It’s the home opener, and that familiar excitement has grasped Desmond Jennings.
With his team trailing 7-3 with two out and nobody on in the bottom of the ninth, a rally starts: a single, followed by a pair of walks to load the bases. Then a mistake gets sent deep into the night to tie the game. That’s followed by a double, and finally a RBI single to cap off a 8-7 victory.
But Jennings isn’t at the plate this time, instead it’s his first walkoff win as a professional coach.
The former Rays outfielder is working as the assistant hitting coach for the Clearwater Threshers, the Philadelphia Phillies affiliate in the class-A Florida State League. Jennings was in the dugout as Aroon Escobar launched the slam off Daytona Tortugas reliever Nelfri Payano and Joel Dragoo singled home Brady Day off Victor Diaz a few moments later at Baycare Ballpark. But he says the feeling was familiar.
AROON ESCOBAR’S FIRST PRO HOME RUN IS A BOTTOM OF THE 9TH GRAND SLAM TO TIE pic.twitter.com/X2qgkhRDgC
— Clearwater Threshers (@Threshers) April 9, 2025
“Oh man, I got chill bumps. It was unbelievable,” Jennings told me afterward. “Four games into this [season] and this is what we get. You can’t be more excited, especially for those kids. They work so hard.”
“Hard work.” It’s an aspect of the game Jennings is familiar with and something he’s looked to pass on to the next generation after he stopped playing himself in 2018.
“I started coaching travel ball,” Jennings said. “Opened up a facility back home [in Birmingham] where I started coaching and training kids. And then a lot of people were asking me to start a team and I was like, ‘Let’s start a team!'”
Jennings said he worked at the youth level for three or four years before deciding to make the leap into the professional ranks. He attended the Front Office and Field Staff Diversity Pipeline Program put on by Major League Baseball and run by Tyrone Brooks, then reached out to a former coach, retired Rays minor league coach Skeeter Barnes, for the next step.
“That’s my guy,” Jennings beamed. “He was always a mentor and always treated me well. [He] gave me great advice and helped develop me into a decent outfielder and base runner and baseball player in general.”
Soon after, the Phillies came calling with an oppotunity that would allow him to work in a location he was already familiar with, and now he gets to take the messages he learned from Barnes and all the other coaches he worked with as a player, and deliver them to the next generation.
“I’m happy for Desmond,” Rays manager Kevin Cash, who managed Jennings for his final two seasons in Tampa Bay, told me. “He’s going to help a lot of guys, certainly in the outfield. But just the mindset of a major league player and understanding how difficult it can be at times, I would bet on Desmond being able to express that and be a really good coach.”
But is the end-goal to get to a big league managing role like Cash?
“I would never say no, but right now my goal is to have the guys I have right now get better and potentially become Major League Baseball players,” Jennings said. “I love baseball, I love helping people become better at baseball, and I just love being around this game.”
Steve Carney is the founder and publisher of St. Pete Nine. One of the people most associated with baseball coverage in Tampa Bay, he spent 13 seasons covering the Rays for flagship radio station WDAE, first as producer of Rays Radio broadcasts, then as beat reporter beginning in 2011. He likes new analytics and aged bourbon, and is the owner of one of the ugliest knuckleballs ever witnessed by baseball scouts.
