Ryan Westmoreland

Ryan probably doesn't remember this, but my first memory of him was back in the summer of 2005.

I was 19, playing for the Newport Gulls, where his father, Ron, was one of the owners. During batting practice, I was shagging balls in the outfield when I noticed this 15-year-old kid flying around catching everything. Effortless, joyful, making it look easy.

I turned to my teammates with a smirk: "This kid is better than half the guys in this league." A league filled with future draft picks and big leaguers.

A few years later, he was drafted by the Red Sox and became one of the top prospects in all of baseball at 18 years old.

Ryan was kind enough to share his story and offer advice to parents and young players on what really matters.

Ryan was on the fast track. A scout once compared him to Mickey Mantle.

Portsmouth High School star. Two-time Rhode Island Gatorade Player of the Year. Committed to Vanderbilt. Then the Boston Red Sox came calling with a $2 million signing bonus in the 5th round of the 2008 draft.

By 2010, Baseball America ranked him the 21st-best prospect in all of baseball.

Then everything changed.

A cavernous malformation at his brainstem. Two brain surgeries. Years of rehabilitation. Retirement at 22 years old.

Today, Ryan coaches at UMass Dartmouth and in youth baseball. His story about what it takes to be elite, what happens when it all gets taken away, and why identity matters more than stats. That's what parents and young players need to hear.

Ryan Westmoreland's Journey:

In this feature, Ryan breaks down:

Here's our conversation.

You were a two-time Rhode Island Gatorade Player of the Year and highly recruited. What separated you from other talented players in Rhode Island and across the country during those high school years?

Almost every coach that recruited me mentioned how much it meant that I was a multi-sport athlete who excelled in other sports. They could tell I dedicated my time and focus to whatever sport I was playing in a given season. I was never a guy that believed in playing one sport year-round—I wanted to compete and have fun with my friends, which made me a more well-rounded athlete and competitor.

On the baseball side, a few characteristics jumped out to scouts. I was a big body at 6'3" but could still run really well: 6.2-second 60-yard dash. I had good arm strength and could hit to all fields, but if I had to choose one characteristic, it was my speed that really caught their eyes.

You were an all-around athlete who played multiple sports. Do you think that's still important for kids coming up today? Do you think that helped you be a better baseball player?

Absolutely. Playing multiple sports teaches leadership, teamwork, accountability, and different forms of competition. Fall was soccer. Winter was basketball. Spring and summer were baseball. I never overlapped those seasons—never missed basketball practice to go to the batting cages with my dad. That mindset helped me be a better baseball player because I could take mental and physical breaks, which is healthy for a kid feeling the weight of MLB and college scouts.

Besides your natural talent, did you always put in the extra work? What was your mentality like growing up? Help me understand your mindset.

I honestly just always loved to play baseball. I loved to play with my friends. When I was younger, my drive was never "I need to work hard to make it to the Major Leagues"—it was just that I love this and it's fun so I want to be here.

As I got older, I put more time into certain aspects of my game. When I was getting scouted by MLB, I started working in the batting cage with extremely high velocities, but it never felt like a burden. It was something I wanted to do and wanted to work on.

I was fortunate to have natural ability, but I never felt like "I have to take advantage of this and make it to the MLB." I just loved playing and let the chips fall.

You went from being a top prospect with everyone watching you, to fighting through surgeries while your teammates moved on in their careers. How did that change your understanding of what it means to be a good teammate? What do you teach young players about being a teammate when they're not the star?

I'll admit, right after my surgeries I wouldn't watch any baseball because it was too painful knowing I was on the fast track to The Show and suddenly I wasn't. It was hard to be a good teammate during that time, but eventually when I saw guys I played with get called up, I was excited for them. I realized how unbelievable it would feel to get that call to the major leagues, so I was nothing but happy for them.

When I'm coaching now, I always preach the importance of teamwork. Baseball is a game where you can't win it with just one person. You need all 9 working together. Whether you're the most talented or least talented person on the team, the team still needs you. It's a team game for a reason.

Who were the coaches or mentors in your development—from youth ball through the Red Sox organization—who had the biggest impact on you? What did they teach you?

