DRAFT DAY DREAM: Windermere High alum gets drafted by San Diego Padres

The San Diego Padres selected Carson Montgomery in the 11th round of the 2023 MLB Draft. He is a former pitcher for Windermere High School.

Carson Montgomery played for the Florida State University baseball team for the 2021, 2022 and 2023 seasons.
Carson Montgomery played for the Florida State University baseball team for the 2021, 2022 and 2023 seasons.
Courtesy photo
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Baseball is a lifelong passion for West Orange native Carson Montgomery.

And most recently, that passion became a career. 

The San Diego Padres drafted the Windermere High School alum in the 11th round of the 2023 MLB draft as the 341st overall selection of the draft. 

“I’ve been dreaming of being a professional (baseball player) ever since I started playing,” Montgomery said. “When I found out it was possible to play the game as a job, I fell in love with the idea.” 

Montgomery, a pitcher, graduated from Windermere in 2020 and then continued playing at Florida State University. Montgomery was the No. 211 prospect on the Top 250 Draft Prospects list. He became the third FSU player to be selected in the 2023 MLB draft, along with teammates Jackson Baumeister and Wyatt Crowell. 

Carson Montgomery signed with the San Diego Padres after his arrival at the Peoria Sports Complex in Phoenix, Arizona.
Courtesy photo

“It means the world to me,” Montgomery said. “It has always been my dream job, and to be able to finally start my career with such a great program (the San Diego Padres) — it’s incredible.” 


Carson Montgomery began playing baseball when he was only 4 years old at Windermere Little League. He stayed there for five years before joining the Warrior and Stingers travel ball teams, which he played for three years. Over the years, he played for the USA baseball team, Power Baseball travel team, West Orange High School and Windermere High School. 

“Carson has been blessed with a gift and always has been a skilled athlete,” his mother, Connie Passilla Montgomery, said. “His hard work, focus and dedication to baseball is inspiring, always striving to compete at the highest level. Being a good leader and teammate have always been important to him. He was named as one of the captains this past season by his Seminole teammates.” 

When he was 17 years old, he was part of the MLB Prospect Development Program, was invited to play at the Perfect Game All-American game at the San Diego Padres stadium, and participated in the Under Armour All-American Game in Chicago and in the East Coast Pro series. 

“I couldn’t be more proud of — or happy for — him,” his father, Corey Montgomery, said. “Carson was always a gifted athlete. He had tremendous unbridled ‘tools,’ as they say in the baseball world. The key for his success thus far, and for his future success, is to continue to work on harnessing those tools and become the polished big leaguer that we all know and believe he can be.” 

For Carson Montgomery, being on the baseball field — even to this day — brings back the early memories of when he used to be at the baseball fields of Windermere Little League with both his brother, Cameron, and sister, Callie. 

Carson Montgomery is training at the Peoria Sports Complex in Arizona.
Courtesy photo

“The first memory I have of being on the diamond is being at one of my older brother’s practices shagging balls in the outfield,” he said. “My favorite memory is being on the field with my brother and dad just practicing. And, (that) I was blessed to represent my country and play for Team USA last summer in Haarlem, Netherlands.” 

Being drafted by the San Diego Padres will now provide Carson Montgomery with the opportunity of a lifetime, where he will be able to learn more of the game from the best coaches and players. 

“I am looking forward to picking the brains of the great baseball players I’ll be around and finding out what made them successful,” he said. 

Shortly after he was drafted, Carson Montgomery was called to the Peoria Sports Complex in Phoenix, Arizona, where he currently is training. 

“The days have been awesome outside of the 115-degree heat,” he said. “I’m starting to get used to it. I’ve had meetings, training (and) workouts. I’ve learned a lot from the staff here in a short period of time. I’m looking forward to the weeks ahead and what I will learn.” 

This was the second time Carson Montgomery received an offer to go pro. The first was back in 2020, but having just graduated high school and amid the COVID-19 pandemic, he decided to turn down the offer to pursue his college career at FSU, where he pursued a degree in business management and finance and became a pitcher for the Seminoles.

“It has been endless hours of studying the game, practicing, working with pitching coaches, working on sport specifics with trainer, working with therapists on massage (and) mobility, nutrition and plenty of rest,” Connie Passilla Montgomery said. “He has matured so much as a pitcher and is ready to continue to learn and compete as a pro.” 

A considerate, kind-hearted, thoughtful, caring and hard-working individual, Carson Montgomery is ready to continue honing his skills on the diamond. 

“I’m investing everything I’ve got into this career in baseball; I only get one shot at it,” he said. “I definitely plan to finish my business degree from FSU online.”



Andrea Mujica

Staff writer Andrea Mujica covers sports, news and features. She holds both a bachelor's degree in journalism and an MBA from the University of Central Florida. When she’s not on the sidelines, you can find Andrea coaching rowers at the Orlando Area Rowing Society in Windermere.

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