This story is part of our ongoing “First Steps” series, where we share extraordinary stories of men who transformed their bodies, minds, and lives with a focus on the first steps it took them to get there (because, after all, nothing can change without a first step!). Read all of the stories here.
Every fan of Major League Baseball knows the name Adam Wainwright. After making a major splash as the St. Louis Cardinals closer as a rookie during the 2006 playoffs—helping them secure a World Series championship—the then-25-year-old went on to play the next 17 years of his career as a starting pitcher for the Cardinals, winning two Gold Gloves, leading the league in wins twice, and earning three selections to the National League All Star team.
During his final season with the Cardinals in 2023, Wainwright surprised the baseball world when he belted out a rousing rendition of the national anthem before a game. This proved to be a sign of things to come for the next phase of his life, as Wainwright has since made a huge career change. In the time since his baseball career ended, Wainwright has played at Nashville’s country music institution the Grand Ole Opry twice, and released his debut album, Hey Y’all, in April 2024.
Below, Wainwright, who now lives in St. Simons Island, Georgia, explains how he executed his career pivot from baseball star to country singer.
I ALWAYS BROUGHT my guitar on the road and to spring training. In 2017, I was at [former Cardinals teammate] Matt Holliday’s spring training house down in Florida. He would always say, “Hey, Waino, bring your guitar over,” and we would have eight or nine players over there, and people would be giving requests, and I’d play and sing. We had these little mini concerts.
That one particular day, though, Holliday’s neighbor’s dad—a guy named Gary Baker—was there. Gary wrote a song called “I Swear,” which everybody in the world has heard before, and wrote seven other number one hits. He’s also produced for the Backstreet Boys, Jessica Simpson, 98 degrees—all of those big late ‘90s boy bands and pop bands. I got done playing, and he walked up to me and said, “You know, you’re not bad. We should make some music together.” Once I found out who he was, I thought, you know what? I’m up for anything. He asked me, “Are you writing songs, or are you just playing covers?” I told him, “I write some, occasionally, but I have no idea what I’m doing. I can tell you how to throw a curveball, but I don’t know if I’m gifted at songwriting. But I do like to do it.” He told me to email him when I wrote songs, and he would help me work them into something bigger and better.
Wainwright pitching for the St. Louis Cardinals.
It took me about a year to build up the nerve to send him a couple songs; I wrote one called “One Day They Won’t” that I sent to him. I’ve got five kids, and in the varying stages of them growing up, at some point I started to realize that they don’t always get up in your lap and want to watch a movie and stuff. The song was all about that. I sent it to him, and he called me immediately. He said, “Now that is a good country song. Let’s do more of that.” We started writing a few songs together. If you asked him and me at the time, it was just to help me have something cool for around the campfire, or sitting in the living room with friends or family. As we got more and more involved with it, Gary just kept saying, “This might be a bigger, cooler project than I thought it was. What do you think about recording an album?” I was like, “Well, that sounds amazing, but am I any good?” He was like, “Dude, this is really good stuff, man. The world needs to hear this stuff.”
That’s how it’s started, and we’ve taken off from there. I don’t know how many hundreds of songs since then we’ve written, but I finished one last night—I’m having fun with it. The songwriting and creating process is my favorite part. I try to play music for at least 20 minutes a day. I do at least one singing lesson a week, and one guitar lesson a week. Usually, right after I get my youngest two to bed, at about 8:30, I go to the garage, which is almost always my recording studio. I sit in the chair on my Jon Boat; it’s somewhere I know I can get loud, and not mess anything up. My recording booth is my iPhone. I’ll record something, or write something, and send it to Gary. I’ll start going up to Nashville and getting some recording sessions in during the next couple of months, probably for the next album.
Having the right people on board is key. But the main thing is not being afraid to put yourself out there. When I decided to make the jump into the music world, I had to completely buy into that. I was a baseball player, but I’m really taking this [music] seriously and I want to be taken seriously. I don’t want to be a guy who they say, “Oh yeah, he was a baseball player and every now and then he plays a couple of songs.” I want to be the guy who they say, “We went to his concert, and they put on a great show. That was a really fun environment. He was doing great, and the band was awesome.” If it’s something you really want to do, you have to believe wholeheartedly in it and go for it.
Wainwright performing at the Grand Ole Opry in Nashville.
Anything you want to be good at, you have to work at, whether that’s baseball or music or marriage or parenting. I have a voice lesson today because there’s some top-end range that I haven’t unlocked yet. I know it’s inside, but I haven’t been able to get there yet. Next week, I start back with my guitar lessons. I have a great teacher out of Muscle Shoals, Alabama, and I’m trying to learn the craft. I just learned the number system, which in music is super cool and unlocks a whole lot of different ways to play songs. I’m still trying to be locked in on my family time because I’ve missed so much [during my baseball career], but when I do have those spare moments, I would like to get better at the things musically that I’m trying to accomplish.
I don’t measure success in albums sold. I measure success in the amount of fun we’re having. I measure success in the music we create. If I really believe it’s good and the people who I work with believe it’s good and when people come to the shows are having a great time, then that’s what I truly consider success.
