“Smiley J” Jay Jackson was born and raised in Greenville , South Carolina. He also attended local Furman University. On the field, his performance at Furman caught the attention of scouts. Off the field, philosophy caught his attention.
Jay Jackson was drafted in the ninth round by the Chicago Cubs in the 2008 MLB draft. “I went a lot lower than I expected, actually,” remembers Jackson. “All the workouts I had done previously and this what I had heard from scouts and different teams before the draft, I’d actually went a lot lower than I thought. From what I was projected to go to, I think, I believe that year I was projected in like the first like four rounds. And so me going into the ninth round was kind of late.”
The Cubs seemed to respect Jay as a top four round pick, however. He quickly climbed three rungs of the minor league ladder in his shortened professional debut season and again in his sophomore season in 2009. He’d find it difficult to take that final step to the MLB level, however, spending parts of 6 seasons in AAA before finally receiving the call with the San Diego Padres near the end of the 2015 season.
Jackson says, “I wouldn’t say I stalled out at AAA, but I got there and then the PCL kind of takes a hold of you. I kind of got down on myself a little bit going through a little funk too that didn’t help with where I was at. I think my second and third year, I just got into like, not bored, but I got just like down being stuck in AAA for a little bit. Maybe a change of scenery would have been nice, but you you just kind of work through it and luckily I got the chance and opportunity to go somewhere else after those days and you know, my career kept going on.”
Jay would spend parts of seven seasons with six major league teams and an additional three seasons pitching in Japan. He signed with the Bravos de Leon of the Mexican League for the 2025 season before deciding to retire prior to the beginning of the season.
On his decision to retire, Jay says “I was actually rehabbing. I was going to be cleared to play again, but I ended up getting a PRP in my left knee and my right shoulder and I actually didn’t get cleared from that till mid-January. I got back from that finally, I did a couple bullpens and just I realized that me going to Mexico, I didn’t want to go down there and not give my all and not enjoy baseball the way I wanted to so it was more I wanted them to go give the spot to somebody that was going to go down there and be really hungry. [Also,] I feel like the pathway for me going from Mexico to the big leagues would have been a lot for my body to handle all over again at the age of 37, honestly, if I was probably 25 or 28 or probably even 30 again, I would definitely do it and
His family including his two-year-old son also played a part in Jackson’s decision. He says, “At this point I want to spend time with my family. I wanted to see my son grow up. I want to watch him crawl and walk and be there and spend time with him.”
Prior to announcing his retirement, “Smiley J” had already begun activities that most players save for retirement, he published a book and started a podcast.
The book, 9 Innings to Your Best Life, according to Jay, is a “positive mindset book to make sure that you always stay positive. You can always find something in that book, I feel like, that you can use at any time throughout your life. If it’s good, bad, indifferent, I feel like you can find something in that book that can help you just have more of a positive outlook or have just a more successful day or just find a little bit more happiness that you might be missing at the time.”
The Podcast, The Brushback Podcast, is a project he’s had going since early 2024 with former Seattle Mariners outfielder and current Lancaster Barnstormers hitting coach Trayvon Robinson. Both were active players when they began the podcast. They’ll likely be expanding their podcasting projects by the end of the year.
The S.M.I.L.E. Zone is the latest project Jay’s launched. The S.M.I.L.E. Zone is a mentoring and coaching program that will be operated by Jay, Trayvon, and other coaches with extensive experience. “I have that are joining me with the S.M.I.L.E. Zone have all either played at least at AAA and 90 % of them have played in the MLB and overseas too,” elaborates Jackson. “So we’re we’re working with great mindset people to let let your athletes know how to make sure they’re using themselves and their minds the best to get the best out of them and be themselves the best that they can.”
“I was actually a philosophy major in college. So it kind of worked out. And then as I’ve grown through my life, I’ve taken the principles that I’ve learned through the old philosophers and the stoics and everyone, and kind of just seeing the things I’ve gone through and kind of things that have worked for me, but also things that society can take along with it.” Jackson continues. “I honestly think that like what I’m teaching in these principles can just vastly help just everyone be a little bit happier and a little bit more positive, which becomes a snowball for me to compound into other things and lead to other places and help you just live the best life that you can.”
The full article can be found at: https://www.catchupbaseball.com/post/jay-jackson-is-genuinely-trying-to-change-the-world