RICHMOND, Va. — Former Flying Squirrels outfielder Jacob Heyward has made a seamless transition from player to coach, landing his first managing position with the San Francisco Giants' High-A affiliate in Eugene, Oregon.
For many Flying Squirrels fans, Heyward's lasting memory came during the 2019 Eastern League All-Star Game at The Diamond. His solo home run helped propel his squad to victory and earned him MVP honors.
"It's just one of the best times of my life, you know, just being able to celebrate that because I had a lot of family coming to town, man, and, and being at home my first year in Richmond, it was just exciting to be there for the fans and, and to really put on for Richmond. It felt great," Heyward said.
Heyward spent three seasons at The Diamond — something of a lifetime in minor league baseball — and had the time of his life career-wise. He cherished connecting with fans throughout his tenure.
"You get to see the season ticket holders who've been out there all season, you know, come out in the first row down the first base line, talk to them, catch up with them, sign as many autographs as possible. Just being there for the fans, it's always important," Heyward said.
When his playing career ended in 2023, Heyward wasted no time transitioning into coaching. And he didn't have to change employers to do it.
"As a player, at some point you always know your career is going to end, and I always knew I wanted to be back in the game at some point. And for me to be able to do it right away, as soon as I finished playing, it was incredible, best experience of my life. They've seen me grow as a human being and for the Giants to be able to give me this opportunity, man, I can't be nothing but grateful," Heyward said.
The opportunity is his first affiliate managing position in Eugene, Oregon, with the Giants' High-A team — the last stop before players come to Richmond. Heyward's gut tells him he's ready, and those who make such decisions agree.
"He's very driven to keep getting better and better just like he was as a player, which is what the fans in Richmond saw all the time, the character, the makeup. But he's, he's determined to be really great at this, and he's, every day trying to get a little better," said Kyle Haines, director of minor league personnel for the Giants.
Heyward understands the importance of his new role in player development.
"High-A is a really, a really important part of your career because you're sending guys to the next level in Double-A, so I take a lot of pride in that. I'm just ready. I'm excited. I'm not nervous at all. I just really want to put the guys in the best position to win," Heyward said.
His connection to Richmond makes his new position even more meaningful for the Flying Squirrels organization.
"Having a direct impact on the guys coming to us is, is, I'm very fortunate to have that because I know what I'm, I know what I'm going to get because of the type of player that he was and the type of coach that he is," Flying Squirrels manager Dennis Pelfrey said.
Heyward plans to take the lessons he learned as a player and impart them from the other side of the conversation, having been where his new players are and where they want to be.
"He's determined. Um, he's a student of the game. He, he's always trying to learn, you know, this side because he switched very quickly from a player to a coach, and that's a tough transition, and I think that he's handled it really well," Pelfrey said.
Heyward embraces the learning aspect of his new role.
"You know, as a coach, you want to say that you know it all, but you don't, and I think you can learn a lot from the players as well, from the coaching perspective. So I think it's really big to just be a mentor, be a leader, be that guy that, you know, when they want to talk to somebody that you'll be there for them. Just understanding there's different ways to coach, different ways to teach, different ways to play the game, and just being humble in that mindset," Heyward said.
Although he played his last game for the Squirrels in 2022, Heyward has a chance to make team history. He is believed to be the first former Flying Squirrels player to be named a manager at a Major League Baseball affiliate when he takes over at Eugene later this year.
That's the same team where current Squirrels manager Dennis Pelfrey used to call the shots, creating another connection between Richmond and Eugene in the Giants' organization.
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