Spotlight On: James “Pirate” Sullivan

December’s Spotlight is highlighting a popular Holyoke High history teacher, James Sullivan.


If you are a student at Holyoke High School, you are almost guaranteed to know the teacher in “the hidden classroom” of 305, Mr. James Sullivan, also known as “Pirate.”

Mr. Sullivan has been teaching at Holyoke High School for nearly 20 years and has been teaching in the Holyoke school system for nearly 30 years. Throughout his years, Sullivan has taught nearly every branch of history. He has taught Government, Geography, Economics, World History, Law, and United States History. Currently, Sullivan teaches US History II, AP US History, and Law.

Sullivan attended Holyoke Catholic High School, where his mother worked. He then went on to attend Fordham University in NYC and Westfield State. Before beginning his teaching career, Sullivan served his country in the United States Navy. Sullivan originally studied to be a lawyer, but is glad that it didn’t work out and that he is now a teacher.

“I’ve never had any doubt that this was the job for me,” said Sullivan. “I wouldn’t want to be doing anything else.”

Sullivan helps his students develop good writing skills to prepare them for college.  He frequently assigns essays, has his students analyze Historic documents, and gives reading quizzes.  He takes a genuine interest in each and every one of his students and wants to see everyone succeed.

Sullivan still really enjoys teaching even after 30 years.

“My favorite part about teaching is the students. No doubt about it,” said Sullivan, “I really like watching them develop and seeing them acquire skills in reasoning and writing.”

Sullivan still feels that it is a privilege to be teaching even after all this time.

Sullivan has taught hundreds of Holyoke High students, even including some of the current and past teachers of Holyoke High School. Sullivan had Mr. Courchesne, a HHS English teacher and adviser of The Herald, and Ms. Sweeney, a former English teacher at Holyoke High School.

“Mr. Sullivan taught me just as much about writing as any English teacher I had at Holyoke High School,” said Sweeney. “When I started teaching at Holyoke High, he was one of the first teachers I had who welcomed me as a colleague too!”

Ms.Lubold, a current Health and Physical Ed teacher at Holyoke High and graduate of HHS, told The Herald, “I heard from other students in my class when I was in high school, that Mr. Sullivan was a really good teacher. I really regret not taking his class.”

Many current students agree with Ms. Lubold’s former classmates and really like Sullivan.

“Mr.Sullivan is a great teacher!” said Sadie Pecia ’19 and student in Sullivan’s AP US History class. “He teaches us at a high level and helps us develop good writing skills!”

Miranda McKenna, HHS ’18 and student in Sullivan’s AP US History class, also agrees that Sullivan is a great teacher.

“He makes learning fun! He tends to give us a lot of reading quizzes, which we all dread, but thinking about it, I know that they will better prepare us for the AP exam and for college,” said McKenna.

When not in the class room, Sullivan likes to read and play golf. He enjoys having his summers off so he can relax and spend lots of time improving his golf game.

Rumors have been heard that Sullivan may be retiring after this school year. Sullivan said that with a milestone birthday coming up this year, he will soon decide what his plans will be for the future. In the meantime, he hopes to have many more fun teaching experiences and make many lasting memories.