How’s it going everyone my name is Riley Wilson, a left-handed pitcher in the Philadelphia Phillies organization. I signed as an undrafted free agent in 2019 after spending five unforgettable years at the University of Virginia. My road into professional baseball is not as linear as most others, but I think it makes for an interesting story. I told Connor when he asked me if I’d want to put a piece together that I could make this into a book… but I’ll try to keep things as concise as possible and get to the point while still depicting some inside details of my baseball journey that most people don’t know.
To give a little backstory of my baseball bloodlines and what I grew up around, my dad was drafted by the Padres in 1979 and played three seasons in their organization before having major surgery on both ankles… at the same time. I didn’t even know that was medically feasible, but that unfortunately cut his professional career short. My older brother, Tyler, also played at the University of Virginia and had a way more successful career than me. All-American, All-ACC, never got a bad grade; you name it, he probably did it. After his four years in Charlottesville he was drafted in the 10thround by the Orioles in 2011 and made his Major League debut in 2015. He pitched in the show for parts of three seasons with the O’s before heading to South Korea in 2018 to pitch for the LG Twins of the KBO, which is where he still is. He’s a freakin’ stud, my dad was a stud, so ever since I picked up a ball I viewed professional baseball, more specifically the big leagues, as my goal. I wanted to be like them, they were and still are the people I look up to. With that being said, let’s get into my baseball journey, starting with my arrival to UVa.
It was August 2014 and I was beginning my 1st year playing at my dream school; a school that had just come off of a College World Series finals appearance, sounds ideal right? Let me tell you, I don’t think I could’ve been more mentally lost if I tried. I was pitching and hitting at the time, not doing either very well. There were points in time where you probably could’ve asked me what my name was and I wouldn’t have been able to answer that correctly… I was a mess. I never really had to fend for my self in the time leading up to college, which made the transition into college pretty tough for me. I was very much a “homebody” growing up, and still am now. Being in a new social atmosphere, making new friends and getting a million hours of homework slapped on me per week definitely contributed to me feeling perpetually overwhelmed. Compound that with competing everyday at practice with some of the best players in the country, I really felt in over my head.
Fast-forward a few months and I was finally starting to somewhat grab ahold of myself and slow the game down to be able to understand what was going on around me. Fall ball had just ended and we went into individual training sessions with coaches (BP, flat-grounds, defensive work, etc.) and at that time I had taken a few weeks off from pitching to focus solely on hitting. I will forever remember Monday, October 6th, 2014 as the day my baseball career changed. I was swinging in one of my individual sessions when I check-swung and heard a pop in my left shoulder (Lesson to that is never check swing… I guess). I knew something wasn’t right, but I didn’t know exactly what it was. I tried to swing again and it felt like someone dropped a boulder on my shoulder so I went in and saw our trainer. He ran me through some surface level tests and initially came to the conclusion that it was a strain, nothing too crazy. The plan was to rehab for a few weeks and go back playing as normal. Rehab came and went, and when I returned to throwing I could barely make a ninety-foot throw. An MRI soon followed, which revealed a pretty severe tear to my labrum and biceps tendon, which would require surgery. This is obviously the last thing any athlete wants to hear, especially a throwing athlete. I was sent down to Pensacola, Florida to be operated on by Dr. James Andrews, who has seemingly done every surgery ever. I did a bunch of research leading up to the surgery and found a stat that around 50% of throwing athletes who sustain the injury I had return to playing their sport. So to be in the hands of someone like Dr. Andrews certainly made me more hopeful that I would end up on the good side of that 50%. The surgery went to plan, and Dr. Andrews is absolutely first-class. The long road back had officially started.
For the first six or seven months post-surgery I had two rehab sessions every day, both of which being about an hour long. This was one of the most challenging periods of my entire life because I was forced to sit and watch the game I love for the first time in my life, all the while knowing that it was going to be a long, long time before I would be able to rejoin my teammates. There were plenty of long days, and plenty of days that I simply didn’t want to go through it anymore and thought about giving up, but my teammates and trainers helped me get through the tribulations. Oh, and a trip to the College World Series culminating in a National Championship certainly threw a few logs on the motivational fire to keep trucking (sorry I had to mention that in here somewhere).
