Fleming grew up fishing and playing baseball with his three brothers. He dreamed of making it to the big leagues but also wanted to be a teacher.

His time as a student at Florida Atlantic University gave him the best of both worlds, as he was playing baseball and substitute teaching on the side.

He soon caught the attention of his high school principal, who offered him a job. Fleming, who had earned his degree in history, accepted only to discover there were no openings in history or physical education, which he was also interested in. He decided to take a chance and became a driver’s education instructor.

When Fleming stepped into his office at West Shore for the first time 17 years ago, no one knew the incredible impact he would have on the school.

Although he was walking on an unexpected road, working at Killian High School offered Fleming opportunities that would take his career to unimaginable heights.

After three of his colleagues left the school, he became the head of his department when he was 24. He managed 800 students a semester so successfully that the principal soon offered him an administrative role.

As he moved higher up the leadership ladder, his future in education seemed set.

Then, in August of 1992, Hurricane Andrew struck.

The Fleming family relocated to Satellite Beach in 1994, and Rick Fleming took a job teaching social studies and coaching football at Hoover Junior High School in Indialantic. In less than a year, he was hired as the boys’ dean at Rockledge High School. In 1998, he served as a 12-month assistant principal at Cocoa Beach Junior/Senior High School until 2002. After that, he led Jefferson Middle School as its principal, where he stayed before moving to West Shore in 2006.

Spanish teacher Alexandra Stewart said she has worked for other principals who would distance themselves from their staff members. Fleming, she said, acts differently.

“He is an attentive principal,” she said. “He makes it a point to go around and say hello to all the teachers every week. [If] he’s crossing you in the hallway, he’ll stop and say hi. Even if he’s having a conversation, he’ll stop, say hello and then go back to the conversation.”

(Aaron Murphy)

Media Specialist Mike Drake met Fleming about 26 years ago when Fleming transferred to Cocoa Beach High School as the assistant principal. In 2002, Fleming moved to Jefferson Middle School to be its principal and convinced Drake to follow him. Drake switched schools with Fleming one more time when he became principal of West Shore.

“He always says, ‘I just hire people that care about kids. If they care about kids, all the other stuff will work out,'” Drake said. “As long as you care about kids and you’re doing what you’re supposed to, he’s on board. You can’t ask for much more than that. If Mr. Fleming were at Titusville High School, I’d be at Titusville High School. There was a chance when he was at Jefferson [Middle School] before he came here [that] they were going to ask him to be the principal of Cocoa High School. And I was like, ‘Well, I’ll go to Cocoa High School.’”

Robin Fleming visited Cape Cod, Mass., on Labor Day 1988. She happened to meet Rick Fleming, who was playing in the Cape Cod Baseball League, one of the nation’s premier collegiate summer leagues.

“He was leaving in three weeks, so we spent some time together,” she said.

A while after meeting him, she moved to Rick Fleming’s home city of Miami.

“We went [to Massachusetts three months later] in December to go skiing; that’s when he asked me to marry him,” she said.

In 1990, they were married in Miami.

The couple later welcomed a daughter, Katherine, twin sons, Eric and Tyler, and a third son, Bradley, into their family.

Gallery • 6 Photos

Rick and Robin Fleming take a family photo with children Katherine, Eric, Tyler and Bradley.

Katherine Richardson, his daughter, works as a chiropractor in Palm Bay, Florida. She and her husband have three children, whom the Flemings call their “grandbabies.”

“He’s the main reason I worked so hard in my life,” Richardson said. “He encouraged me to always go for my dreams and was super supportive of everything in my life — when I decided to go to chiropractic school, have children, get married. He has always been my biggest supporter and he’s that way with the students, too. He treats you guys like you’re his kids and it shows in how successful the school is.”

Drake and other staff members tease Fleming for repeatedly using the same expressions.

“I’ve been on the graduation committee for many years, and he’ll say it multiple times: ‘This is a very dignified and reverent ceremony,'” Drake said. “He’ll say, ‘If it’s important to me, it needs to be important to you.” Another one, at meetings, he’ll tell parents ‘I’m going to be brief because I stand between you and the door.’ If you’ve been to enough of his meetings, you’ve heard several things multiple times.”

Earlier in the school year, the guidance department revived the tradition of playing “Flingo” at staff meetings, where teachers bring a Bingo card with phrases Fleming commonly uses. If someone marks off a row of the sayings, they must stand up and say “Flingo.”

“Apparently, [someone got a Flingo] while I wasn’t on campus,” Stewart said. “I had missed one staff meeting in four years. I believe it was [Lynne or Geoffrey] Bramlett. [Fleming] thought it was hilarious.”

Other times, Fleming turns to movie quotes.

“He and I will [quote dialogues] to each other and people around us will look at us like, ‘What are you saying?'” Drake said. “One of Mr. Fleming’s favorite sayings is from Eddie Murphy from ‘Trading Places’ when he tells these other guys that he got in a fight with all these people, and they said, ‘How come you don’t have a mark on you?’ Eddie Murphy looks at them and says, ‘Because I’m a karate man. Karate man bruises on the inside.’ He loves that. He says that all the time.”

According to Assistant Principal Glenn Webb, Fleming uses his sayings for more than enjoyment: he uses them to bring people together.

“For any situation, there’s a movie quote he’ll come up with that fits the bill and everybody relates to,” Webb said. “He has a way of bringing people on board without forcing, without faking, just a real approach. He has a way of pulling people together on a team I haven’t seen in anybody else.”

Once he retires, Fleming plans to spend his time fishing, golfing and being with family. One of his brothers, Jim Fleming, owns a multi-million dollar plant nursery in Newberry, Florida. Fleming, a self-proclaimed “plant dork,” helped his brother set up the business and wants to help him deliver plants again.

Jim Fleming tried convincing his brother to work alongside him when his landscaping business took off, but Rick Fleming said his heart was set on education. His daughter said she has seen this quality in her father since she was young.

“He is one of the most selfless people I know,” Richardson said. “He decided it was more important to help mold young minds of the future than to do something else, potentially making more money, and it was very admirable to me growing up. I always admired [my parents] for working so hard, not for the most money, and loving it as well.”

Throughout his 35 years working in education, Rick Fleming has been known by many titles: a coach, a dean, a principal. But before he earned these roles, he was a teacher in a Miami high school in 1988 who knew he found the field he was meant to be in.

“His love is the students,” Robin Fleming said. “He’ll come home and he’ll talk about the students and what this one does, what that one does. He’s ready, but I think he’s going to miss it more than he thinks he is.”