The Second Half: The End Leading to a New Beginning
By Derrick Smith ·
The Second Half: The End Leading to a New Beginning
by Derrick Smith, Cronkite News
November 4, 2026
(Audio by Derrick Smith/Cronkite News)Jay Jackson spent 17 years playing professional baseball, but eventually his career came to an end. This episode discusses what led to the end of his athletic career and his thoughts on what his last season in Major League Baseball was like.
In particular, this episode goes in-depth on how Jay felt during his last outing against the Tampa Bay Rays in 2024, and the pitch sequence to his last batter in MLB— Tampa Bay Rays All-Star, Yandy Díaz.
Key takeaways of the episode:
• Injuries to Jay’s knee and shoulder played a part in the ending of his baseball career.
• Jay’s baseball journey was anything, but a straight path. Over his 17 years in professional baseball, he would make it to the big leagues with six different organizations, spending part of his baseball career overseas.
• Even though the ending to his athletic career didn’t end exactly like he had hoped, Jay is proud to have pitched professionally for 17 seasons.
TRANSCRIPT
Derrick Smith: Professional athletes are often viewed as these incredible people who are not like everyone else. They may be able to throw a baseball hard, jump high or run fast. But what happens when the sport they dedicated their entire lives to begins to slip away, ultimately ending before they’re ready to walk away?
And this is exactly what The Second Half is about: life after sports. I’m Derrick Smith, host of the three-part audio series that follows the story of former MLB relief pitcher Jay Jackson, whose professional baseball career spanned 17 years.
Derrick Smith: Jay Jackson’s journey through professional baseball was anything but a straight path. Over those years, he would make it to the big leagues with six different organizations, spending part of his career overseas in Japan, where he helped the Hiroshima Toyo Carp win three consecutive Central League titles.
Jay Jackson: “When we clinched, we all walked out after the game and we went to go bow to our fans. So right when we went out on the field, I literally went out onto the field and I finally looked up to the stands, and I saw how many fans were there. And it was like the coolest thing I’ve ever seen.”
Derrick Smith: Recently, Jay opened up to me about what the end of his career was like and the challenges he faced as he entered his last year in the big leagues.
Jay Jackson: “My last season was a struggle. It was a grind. Honestly, for me, I had had a good year before, in 2023 with the Blue Jays. And after that year and how I had pitched and everything that was going on, I was looking forward to hopefully getting a guaranteed big league deal, and that didn’t materialize as soon as I thought. So honestly, I was in the mode of almost retiring then, and then the Twins came out of nowhere.”
Derrick Smith: The Minnesota Twins signed Jay to a one-year, $1.5 million contract for the 2024 season. However, injuries impacted Jay’s ability to perform at his highest level.
Jay Jackson: “I remember going through workouts feeling pretty good. Then I remember doing some hurdle jumps and I felt my knee tweak a little bit. Didn’t think too much of it. It was fine and I was able to play through it. And then went and had another PFP, something, and my knee kind of buckled again, and I was like, ‘All right, that’s cool.’”
Derrick Smith: PFPs, or pitchers’ fielding practice, are drills designed to help pitchers improve their defensive skills, such as fielding ground balls and covering bases.
Jay Jackson: “But then literally, I was supposed to pitch one day after just an off day during spring training. And I remember during that off day, I went and I did a doctor check and I felt like everything was okay. Then I literally drove back to the apartment I was staying in with my family during spring training and my knee swelled up, and I could barely walk.”
Derrick Smith: Despite this setback, after icing his knee, Jay pitched in a game less than 48 hours later, trying to hold on to the opportunity the Minnesota Twins had given him.
Jay Jackson: “Just pitching through that the whole year, they kept sending me up and down.”
Derrick Smith: In other words, Jay was constantly being sent back and forth between the Minnesota Twins and their minor league affiliate, the St. Paul Saints, throughout the season.
Jay Jackson: “When I got sent down the first couple of times, I was pitching pretty well and I was getting used a ton. And for me to be the oldest guy on the team and having kind of the knee stuff that I was having, I kind of figured that I was going to, you know, be in some places that was going to benefit my role more and help the team more, where I could stay healthy and make it through the season and help them get to the playoffs and try to make this happen. And obviously that didn’t happen. I played through the year, the injuries I had. My knee ended up messing with my shoulder.”
Derrick Smith: The stats back this up. According to Baseball Reference, in 2023, Jay pitched in 25 games for the Toronto Blue Jays, recording a 2.12 ERA and 27 strikeouts in just under 30 innings pitched. However, in 2024 with the Twins, Jay was not nearly as effective. After appearing in 20 games that season, Jay’s ERA ballooned to 7.52 in just over 26 innings pitched.
His last outing against the Tampa Bay Rays was a reminder of how things had turned south. Jay entered the game with one out in the eighth inning, striking out both batters he faced. But when he returned for the ninth, things didn’t go as well. After giving up a home run to Jose Siri and then a walk, Jay found himself facing Yandy Díaz.
Jay Jackson: “I go out for my second inning. I was facing Yandy, and I was like, ‘Okay, I like this matchup. It’s not a bad matchup.’ And I missed with a slider. He pulled it foul or something like that. Then they called two-seamer in. And I was like, ‘Why are we throwing in to Yandy?’ But I was like, ‘Maybe you guys know something better than I do. Whatever. Maybe we’re just trying to show him, not for a strike, whatever.’ But he’s like, ‘We’re going two-seamer in to Yandy,’ and I was like, ‘All right, two-seamer in to Yandy.’ Homer. I looked at it and I was like, ‘Oh,’ because now instead of us being down, I think, one run, we ended up being down by four now. So they pull me out of the game. So that was my last day in the office and my last day of pitching ever.”
Derrick Smith: Jay’s decision to pitch through the pain isn’t unique in professional baseball.
A 2025 study by University of Michigan researcher Richard Paulsen looked at more than 1,100 MLB players.
It found that players with only one year remaining on their contracts missed nearly five fewer games due to injury compared with players with multiple years remaining on their deals.
The research suggests that players whose future in the league isn’t guaranteed may be more willing to play through injuries when their next contract is at stake.
Teams also manage injuries differently when a player isn’t under contract long term, according to the study findings.
For Jay, this meant continuing to push forward, even as his body was telling him to slow down.
Jay Jackson: “Going through injuries for me was literally, I’m grateful that I got to play baseball. And as long as a team kept me on the team and wanted to help me get better, my goal was, ‘How can I get better?’ As long as I had a chance to be out there and got a chance to rehab, even though it sucked some mornings, every day that I got to be playing baseball I was grateful for and I wanted to enjoy.”
Derrick Smith: But even though his last outing in the big leagues didn’t go like he had hoped, Jay is proud to have pitched professionally for so many years.
Jay Jackson: “The average baseball career is probably two to three years. I know I got drafted with a lot of guys that I didn’t see the next spring training. So for me to be able to make it through 17 springs, 17 summers, 17 falls in professional baseball is more than a blessing. I wouldn’t regret it or change it for anything. The good, the bad, the up, the down, it helped me be who I am.”
Derrick Smith: In the next episode of The Second Half, I’ll speak with Jay about how he adjusted to life immediately after his athletic career ended. It’s an episode you won’t want to miss. This is Derrick Smith signing out for Cronkite Sports. Have a great day.
This transcript was generated with the assistance of AI and may contain errors, omissions or misspellings. The audio is the authoritative version. If you notice an error please contact [email protected].
This article first appeared on Cronkite News and is republished here under a Creative Commons Attribution-NoDerivatives 4.0 International License.
Originally published by Cronkite News Sports
