Image credit: Trey Wilson Broadcasting Flying Squirrels Game
There’s a variety of paths to get to a professional baseball broadcast booth. Trey Wilson’s started by unloading trucks and stocking shelves at K-Mart.
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Like many other teenagers, Wilson wasn’t quite sure what he wanted to do with his life. A tall,
hard-throwing right-hander from the Hampton Roads area in Virginia, Wilson attempted to
continue playing baseball post-high school at Bluefield University (then-Bluefield College) but
injuries and poor academic performance cost him both his spot on the baseball team and at the
Wilson returned home and picked up the K-Mart gig, but quickly realized a life of minimum
wage retail work wasn’t for him. He moved back to Bluefield, and went to work earning his way
into a second chance at school. It took time, but Bluefield decided a re-dedicated Wilson was
worth having back on campus as a student.
“I was a pretty strong student that second run,” said Wilson.
The strong student needed a path for his studies. Originally wanting to work in music, Wilson
instead went with a different kind of audio.
“I wanted to stick with sports, so I got involved with the athletic department there at the college,
and they gave me some great opportunities that I wouldn’t have gotten if I’d been at a bigger
school,” said Wilson. “They needed somebody to call a volleyball match, I signed up, I did it, I
was absolutely awful—terrible, terrible job, I’d never done play-by-play before, but I stuck with
it and kept doing some stuff as a student.”
Wilson eventually parlayed working in calling Bluefield College athletics into a full-time job
with the sports information department. Throughout his time at school he was able to call
baseball, men’s basketball, and their brand new football program on the local flagship radio
Wilson had also been writing online covering Blue Jays prospects, and when Toronto took over
the Appalachian League affiliate in Bluefield, Wilson got his first step into Minor League
His first step didn’t mean stability, or livable wages—the MiLB broadcaster grind can resemble
the MiLB player grind, as Wilson found that advancement took time, and a lot of failure.
“I applied for fifty jobs before the 2014 season—I came in second a lot,” said Wilson.
He eventually moved on from Bluefield for an unpaid position with then Low-A Lansing, but
one that allowed him to call all 140 games, home and road. He’d saved up a bit of money from
working at a seafood restaurant and had a host family, but without getting per diem on the road
or a paycheck from the team, meals were an adventure.
“There was this McDonald’s on my drive into the stadium every day that I knew I could get a
McChicken, a small fry, and a large sweet tea for like four dollars and some change, and that
could get me through to game time,” said Wilson.
During his time in Lansing, and eventually for Double-A Altoona in the Pirates organization,
Wilson worked to set himself apart, offering more than just a voice in the booth. His resume of
usefulness for MiLB clubs runs deep, as he’s done work with marketing, running websites, video
work, HTML coding, and any other odd job he can find.
“I think what I lacked as a play-by-play broadcaster early on, I covered a lot of ground getting
opportunities because of the off-the-air stuff, and I could kind of handle myself on the air,” said
During the 2018 offseason, Wilson was named the voice of his home state Richmond Flying
Squirrels, and serves as the Director of Communications and Broadcasting. While like anyone
else, Wilson dreams of one day calling a big league game, true to his nature he’s involved in
every aspect of growing the Flying Squirrel brand locally—something that looks to be providing
a lifetime of fulfilment.
“This job has enough challenge to it, that I don’t think will ever stop, that I could be here and be
happy, and be the voice of one of the most visible sports brands at least in Virginia, but maybe
beyond that,” said Wilson. “If I’m here for the rest of my career, that’s awesome.”
On the latest episode of ‘From Phenom to the Farm’ Richmond Flying Squirrels broadcaster
Trey Wilson joins to walk through his journey through MiLB from the play-by-play booth.