Staff Highlight: Mr. Leonardo, A Glimpse Into The Life Of A Talented Teacher And Musician


Zoe Long, Editor/Writer

Winthrop High School is full of so many amazing staff members and students! Although all of them deserve appreciation and spotlight, The Viking Times decided to focus on one particular teacher this week: Mr. Leonardo!  You may know him from teaching you history or intro to psych, the halls of our high school, or our beloved faculty band Staff Infection. Personally, I only met him this year as my APUSH teacher, but he has already left a mark. Mr. Leonardo is a very charismatic, passionate, and engaging teacher and person who creates a fun learning environment, as well as safe space for advice and support. I don’t want to spoil too much about him, as all of that will be answered in the questions we lined up for him, BUT in short he is an incredibly cool and funny person, talented musician, and effective teacher. Without further ado, here’s all you need to know about Mr. Leonardo: 


I started by asking questions about Mr. Leonardo’s life as a teacher. 

Zoe: Do you enjoy being a teacher? 

Mr. Leonardo: I do enjoy being a teacher. Although there are pros and cons to the career, that type of “taking the good with the bad” is a part of life and happens anywhere. Put it this way, it has been the most rewarding job I have had so far!

Z: When did you become a teacher?

Mr. L: After college, I assumed I would end up working for the federal government or in the defense industry and that is where I initially landed when I got hired at Raytheon Company. Although I enjoyed the idea of working there, the day-to-day life and office environment was not my cup of tea, not to mention I missed the academic environment I had in college. So fast forward a couple of years and I began looking at getting into education.

Z: Have you always wanted to become a teacher?

Mr. L: Why would you ask this question, I just told you. Were you not listening? In all seriousness, it had crossed my mind while I was in college. The college professor’s life seemed sweet especially since there was so much time off teaching in the summer. I imagined that job would have given me plenty of time to pursue other passions. Although, now I know that most college professors are eternally swamped in teaching, research, and many other endeavors. Of course, this is not much different from the life of a K-12 educator!

Z: Do you want to continue to be a teacher? 

Mr. L: Yes, I do but I never say never to other opportunities!

Z: What led you to work at Winthrop High School?

Mr.L: No other school would hire me. Next question. Just kidding! In all seriousness, the thing about history teachers is that there are many prospective candidates looking for a job and not enough jobs to go around so it is very competitive. The better question would be to ask Mr. Crombie why he chose me?! Having said that, I am very happy to be a part of the WHS community. I have had a lot of fun working with students, Mr. Donnelly & his digital video students, Staff Infection, and all of the other fun stuff we do around here!

Z: What aspect of Winthrop High do you enjoy the most? 

Mr. L: Although I feel like our morale has been suppressed over the last year or two, I really enjoy the relationships I have with many of my coworkers who have become friends as well as the relationships I have built with students. It is nice watching all of the students move on while getting to see them grow into functional adults…allegedly.

Z: How is your first year teaching APUSH (AP US History)? 

Mr. L: It has been a learning experience but I thoroughly enjoy it. I am hopeful that next year’s group will be as fun as your class! I have some good ideas to mix things up for next semester so there is that!

Z: What is your favorite subject to teach? 

Mr. L: It is hard to have a favorite. I enjoy various parts of all my classes. I could rattle off favorite parts of every class I teach!


Next I asked Mr. Leonardo questions about his music career!

Zoe: What is your favorite type of music?

Mr. Leonardo: I am partial to many genres and styles but if I am really in my element, it is either 60’s Soul/R&B/Pop (e.g., Temptations, Aretha Franklin, Stevie Wonder, Beatles, etc…), Rock/pop from the 1970s and early 1980s (Chicago, Earth Wind & Fire, Journey, etc…), OR late 60’s jazz from artists like Miles Davis, John Coltrane, Herbie Hancock, and many others!

Z: What music do you primarily play?

Mr. L: Gigs have been few and far between due to the pandemic but when I do perform, it is usually in a Chicago tribute, dance band, or jazz group.

