Each morning a loud whistle can be heard as Kirk Gregory in his plaid flannel, jeans, and an old pair of converse walks into the building carrying his lunch box.

After 32 years in the Aspen School District and countless hours dedicated to helping AHS students, Gregory will be leaving his comfortable school year routine to travel, work around his house, and experience new things outside of the only career he has ever known. Student and staff alike will miss Gregory deeply, who is known for his wit, positive attitude, and long history at AHS.

“I am going to miss his sarcasm and his ability to connect with every student. He also creates a humorous atmosphere in his classroom that makes his class fun to go to, and it makes students more willing to learn,” junior Brooke Pisani said.

His long time colleague Andy Popinchalk agrees.

“I think Kirk is one of the best teachers this school has, and has had. He set the standard way before of engaging kids with humor. He’s a very funny guy. There is no doubt about it,” Popinchalk said. “That humor is a way for him wheedling his way into the kids thinking or heart. That endears him to people.”

After many years of experience Gregory has gained knowledge on the profession, and also discovered a new perspective on students.

“What have I learned? I think I’ve learned to appreciate the differences in students, and that you need to value those differences and not expect them to all be the same. I’ve learned to trust kids. Trust them,” Gregory said. “Sometimes when you are younger you’re like ‘you guys are trying to pull a fast one or something,’ and I’ve come to the conclusion that most kids are very honest, hardworking, and they’re going to be truthful.”

The students and the characteristics of the students at AHS are one of the things Gregory will miss the most after retiring.

“I like the classroom. I like the engagement; I like the energy that as a adult you derive from young people,” Gregory said. “They’re optimistic; they’re funny. It is one of the things I’m a little worried about. I’m going to miss that.”

Gregory has taught freshman all 31 years he has been teaching at AHS, and he now also instructs juniors and senior through the IB Diploma class Theory of Knowledge. Throughout 32 years, many things with the district have changed, such as the increase in students from approximately 270 students to 540 today.

“The thing that’s changed a lot that I didn’t anticipate is the growth in the school. It’s bigger. In the last 32 years we are twice as big. It changes the school because it used to be I had every ninth grader. Every ninth grader came through geography. But now I don’t. We have other people teaching and you don’t know every kid as well as you did,” Gregory said. “So, it changes in that you don’t know your colleagues as well, and you don’t know all the students as well as you used to.”

Though Gregory may not know every student, administrator, or teacher at the school, the people he has taught or worked with have been impacted profoundly as a result of having Gregory teaching at the high school.

“Kirk and I forever referred to each other as office spouses. He is my office husband because we are so closely associated with each other and we have worked so closely with each other,” said Karen Green who teaches IB Global History and Civics. “Always having a sense of humor and yet still keeping your passion about teaching, is one of the most important things I’ve learned from Kirk. We have served on committees, worked together for a long time and he’s very funny, and with his levity he really relieves a lot of stress and pressure and tension sometimes when we are in groups together.”

Mr. Popinchalk agrees and recalls a similar experience when working with Kirk.

“When he was president of the AEA, he was remarkable. He was such an advocate and very informed and very capable in leading the teachers,” Popinchalk said. “I thought that he’s willing to say what he thinks, and it always comes from truth and I think a very high ethical standard. He’s a good man. A very good man.”

Gregory’s colleagues appreciate all he does for them, and students appreciate Gregory’s less serious and unique teaching style.

“He has great energy and seemingly endless experience that he passes on to his students through his always humorous stories. He makes every class interesting and entertaining,” senior Griffin Steven said.

His legacy of entertaining classes cannot continue forever. When Gregory started teaching, his goal was 30 years before retirement; now he has made it past his original goal, and as changes in education are occurring, he sees this year as an opportunity to create new experiences.

“I had a student a few years ago who looked at me and said ‘So how long you been doing this?’ And at that time I think it had been 28 years, so I said ’28 years’ and he said, ‘well don’t you ever want to do something different?’ So after I told him to shut the hell up it got me thinking that there are things I want to see,” Gregory laughed.

Gregory plans to spend next year traveling with his wife, fixing up his recently remolded house, and possibly working as an ambassador on Aspen Mountain. While he is excited for the future, he is nervous to change something he has been doing for so long.

“I’ve always been doing this, and I’ve been in a groove that I like, and leaving it is a little scary,” Gregory said.

Gregory will also miss many aspects of the school, such as the Ex Ed program.

“I laugh more on Ex Ed than any other time in my life. I’ll miss that. I’ll miss a lot of laughter, some really good humor. That happens in the classroom too, but when you are on the road somewhere and doing stuff there are situations that are pretty hilarious,” Gregory said.

This year, Gregory claims, was a great year, and while he wishes that he could teach forever the responsibilities and the grading have helped him decided this is a good year to try something different. Student and colleagues of Gregory are grateful for having been able to get to know him, and he will be missed as he leaves the AHS community.

“I’ve always thought of Kirk as something of a model, a role model, and on some levels an adviser because he is very wise,” Popinchalk said. “The way he maintains the up-ness of his colleagues just by his presence and his willingness to diffuse a really serious or depressing reality with humor has done so much for all of us.”