Ben Simon’s dual path from player development to player representation
BY JIMMY OSWALD
Ben Simon’s day begins at 8 a.m. in Orlando, watching a player from New Jersey take the diamond. After the game, he drives six hours to Atlanta to see one of his pitchers perform, then wakes up the next morning for a nearly seven-hour drive back to Florida in Lakeland to watch two pros throw at 11 a.m. — then heads an hour north to catch a high school game at 1:45 p.m.
“And that’s normal,” Simon says. “Eight to 10 hours is a normal day.”
Simon, a graduate of Orange High School who lives in Moreland Hills, is a Major League Baseball Players Association-certified agent and the founder of two baseball enterprises: Simon Sports, the agency he’s run since 2017, and Prospect Performance Academy, a development facility at 9061 State Route 14 in Streetsboro that works with players from middle school through the college level.
The combination is unusual. Most people in baseball pick a lane. Simon built a career out of straddling both.
“What I like is being a voice and an advocate for players that have never had one,” he says. “I like helping players in ways they can’t help themselves.”
From the mound to the business side
Simon, 31, grew up in Boston as a Red Sox fan before moving to Cleveland, where he played for Orange High School (class of 2013) and later pitched at Case Western Reserve University. He stopped after his sophomore year — not because he lost interest in baseball, but because he found something he was better at.
“I looked in the mirror and said I have to stop doing something I’m not all that good at and start doing something people have told me I have a chance to be pretty good at,” he says.
He had already been training pitchers since he was 19. When he told college coaches he was thinking about representation, they encouraged him — what he was doing with players wasn’t so different from what agents do. He founded Simon Sports at 22, and the pitchers he’d trained early on helped him sign players a young agent wouldn’t typically land.
Building a pipeline
Simon said Prospect Performance Academy has had more than 15 players drafted into Major League Baseball since 2019. He declined to name specific clients, but according to Cleveland.com, that group includes AJ Blubaugh, a PPA alum drafted by the Houston Astros in the seventh round in 2022, who has appeared in 11 major league games, going 3-1 with a 1.69 ERA out of the bullpen and is on the active roster for 2026, and JB Middleton, a second-round pick by the Colorado Rockies in 2025. Eleven of Simon Sports’ clients are ranked among the top 30 prospects in their respective organizations.
Jake Miller, a pitcher in the Detroit Tigers’ system who was drafted in the eighth round in 2022, works on his game during the offseason at Prospect Performance Academy in Streetsboro.
Photo courtesy of Ben Simon
Simon traces much of that success to a simple philosophy about margins.
Connor McGough, a Cuyahoga Valley Christian Academy High School senior who has committed to Davidson College in North Carolina, takes a few swings while practicing at Prospect Performance Academy in Streetsboro.
Photo courtesy of Ben Simon
“The difference between elite and average in this game is so small,” he says. “If you take a pitcher throwing strikes 60% of the time and get him to throw one more strike out of 25 pitches, he probably becomes an average to above-average major leaguer. If you can help a guy get a little better, it pays off in a massive dividend.”
That same directness shapes how PPA operates. Simon says he tells every player who walks in — whether a 13-year-old or a big leaguer — that he’ll train them and talk to them the same way.
“I have the same standard for every player in the building,” he says. “The cool thing is there are kids who showed up here as average high school players and are now the major league prospects they used to look up to.”