Z: When and how did you begin playing music? 

Mr. L: My grandfather was a jazz drummer out of Rhode Island so my father grew up in a very musical household and that got passed down to my childhood. My parents got divorced when I was very young so I spent many hours on the road with my dad just listening to music (much of it from the genres above) and I took to it, particularly the sound of the electric guitar. When I was probably about 5 or 6, I remember hearing the guitar solo on the song “25 Or 6 To 4” by Chicago. At the end of the solo, Terry Kath, the guitarist is using a “wah” pedal which people say makes the sound of a crying baby (strange, I know!). To make a long story lousy, that sound basically changed my world. I was like “what the heck is that?!!!” So since then, music has taken up a lot of my time and thought. 

Z: Do you find it hard to balance both parts of your life? Music and teaching?

Mr. L: Yes. Life and your job will inevitably get in the way of your passion. Few people in the world have the ability to put themselves out there and survive financially just on their passion alone. Props to them since many of them are close friends. It is a decision I made a while ago and although I second guess it once-in-awhile, I never would have been able to have a “normal” family life being a touring musician if I were even lucky enough to get that kind of gig. My grandfather once told my dad when he was a teenager that in order to get to an exceptional level in the music industry, your instrument has to be the only thing you ever think about, no dating, no trips with your friends, etc…the idea being that you have to commit to the craft as few people do in their lives and the music and process and getting better has to consume your whole life. That proposition felt a bit too far when I had to decide if that is what I wanted.

Z: What has been your coolest gig?

Mr. L: Probably back in 2013 when I performed for a charity fundraiser in a band with former members of the band Chicago, current members of John Fogarty’s Band, and many other exceptional performers. There is a funny memory we all have from that day when J. Geils (the former guitarist of the self-named band) opened for the act I was in…so yes, J Geils opened for Mr. Leonardo! But the best part of that night was performing with my dad’s drumming idol, Danny Seraphine, a member of the Rock & Roll Hall of Fame!

Z: Do you have future goals for your music? 

Mr. L: Yes, but will they be fulfilled, see my response to number 4 LOL. I am putting a new band together as we speak and always writing jazz/rock fusion material for an album I may never complete!

Z: Are you planning on releasing anything on Spotify/Apple Music?

Mr. L: Yes, I will most likely finish an album in the next few years and it will be on streaming platforms when that happens. My dream would be to have a few vinyl albums pressed for my own benefit. It would be cool to hold a vinyl version of my own material!


Lastly I asked Mr. Leonardo a few questions about his personal life!

Zoe: What is your life like outside of music and teaching?

Mr: Leonardo: Taking care of a 6-month-old baby is very time consuming (again see my response to number 4 above LOL) but I am always reading on various topics of interest like international relations, Chinese politics/history, democratic backsliding, among other historical or political topics

Z: Do you have any hobbies that you’d like to highlight?

Mr. L: Music is my only “serious hobby” but I enjoy cooking and trying new recipes!

Z: What is your favorite place you’ve traveled to?

Mr. L: Los Angeles took me by storm when I went there back in 2009. It was probably because I romanticized the idea of living there as a guitarist but I also really enjoyed Italy when I went there. I am returning this summer (hopefully…)!

Z: What is your best memory from last year? 

Mr. L: If “best” means good then it was definitely the birth of Mazie in July! It was a roller coaster of emotions or as Ron Burgundy said, “I’m in a glass case of emotion!”

Z: What things are you looking forward to in the New Year?

Mr. L: Hopefully finding balance in my life!


Those are all of the questions we gave to Mr. Leonardo but we hope you enjoyed learning a bit more about him just as much as we did. If you see him in the hallways, make sure to wave or strike up a conversation about Jeffersonian Democracy or Earth, Wind, and Fire! As I mentioned before, he is an incredibly nice person, so I would recommend his APUSH course to most rising juniors or seniors! Thank you again Mr. Leonardo! You rock!