Alma Matters: Baseball shapes DP alumnus' life

Editor’s note: Alma Matters is an ongoing series featuring alumni from West Orange and Southwest Orange high schools who have chosen to stay and become integral leaders and contributors to the community.

Scattered across a dark blue wall in the Dr. Phillips High School baseball locker room are signatures from past alumni. It includes names such as former MLB all-stars and World Series champions Johnny Damon and A.J. Pierzynski, along with some players from Dr. Phillips’ 1996 state championship team. Also on the wall, in silver Sharpie, is Bobby Olszewski’s signature. 

Although Olszewski didn’t make a name for himself playing professional baseball after graduating from Dr. Phillips in 1995, he said the resiliency he learned at a young age competing on the baseball team shaped his time as a Winter Garden city commissioner, Florida state representative and now author. 

“I always joke, I never got to play baseball, so I settled for politics,” Olszewski said. 

Being the backup catcher for Pierzynski, Olszewski said he learned early on the importance of controlling what you can control and knowing your role. And the heightened expectations from parents and teachers is what he said prepared him for careers as a public servant, politically and professionally. 

“At the time, Dr. Phillips was one of the elite baseball programs in the country,” Olszewski said. “So there was a lot of pressure and a lot of focus and a lot of external forces from parents and peer pressure to perform at a high level.”

He said the spotlight always was on the players in those four years he attended Dr. Phillips since the program produced first-round picks such as Damon and Brian Barber, raising the bar for what each player was asked of them.

Meeting expectations and dealing with that sort of pressure was something Olszewski came to handle a lot in his political career, but his path to public service wasn’t a straight line following his time as a Panther. It came after a venture in a different industry before realizing what was right for him. 

A shift to service

After graduating from Dr. Phillips, Olszewski enrolled at the University of South Florida and tried to join the school’s baseball team as a walk-on. He was cut before the season started, leading him to focus more on another passion he had in high school: sports broadcasting. 

The day after being cut, Olszewski walked into the USF Athletics department and earned a gig sideline reporting. It’s something he did as a student at Dr. Phillips, anchoring and reporting for its student-run news production W-DOC, which aired every morning. A highlight from that time in high school was interviewing Shaquille O’Neal at the Orlando Arena following a public service event. 

At USF, Olszewski was featured on Tampa Bay sports radio and did halftime interviews for the USF Bulls Sports Network his freshman year. He soon found a job with Florida Citrus Sports’ PR department, lending him an opportunity to move back to his home town of Orlando and transfer to the University of Central Florida. 

Olszewski graduated in 1999 from UCF with bachelor’s degrees in radio/television and organizational communication. He quickly found himself wanting to take part in his community. 

His parents influenced his drive to help his neighbors. Growing up, he said his mom and dad actively volunteered to help in Little League, church and the Dr. Phillips community. Olszewski’s mother, Rosie, was a teacher at Dr. Phillips for 39 years — including when Olszewski went there as a child. 

“You couldn’t get away with anything, but I didn’t get in any trouble,” Olszewski said about the dynamic with a laugh. “It was fun having people know and respect your mom, and then having her there was great, you always had a ride to school or a ride home, so it worked out.”

After moving to Winter Garden following college, he said he attended every City Commission meeting for two years and figured if he was so involved, he might as well run for a seat on the commission. He always loved politics but another motivation was that an early career in sports reporting didn’t seem as impactful as civil service.

“I saw a lot of my friends working as a sports reporter in, you know, Hopkinsville, Kentucky, making $15,000 a year,” Olszewski said. “I said, ‘I don’t think you can live on that.’ That kind of made me realize there’s other things than being a reporter and being on TV.”

Olszewski won the Winter Garden City Commission District 3 seat in March 2012, earning 70% of the vote to defeat two other candidates, including the incumbent. It was an achievement he had not thought was possible for somebody with his background. 

“I say all the time, I’m shocked I was ever elected to office,” he said. “So many times, you have to come from money or you have to come from a political family.”

Olszewski later was reelected to the commission in 2015 before resigning in 2016 to run for the Orange County District 1 Commissioner position against Betsy VanderLey. Although he lost the Orange County election, just a year later, he won a special election to become the District 44 Florida state representative.

“As always, if you want to make God laugh, tell him your future plans,” Olszewski said. “It worked out better for me to be up in Tallahassee with the relationships and the opportunities that I had to serve my community.”

Now out of office, having lost his seat in the Florida State Legislature to Geraldine Thompson in 2018, Olszewski said he doesn’t miss campaigning, but he does miss helping the residents and voters for whom he worked. 

“I absolutely miss the public service,” Olszewski said. “In politics, when a stranger or constituent calls you, they’re in trouble or they need something or they don’t know where to turn. To be able to help someone like that is very rewarding.”

Away from serving in politics, Olszewski has delved into the world of publishing while trying to keep up with his everyday job.

For the love of the game

Olszewski’s motivations behind writing his first book, “Grand Slam Leadership: Using Baseball Principles and Strategies to Win in Business and Life,” was to use baseball as an analogy to “make things make sense” in a world he believes was gravely disrupted ever since the COVID-19 pandemic. Published Jan. 1, the 55-chapter book blends lessons he learned from playing baseball and applies them to the world of business. 

One example is “Don’t Swing at Every Pitch,” an excerpt that goes over the plate discipline that made the greats like Ted Williams and Tony Gwynn legends in the sport but also how the same principles can apply to being patient when leading in a workplace. 

“As an academic, I don’t think there’s anyone who’s got their Ph.D that says they’ve never thought about becoming an author,” Olszewski said. “So I guess that’s always been in the back of my head. With all the excitement of baseball and the Orlando Dreamers, it just reignited something in me and a year ago this time I said, ‘I’m going to do it.’”

He completed the book by finding time between working as vice president of government and community relations for Global-5 Communications, writing it bit by bit while handling the marketing for the I-4 Express. 

He recently finished another book, titled “Donor Motivations,” based on his doctoral thesis from Northcentral University going over what motivates people to donate to a nonprofit. 

Olszewski plans to write his third book with his daughter, Reagan, with the premise based on Grand Slam Leadership for kids. For now, at least, he hasn’t thought about getting back on the campaign trail.

“You never say never to public office,” Olszewski said. “But, I don’t see me jumping into a campaign anytime soon.”

Olszewski uses his time around baseball as a strong foundation for his life. He looks back fondly on the time he spent playing Little League with his dad as the coach and his mom helping run concession. His dad died unexpectedly in 2003 and led him to cherish his mother more now, calling her twice per day on the drive to and from work. 

When recalling his time at Dr. Phillips High in totality, the fondest memory was ironically not on a baseball field but during a varsity spring football game his freshman year. Olszewski wasn’t supposed to play, but a starter on Dr. Phillips messed up on special teams. Thanks to the error, the head coach grabbed Olszewski and subbed him in the game. What sticks out most was the image of his parents cheering him on from the stands. 

“I just remember looking in the stands and seeing both my mom and dad, just shocked, so happy to see me run out on the field,” he said.