Michael J. Winfield Sr. embodies the ideals of education

By Aidan Johnson

Being a teacher can mean more than just helping kids learn arithmetic and reading. Teachers have the power to leave a lasting impression on the lives of their students. Such is the case with Michael J. Winfield Sr.

Winfield, who has been an educator for over 25 years, with teaching and administrative posts at Shoreham-Wading River, Riverhead and South Country school districts, among others across Long Island, currently serves as a sociology instructor at St. John the Baptist Diocesan High School in West Islip.

Though an accomplished educator and administrator, he did not originally intend to go into that field.

“I kind of backed into it,” Winfield said in an interview. “I was transitioning from my business … and I went back to school, and I was going to stay in security.”

While Winfield was working in the security sector, he wanted to get his master’s in sociology. However, after a deal for the security company to pay for his master’s did not pan out, he left and began working as a substitute teacher.

Although substitute teaching was supposed to be only temporary, he found himself enjoying the work.

Teaching was “something that I just kind of warmed up to,” Winfield said. “Before you know it, I was in my master’s program, and I was taking additional courses to get my teacher’s certificate.”

As an educator, Winfield knew it wasn’t just his job to know what to teach kids; he also needed to understand how to teach them. He described how if his students needed help understanding a particular subject or concept, he wouldn’t automatically fault them. Instead, he would ask himself what he could do better to help register with them.

“I think the students appreciated that because they needed those opportunities, those extra looks at things,” Winfield said. “I always learn from them how I can be a better teacher [and a] better person.”

While students may forget their teachers are still humans, they can still make mistakes. Winfield never felt afraid to admit or apologize to his students if he was having a lousy day.

But Winfield’s efforts continue beyond the classroom. While at Spring Valley High School, his supervisor tasked him with creating a Black History Month program that also included all members of the community.

To achieve this, Winfield focused the celebration on community member Edmund Gordon, a well-known psychologist and mentee of W.E.B Du Bois (an American sociologist, socialist, historian and Pan-American civil rights activist), and created a community service award for him and his wife, Susan Gordan.

Winfield also partnered with community-based organizations to bring his diverse community full of different ethnic backgrounds together during a single event.

“We just had so many different people that all came and participated, and really that’s the goal: to share the history with everyone,” he said.

While these types of celebrations can help expand a community’s knowledge of Black history in America, Winfield still feels that the U.S. slipped in instructing what Black people have contributed to American history. 

“There are some periods of history, as you must be aware, that were not so good,” he said. “But we have to learn from them. We can’t hide them.”

“I think there are some people in the educational world that feel as though these things are divisive, and they’re not divisive,” he added. “They help us learn from it, and they help us grow because history is instructive.”

Winfield’s dedication to his career shows in his continued advocacy work. He still has students reach out to him and give him updates on their lives.

“I had a couple of students this year that sent me cards, and in one card, the student said that she thanked me for creating a safe space to learn,” he said.

Winfield, who has authored “Mentoring Matters: A Practical Approach to Fostering Reflective Practices,” a book that advises teachers in their formative years, among other books, has successfully left his mark on the community around him. For that, he is invaluable.

Michael J. Winfield Sr. is also listed in “Marquis Who’s Who.”