Up until pro ball, there's no question my father, Ron, had the biggest impact on me. He played baseball growing up and in college, and it's a big part of why I love it so much. But he never forced me or made me feel like I had to choose baseball just because he did. If I'd wanted to play soccer in college, he would have supported me fully. He took me to the batting cages and played catch with me all the time, but he never pushed. The biggest things my dad taught me were to work hard, have fun, and always, always, always be early. (He also taught me how to throw a mean knuckle curve ball!)

In pro ball, my most impactful coach was Gary DiSarcina. He was a former big leaguer who knew the Xs and Os, but that's not why he had such an impact. He treated me like a friend, not a subordinate. DiSarcina believed in doing things your own way. He'd tweak mechanics here and there, but mostly let us play our game. He only had 2, maybe 3 offensive signs from the third base box. If you could run, steal—just be smart. If you could bunt for a hit, do it—just be smart. Those freedoms made me love competing for him every night.

When you started experiencing symptoms in early 2010, right as you were peaking as a top prospect—what kept you mentally strong through the diagnosis and first surgery?

I guess I was always just really driven, and through the whole process my mindset didn't shift at all. I wanted to make it to the Big Leagues at Fenway Park. I was also still very young, so I think I didn't fully understand what was going on or what the outcome could be. So maybe I was naïve about it, but I just wanted to move past it and heal and get back on track to being the Boston Red Sox center fielder.

The setback leading to a second surgery in 2012—how did you find the strength to go through it again? What did that teach you about resilience that you now share with players you coach?

Leading up to the second surgery was the biggest blow I took. I finally realized that playing baseball wasn't in the cards anymore. I leaned heavily on my support system—close family and friends came to Arizona for that surgery and made it easier. After I woke up, I received letters from people around the world offering support. Seeing friends like Will Middlebrooks and Josh Reddick having success in the major leagues brought a smile to my face.

As a coach now, I tell my players that baseball is going to end for everyone at some point. Thirty years from now I don't care to be remembered for my Single-A statistics—I want to be remembered by that little kid in the stands that I signed an autograph for. It's great to be remembered for what you did, but what matters more is being remembered for who you are. Your character cannot be taken away from you.

Announcing your retirement at 22 years old, when baseball had been your entire identity—how did you process that? Who or what helped you through it?

My friends and family helped me a ton through that. They knew me my whole life and knew how much baseball mattered to me and how difficult this was. So I really leaned on them a lot during that time and in finally making the decision to retire.

In addition, my Red Sox teammates made it a lot easier. They knew who I was as a player before my surgeries, and although they were incredibly sad that my career was over, they offered me tons of support, and, to this day, I'm still good friends with a lot of my former teammates or front office members.

The Red Sox front office was literally the reason I graduated from Northeastern University in 2024. It is very rare for an organization to support a former athlete to graduate college who had been retired for as long as I had. So I'm very grateful for them and their support since day one.

You're now coaching at UMass Dartmouth and in youth baseball. What made you want to get back into the game this way? What does coaching give you?

Coaching just reminds me how much I love this game. I love giving back and giving knowledge to players, both at the collegiate level and the younger players. I could talk all day about the intricacies of mechanics and things like that, but I believe I have a lot of knowledge based on my experience about more than just baseball to give my players. Like I said earlier, how you are off of the field matters most, and I try to embody that as a coach, making players feel like I am more than just a baseball coach to them.

Having experienced both the highest highs (top 25 MLB prospect) and the crushing loss of your career, how does that perspective change the way you coach young players? What do you emphasize that other coaches might miss?

I try to explain that baseball is more than just the game itself—it takes so much more than physical talent to be good. I try to instill in them what was instilled in me: work hard, have fun, and be a good person. I learned the importance of having good, supportive people in your life, so I try to be that for them. Someone they can trust and talk to, both on and off the field.

Your baseball career was taken from you at 22. For parents whose kids' entire identity is wrapped up in being 'the baseball player,' what do you wish they understood about helping their child build something bigger than the game itself?

I always want parents to think about their kids as more than 'the baseball player.' Not just because it could be taken from them at any moment like it was for me, but because no matter who you are, you're always more than one thing. You're more than one identity. Even if you love something so much and you're incredibly talented, it's important to also recognize you are a student, a son, a brother, and so on.

