For much of the past offseason, former Toronto Blue Jays fan favorite Kevin Pillar was flirting with retirement until he found a new home with the Texas Rangers for the 2025 season. But for another former Blue Jays fan favorite, things weren’t as lucky. Last weekend, popular reliever Jay Jackson announced on social media that he was retiring from baseball.
Happy #SMILEYJSATURDAY
— Jay Jackson (@Jaxland58) March 29, 2025
This is one of the hardest things I have ever had to do but I’ve been so blessed. I am hanging up my glove and cleats. I got to live a dream for 17 years of my life that I thought I would never wake up from. From a 9th round draft pick out of Furman that pic.twitter.com/xBoVLFzxOt
Jackson had been a journeyman for much of his professional baseball career until he finally found his footing with the Jays in 2023. Despite seeing somewhat limited action over the course of that season, the 37-year-old right-hander was money for Toronto when he was called upon. In 25 relief appearances, Jackson went a stellar 3-1 with a 2.12 ERA and gave up just seven earned runs with nine walks and 27 strikeouts in 29 2/3 innings.
He ended up playing six MLB seasons with six different organizations.
Blue Jays fan favorite retires from MLB
Mixed in among his tenure with the Jays was his unfortunate involvement in the infamous Aaron Judge controversy during a game between Toronto and the New York Yankees on May 15, 2023.
In the bottom of the eighth inning in a game against the Yankees, Jackson gave up a home run to Aaron Judge, which by itself isn't a big deal; Aaron Judge hits home runs off everyone.
But what was notable was that cameras caught Judge’s shifty eyes during the at-bat, which led to Judge being accused of cheating in taking advantage of Jackson in the process.
In the end, Jackson admitted to tipping his pitches, so the controversy quickly went away.
Blue Jays pitcher admits he was tipping pitches when facing Aaron Judge. Story: https://t.co/rundWqAWmP
— Ken Rosenthal (@Ken_Rosenthal) May 17, 2023
Luckily, that didn't end up tarnishing Jackson’s one and only impressive MLB season with Toronto as he ultimately became a player the fanbase loved. Surprisingly, the right-handed reliever wasn’t re-signed after the 2023 season, much to the dismay of the fanbase.
This past offseason, Jackson was hoping for another opportunity with the Jays, but apparently Toronto wasn’t interested in the potential reunion. It seems there weren't any other offers out there that interested Jackson, so he hung up his clears.
Big things in store and nothing but blessings throughout this journey.
— Jay Jackson (@Jaxland58) March 29, 2025
IN SMILES WE TRUST
~SMILEY J~
😁😁
Nevertheless, Jackson left a must-read, heartwarming message on his social media thanking everyone that played an Important role in his long journey, enabling him to live his dream, and now moving on to the next innings in his life. One thing is for sure, Blue Jays fans everywhere have fond memories of his 2023 season and everything that he was able to do for Toronto.
We at Jays Journal would like to send our well wishes to Jackson and his family, and wish him the best in his future endeavors.