Windermere Prep senior receives appointment to West Point

Windermere Prep senior Grace Bennett is the first Laker in school history to be appointed to the U.S. Military Academy at West Point.

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  • | 12:59 p.m. February 20, 2019
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For many, federal holidays such as Veterans Day are a welcomed day off work.

For Windermere Preparatory School senior Grace Bennett, it’s a day that completely changed the trajectory of her future career path.

It was a veteran’s message to students during a Veterans Day assembly at school more than three years ago that connected with Bennett. The speaker talked about why he went into the military — to protect and serve the country he loves. It’s what motivated her to look into joining the U.S. Air Force or Navy.

And it’s because of that motivation that the Windermere resident recently became the first student in school history to receive an appointment to U.S. Military Academy at West Point.



Following the assembly that day, Bennett began doing some research on careers with the military. But it wasn’t until her junior year that she got close with her softball coach, JD Wood — a veteran of the U.S. Army in special operations as a ranger with the 3rd Ranger Battalion who also spent time with the 7th Special Forces Group. Wood was the one who helped her prepare for the Candidate Fitness Assessment.

“We would work out every morning at 6 a.m. before school,” Bennett said. “I would work out every other morning with him, and he was training me for Air Force, but he’d been in the Army for so long and he was saying, ‘Hey, you should check out West Point.’ When I went to visit, I loved it. The visit was what made me feel it was my top choice. 

“The campus is beautiful, and everyone there was beyond respectful and very nice,” she said. “Getting to meet the other cadets and teachers and go to classes was really huge for me in realizing I wanted to go there.”

It helps that Bennett holds a 4.2 weighted GPA and has been a multi-sport athlete throughout her high-school career. She has played volleyball and basketball, and continues to shine on the softball field after coming back from a torn ACL and sprained MCL her sophomore year.

“My sophomore year I was playing basketball,” Bennett said. “I was running along the court and stopped too hard and my knee popped the wrong way. … It took about a month for the surgery to happen, and I spent six months doing physical therapy. I came back and played varsity volleyball the next fall and basketball in the winter, and then varsity softball spring of junior year. 

"It’s such a shift, but it’s something I’m excited about. Being in the military is something I’ve really aspired to do for a long time, and I’m excited to reach that goal.” - Grace Bennett

“After missing as much class as I did for the surgery and everything, that was honestly one of the best semesters grade-wise that I had, ironically enough,” she said. “I had actually gotten more athletic when I was recovering, because I was working out my legs every day.”

She applied to West Point her junior year. As part of the application process, she had to receive three congressional or military-service nominations.

“I had interviewed with all three of my Florida nominating sources — Marco Rubio, Bill Nelson and Val Demings — and so I had gone to the interview and thought it was OK, but I wasn’t sure how things were going to go,” she said. “I ended up getting a letter that I got a nomination, and about a week later got an email from my admissions officer saying I got a priority nomination (from Val Demings). I was no longer competing for a spot: I just had to make sure everything was compete and filled out.”



On Saturday, Feb. 2, Bennett opened her application portal to the message for which she had been waiting: She was officially appointed to West Point.

“What really made it real in my head was I got the (acceptance) booklet/certificate in the mail this past Monday, and for me, it was really cool,” she said. “I really am very happy and very, very proud, honestly — not even just the fact that I accomplished it but that I’m actually going there. It’s something I’ve wanted … for a long time. It’s such a huge honor to be selected.”

Despite her success, she credits Wood for his time and dedication toward supporting her in her endeavors and achieving her goals.

“I joke about this, but it’s true: I saw him more than either of my parents last year, because I saw him to work out every morning and after school for softball,” she said with a smile. “He’s a very strong motivator, and he’s also big on the whole thing where if you work for something it’ll happen. You can’t put half effort into something and expect it to work out your way. 

“It was encouraging to have someone get that excited and give me sort of an inside look at the world of what I’m entering,” she said.

For now, Bennett continues to focus on her academics, athletics and other extracurricular activities. She is enrolled in the full International Baccalaureate program at WPS and takes four of these rigorous courses — physics, mathematics, economics and English. She is also president of the robotics club and preparing for softball season to kick off in full swing.

She will leave for West Point July 1 and is looking at majoring in electrical engineering. She said she would love to go airborne and fly helicopters before going back into electrical engineering and contracting work.

“I’d love to stay career military just because I think it’s a great thing to do, but if I were to go out and work in a civilian job, I’d love to work for Lockheed Martin or Boeing,” she said. “I’m just excited for the whole lifestyle change — it’s so different than living in Florida with your parents going to high school. It’s such a shift, but it’s something I’m excited about. Being in the military is something I’ve really aspired to do for a long time, and I’m excited to reach that goal.”


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