After rehabbing myself up for 10-ish months I finally was able to get back on the mound for a bullpen, my first since the injury. About eight or nine of my teammates sat on the bench behind the bullpen mound to see what I was going to look like, because most of them had never seen me throw in my fifteen or so months of being at Virginia. I warmed up and everything felt great, talk about adrenaline. About two minutes later all of that joy of being back on the mound evaporated. After my second pitch off of the mound, I got that same feeling of someone dropping a boulder on my arm that I had initially felt. Pull the plug, back to square one. I shed tears in my locker that day, because that was the first time that I genuinely felt like I would never play baseball again. All of the rehab, all of the weeks and months put into building myself up, all undone in two pitches. I owe the world to our trainer Brain McGuire (the best in the business) for never abandoning me and getting me back on track mentally to attack this rehab for a second time. I was completely shut down from throwing for the next six months and went back to the plan of two grueling rehab sessions per day. At this point it was clear I was going to miss a second full season due to this injury, at which point it would’ve been easy for the coaching staff to turn me loose. I will forever be grateful for them sticking by my side and breathing life into my baseball dream.
I could keep going into detail about rehab and all of that but I’ll move the story along here and get away from the gloomy stuff. After twenty-three months and two full seasons away from the game spent rehabbing, I made my first collegiate appearance against Rutgers. The score to the game was like 18-3 or something ridiculous like that when I came in during the 9th inning, but to me it felt like the World Series. I finished the game and kept myself in one piece, and was met with an excitement from my teammates that I’ll remember for the rest of my life. Throughout my time at UVa I was used as a high appearance left-on-left reliever, which is certainly not the most glamorous role, but a role that I learned quickly to love. Coming into high leverage situations is what baseball is all about; who is going to emerge as mentally tougher? Virginia certainly armed me with a mental toughness that enabled me to feel comfortable in those uncomfortable situations. Everything we did, from conditioning in the fall to our incredibly high intensity practices were all to prepare us for the times when we would inevitably face adversity. The University of Virginia is a challenging program to play in, no question, but everything we did was for a reason, and I will always be thankful for my five years as a Cavalier.
Moving forward to mid-2019, my fifth year concluded as graduation came and went with me receiving a master’s degree from the University of Virginia (something I never thought I’d say). I had a good college career but the opportunities that would arise for my baseball career were still to be seen. The draft came and passed, and my name was not one of the 1,217 called. Obviously I was devastated, but I knew what I was capable of and wanted to continue playing. A full day passed after the draft’s conclusion without hearing anything, but the following day my agent called to inform me that there was an independent league team in Kansas City that had inquired and wanted to sign me. I remember my emotions being extremely conflicted, because I was over the moon about having the opportunity to continue playing and to become a professional, but also having the self-belief that I could get big league hitters out and just hoping the phone would ring with it being a Major League club wanting to give me a shot. I slept on my thoughts and the next day I still hadn’t heard from any clubs so I decided to move forward with the Indy ball opportunity. Again I knew deep down I could get hitters out, I just needed a shot. This was my shot to play in the big leagues, albeit a non-conventional and extremely indirect shot, but a shot nonetheless. I called the GM of the team and he informed me that he was actually offering me an opportunity to drive out to throw a bullpen in front of their people the next day, and potentially sign me after that. Granted this would have been a nineteen-hour drive on just twenty-four hours of notice for me to get there to merely throw a bullpen. I remember sitting in the floor of my brother’s townhome and the thought of “I have two degrees from the University of Virginia, should I just move on with my life and find an office job or something?” creeping in my head. But I just couldn’t pull myself to actually think that way. I love baseball with every fiber of my being; I always have, so I was prepared to make the drive and take the chance. I was in the process of calling the GM of the Indy ball team to let him know I’d be there the next day when I felt my phone buzz up against my ear because I was getting a call. It was an area scout from the Phillies whom I had talked to prior to the draft a few times. I knew this was it. I picked up right away and I’m sure the excitement in my voice was evident, because I was losing it internally. He offered me the chance to become a Phillie and I accepted it without an ounce of hesitation. Those conflicting emotions were gone, it was pure jubilation as I realized my dream of playing professional baseball were coming to fruition for real this time.
As for my professional career to this point, it’s still very much in its infancy, so I can’t go too in depth here. I only pitched 21.2 innings this summer after signing, but there was so much information that I was able to gather during that short span. Professional hitters are certainly different than college hitters, so there were constant adjustments going on during the season. This COVID-19 pandemic certainly does no favors for minor leaguers, especially undrafted free agents, but there are some things that are merely out of our control. I can only continue to put my head down and be as ready as possible for when the bell tolls and we can resume baseball. Whenever that day comes, I know I’ll be more than ready.
As I said previously, my baseball career has certainly been far from traditional, but there’s nothing I’ve done along the way that I regret. Everything we do in life shapes us to be who we currently are. It’s an event like a major injury that temporarily takes our sport away from us that really helps to gain perspective of how lucky we are to play in the first place. It’s the greatest game in the world and I am so grateful for everywhere this beautiful sport has taken me and continues to take me. From Richmond, Virginia to Omaha, Nebraska and now to professional baseball. This game has given me so much and allowed me to create so many connections, I will forever be grateful for the game of baseball, and can’t wait to progress upon this journey even further.
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