Get to Know Trumaine McCaskill, Assistant Principal, Oakland Mills High School

The Get To Know series was created to help staff learn more about HCPSS leaders in schools and offices with whom they may not typically interact. HCPSS leaders answer a mix of personal and professional questions in an effort to let all employees get to know them better. Please use this form to nominate an HCPSS leader to be featured in the series.

Graphic of a classroom. White box on top of graphic with a photo of Trumaine McCaskill. Text reads, Get to Know Trumaine McCaskill, Assistant Principal, Oakland Mills HS. Also in white box is the Oakland Mills High School logo

Why did you choose to work in education?
I chose education because I saw the need for people like me in the field. In a country where less than 2% of public school teachers are Black men, there is no surprise that Black boys are also the group that is least likely to graduate from high school. I felt this firsthand. Throughout elementary, middle, and high school I struggled to find mentors that could relate to my struggle as a young Black male in a majority White setting. Combined with my love and passion for History, education was a no brainer for me. It has become my passion and I love educating and mentoring students from all walks of life.

What is the best professional advice you've ever received?
Keep your promises (or at least make a genuine attempt). Being a leader means you are responsible for answering to hundreds of students, staff, and family members. They rely and depend on you to be a man/woman of your word. Because of that, it is essential to be trustworthy and dependable. If you commit to be somewhere or to do something, you have to put forth the effort to put actions behind your words.

What is something you like a lot that would surprise people?
Thanks to my father, I am still a WWE fan. He and I watch Monday Night RAW every week and call each other to recap. This has been our tradition for years. Years from now, I hope to do the same with my son.

What is on your bucket list?
Learn how to play the piano (or any other instrument). If I've learned anything from the AMAZING Fine Arts department at OMHS, it is that music is a language that most people never get the opportunity to tap into.

What is the most interesting place you’ve ever been?
I was fortunate to travel to Cuba in 2017. If possible, I would recommend anyone to go to experience the culture and history, and learn, firsthand, what the country is all about.