How Piedmont’s Jack Chester turned the end of his playing days into a new career

Former two-sport star at PHS now giving hitting, pitching lessons in Oklahoma City

2027
Jack Chester gives a group lesson to aspiring youth baseball players.

By Blake Colston
Sports Editor

A former Piedmont baseball star is following his passion for the game away off the diamond as he mentors the next generation of potential stars.

Rated as one of Oklahoma’s top prep players in the class of 2019, Piedmont High School alum Jack Chester signed with Murray State College in Tishomingo after a stellar prep career at PHS. A 6-foot-5, 190-pound right-hander with a fastball in the low 90s, Chester had a legitimate chance to pursue a professional career.

But after two years at Murray State, a string of arm injuries forced Chester to retire from baseball.

“I loved the game and wanted to be around it,” he said. “I just realized it probably wasn’t going to be as a player anymore.”

So, Chester became an instructor at PitchingWRX in Edmond while continuing to train for a potential long shot opportunity to play professional baseball.

When his window to play pro ball closed, Chester decided to follow his heart. Through mutual connections, Chester found a position at D-Bat, where he now hosts individual lessons inside the organization’s 50,000 square-foot baseball and softball training facility located in Oklahoma City at 801 NW 122nd St.

Chester gives hitting and pitching lessons to players from across the metro area with a plan he personally designs for each of his students.

“The big thing is, I care. That’s where it starts,” he said.  “There are plenty of people out there with baseball knowledge that can give you cookie-cutter instructions. But I care about all the kids I teach and want them all to develop.”

Chester can tailor his 30-minute or hour-long sessions to all ages and ability levels, from beginners to college players.

“Yesterday, I coached a kid who was 12-years-old and was attempting to play for the first time. I could obviously see that he was uncomfortable,” he said. “But we had fun.”

With a resume like Chester’s, he could probably have found a job as a high school assistant coach, but he prefers to focus on individual and small group coaching.

“Doing this, you don’t feel like, ‘Oh, I wish I had 20 more minutes with so-and-so,” he said. “You get to focus an hour at a time with each kid and I feel like you can grow by leaps and bounds that way as opposed to coaching a ton of kids at one time.”

Former Piedmont and Murray State College pitcher Jack Chester is now available to give one-on-one pitching lessons.

Chester hopes this venture can potentially become his livelihood, but he’s not motivated by the money.

“When something really, really resonates with a kid and the lightbulb comes on, that’s my favorite part,” Chester said.

Contact D-BAT at (405) 694-4448 for more information about individual lessons and pricing.