You're coaching youth players now. When you see parents obsessing over results at 12, 13, 14 years old—what do you tell them? What actually matters at those ages if the goal is developing a player who can compete at the highest levels?

At that age, it's so much more important for kids to be playing because they love it. They need to show up every day because they enjoy it and they want to be there. Of course, it's eye-catching to see guys making millions of dollars playing the game they love. But at that age, it's about having fun, learning the game, and developing the right way, which is what our Ocean State Makos program preaches.

Statistics are great, but overall the big questions are: did you have fun? Did you improve in areas you wanted to improve in?

How did you stay coachable when you were succeeding at all levels? What do you tell talented kids about that now?

Even when I was at the top of my game, I fully understood that there were, and always will be, ways to get better. Whether you're in the MLB or T-Ball just learning the game, there's always more for you to learn.

A phrase that was said to me when I was probably 10 years old in YMCA Basketball by my coach, Joe Occhi, is "practice doesn't make perfect, practice makes permanent." I kind of lived by that and I realized if I wanted to get to a place where something was permanent for me, the key was repetition and doing things over and over again the right way.

If you could go back and tell your 18-year-old self something on draft day 2008, knowing everything that would happen—what would it be? What do you wish you'd known then that you know now?

I think I would tell myself to just do what you can to be happy. And understand that baseball is a game, and there is so much more to life than your job or being successful at whatever you're doing. I'm fortunate enough now to have a wife and 2 daughters who are everything to me.

I would tell myself that regardless of what happens, there is more to life than just being a good baseball player.

Ryan Westmoreland's story hits different.

A scout once compared him to Mickey Mantle.

He had everything. The talent. The love for the game. A top prospect ahead of Mike Trout, Freddie Freeman, Aroldis Chapman, and Zack Wheeler. All-Stars & maybe a couple of future Hall of Famers.

That's how good Ryan was. He was a generational talent.

And then it was gone. Two brain surgeries. Retirement at 22.

But here's what struck me most:

"I don't care to be remembered for my Single-A statistics. I want to be remembered by that little kid in the stands that I signed an autograph for. Your character cannot be taken away from you."

That's wisdom you only get from loss.

As parents, we obsess over scholarships, recruiting rankings, showcase tournaments. We want our kids to be the best player on the field. But Ryan's story forces the question we avoid:

What happens when baseball ends?

For Ryan, it ended at 22. For your son, it might end in high school. For a lucky few, college. For an even smaller few, pro ball.

But it ends. Always.

Ryan's still standing tall because of what he built beyond baseball. His family. His wife and two daughters. The Red Sox organization that supported him through retirement and helped him graduate from Northeastern in 2024. The teammates who stayed in touch. The character he carried with him when the uniform came off.

Your kid is more than "the baseball player."

Ryan said it: "Even if you love something so much and you're incredibly talented, you are a student, a son, a brother."

He loved baseball. He was incredibly talented. And it was still taken from him.

But he's okay, because baseball was what he did, not who he was.

The game ends. Character doesn't.

So let them play multiple sports. Let them love it for the right reasons. Let them build something bigger than a batting average.

To your son, baseball is life. But it will end.

And what's left is who they became along the way.

We need more people like Ryan. People who understand that their job isn't just teaching fundamentals, it's preparing young men for something bigger than baseball.

Ryan lost baseball at 22. But he never lost himself.

"I would like to stress the importance of a few things now being a college baseball coach. The first thing is to be a good person off of the field (college coaches put a lot of value into what kids are like off of the field).

The second is that I think a lot of players and parents have their eyes set solely on D1 schools. A common misconception is that D3 college baseball is "13th grade" or not good baseball. There is very good talented baseball at all levels in college. It's incredibly rare to play baseball after college, so I really wish more people would understand that and not put so much weight in the "D1 or bust" mentality."

Help me keep more kids in the game. If you found this helpful, please forward it to another parent or coach.

Thanks for being here. See you next week Inside the Dugout.

-Coach Steve-

Steve Holmes
Founder, Inside the Dugout
2006 MLB Draft | All-American | Youth Coach | Dad