Kevin McCaffrey – Upper School English

Kevin McCaffrey


I spent 15+ years in various parts of the insurance industry after I graduated college.  When the opportunity presented itself, I made a life-altering switch to become a teacher.  For the next 21 years (the last 20 as a History teacher for ETHS), I embraced the profession and craft of teaching.  I thought I had reached a new stage in my life when I decided to retire in 2018.  Funny thing, though: that “new stage” hadn’t reached me.  So, I taught Upper School History at an online school in 2018 -2019.  Then, I thought I had reached that “new stage”: wrong.  When Roycemore came calling, I answered with a hearty “yes”.  So, here I am now, practicing my craft in the other discipline I love: literature.  I am blessed to have an amazing wife, three incredible, wonderful, and successful children, and, four grandsons. Oh yes, and two Golden Retrievers who are as naughty as they are beautiful!


  • M.A. (History) Northeastern Illinois University
  • M.Ed. Loyola University Chicago
  • M.B.A. DePaul University
  • B.A. Loyola University Chicago

Fun Fact

In my final year at ETHS, I wore a different Hawai’ian shirt every school day.  And, I had plenty to spare.  Now I’m working on that mask collection.

Why do you teach? What is the impact you hope to make on students?

I teach partly as a tribute to the many great teachers who taught me; partly as a tribute to my father (who recently passed); and, partly as a way to pay it forward and help those who follow me to grapple with the critical questions of: “Who are we?”, and, “How did we get here?”

Why Roycemore?

Roycemore is a community that cares for, and about, each other.  That was so obvious the day I first walked in the door, and it’s still that way now.