctors and is focused on maintaining his health through training and nutrition. He’s steadily improving, including looking “ripped” and being able to “move easily with just a slight limp.”

His mental health has improved, too, thanks to the support of his family and Libby. The two met on an online dating app, and Ryan said that he admires his wife, who is a social worker, for her emotional strength.

“She’s incredible,” Westmoreland told the Globe‘s Stan Grossfeld. “She’s very in tune with emotions and how to deal with trauma and different aspects of life.”

Baseball has also remained in his life, through coaching youth summer league, at Portsmouth High School, and now at UMass Dartmouth. Having experienced the love and loss of having the game taken away from him, Ryan shares his experience with younger athletes and hopes to help them “in life” as well.

Around the time of the anniversary of his diagnosis, he often has a vivid dream of playing at Fenway:

“I just dreamed of running out to center field at Fenway with a packed house,” he said. “Everything is silent and in slow motion. I’m just seeing everyone and thinking ‘I made it!’”

Jump To Comments