Tabbed as the school’s newest athletic director in March of 2024, Jason Maxwell has now been at Ensworth (TN) High School for more than 20 years, serving first as the founding head baseball coach and director of middle school admissions.
Ensworth’s baseball program has risen to national prominence under Maxwell, sending players to schools such as West Point, Duke, Notre Dame, Georgia Tech, Vanderbilt, Belmont, Xavier, Tennessee and Lipscomb.
Coach ‘Max’ held leadership roles in the Tennessee Baseball Coaches Association and currently serves as the High School Chair on the American Baseball Coaches Association Executive Committee. He’s also suited up for Team USA as an assistant for the 2016 15U National Team and manager for the 2018 15U National Team that captured gold in the WBSC World Championship in Panama. Maxwell also managed the 2021 18U National Team.
Additionally he was named the USA Baseball Developmental Coach of the Year in 2018, won the Tennessee Baseball Coaches Association DII-AA Sectional Coach of the Year (2019), and coached in the MLB/USA Baseball High School All-American Game (2021).
Maxwell was a three-sport star at nearby Marshall County High School. After a highly successful career at Middle Tennessee State, he was picked by the Chicago Cubs in the 1993 MLB Draft. He played in pro ball for a dozen years and reached the major league level with both the Cubs and the Minnesota Twins.
Inside Pitch: When did you know you wanted to coach?
Jason Maxwell: It’s something that I’ve always had the ambition to do, especially at such a prestigious school like Ensworth. Towards the end of my playing career, I knew I wanted to help kids. I was an education major and I love all sports—not just baseball—so being able to develop an inclusive culture, impact kids, share my experiences and some knowledge that I’ve gained over the years…all that has been very fulfilling.
IP: What was it like being the founding coach of the program?
JM: When I started here, we had 13 players and maybe two of them had played before, so we had to really coach them up. Honestly? I thought I would do it for a couple years and open up a facility and train kids from there. But once we got this up and running, I knew I wasn’t going to go anywhere if I could help it. Developing relationships with these kids, their families, the whole community—it becomes a real part of your life, starting with the kids we began the program with more than 20 years ago.
IP: How are you able to handle the parent dynamic as a former big leaguer?
JM: You have to be up front with them. You tell them they’re not always going to like your decisions. We have been consistent with that tone and have gotten great buy-in, and for some lucky reason, things have run really smoothly, even though not all of our kids are going to play in college.
I make sure everybody understands their role, and then we coach them on how they can be ready to go when their name is called. And I dedicate myself to just giving them the experience of a lifetime while they’re in our program. It just takes effort!
IP: Who did that for you as a player?
JM: I think I took something from every single one of my coaches. Steve Peterson at MTSU was so good to me, and Tom Kelly, my manager with the Twins. He was just so fair, he never judged where you got drafted or what others said or thought about you as a prospect or whatever. If you did things the right way, you were going to get opportunities playing for TK. There are so many things he did as a manager that I still try to emulate today.
IP: Speaking of pro ball, I gotta ask—do you tell people you got drafted in the 74th round?
JM: People think I’m joking because they know those rounds don’t exist anymore! But I did get drafted in the 74th round, and I wound up in Huntington, West Virginia, and the manager said “I don’t know what we’re gonna do with you. I don’t know how much playing time you’re gonna get.”
I finally got to play one day in front of some of our front office brass—Syd Thrift was one of them. And I struck out three times. Syd’s walking up to me after the game and I’m like, “it’s over, this is it.” I can remember having the most empty feeling, until Syd starting talking about how much he liked my swing! They saw something I didn’t see, they gave me the confidence to keep pushing. I knew I could play, I had a great college career, but you never stop needing that affirmation as a player.
IP: Speaking of support, how do you go about dividing your professional life from life at home?
JM: You have to prioritize. And no matter what—for me—my family comes first. My wife is amazing, so supporting in everything I do. None of it’s possible without her.
I have two sons that kind of grew up in this life, but they know for them I’m just dad. We rarely talk about all the ins and outs of what’s going on here when I’m at home. Now when I go to other places, my youngest son is always saying he doesn't want to come because of “how long we have to stay afterwards!” But in all seriousness, their support means the world to me, and it really enables me to do what I do everyday.
IP: How’d you go from a 38-error season at shortstop to a 16-error season the very next year?
JM: That first year I was in the Florida State League, that was a real eye-opener to me. I swear everyone in that league was really good, especially that class of shortstops: Jeter, Nomar, Rey Ordonez, Edgar Renteria—those were some dudes! And I was trying to be as good as them and I just wasn’t; I wasn’t playing like myself. So that offseason I took ground balls every day, and I mean every single day. My confidence just grew and grew, until I finally saw my name in one of those Baseball America top prospect lists as one of the best defensive shortstops in the Florida State League.
But in terms of the help I got, when I got to big league camp, Ryne Sandberg and Shawon Dunston were tremendous, giving me advice on a daily basis. I had a manager, Dave Trembley, who named me “team captain” one year—that’s affirmation. You take the bits and pieces that give you confidence like that, and you carry them with you all along the way.
IP: And you have some real stories to tell as a coach now…
JM: It’s easy because I can tell these kids, “there’s literally no way you guys are gonna make as many errors as I did; it’s not possible!” But I do use those moments as ways to build the relationships with my players.
IP: And on the other hand, do you ever have to say, “Please just trust me—I played in the big leagues!” Or do they just go with it?
JM: Sometimes you have to drop the card, but when I'm doing it, I’m teaching, maybe trying to get their attention. I’ll say, “you know when I was in the big leagues and this is what so and so told me and it really helped me out, and I think it can help you out too.”
IP: That kind of credibility helps a lot with college coaches and pro scouts too?
JM: I don’t take it for granted when college coaches call me and trust my word. That is a big deal. But my players know I’m going to be honest with them. I tell my guys to stay off of social media all the time. You don’t have to post every hit. But I’ll help the kids and families try to decide on travel teams, showcases, some of my former players are asking about the portal; I don’t know where that’s going, which is a little scary.
IP: What are those conversations like nowadays when it comes to diversity in baseball?
JM: To watch it grow has been phenomenal. It can happen, right? At the last ABCA Convention, a young kid came up and talked about how much he admired me and Kerrick Jackson, who I was with at the time. That was so humbling and so great to hear. But you’re starting to see more kids that look like us that are playing baseball, getting into coaching, and committing to improving the diversity in baseball.
Now, is it where we want it to be? Absolutely not. But I think it’s coming, and the kids are leading the way. Guys like Termarr Johnson, Druw Jones, Elijah Green, R.J Austin, and so many others have so many kids their age looking up to them. It’s amazing to see the impact that they’ve had on the youth, through just playing the game.