Think it depends on how the school is viewed, i.e. a cherished community institution vs. an obligatory pit-stop on the way to college.
If it’s the former, trophies dating back decades suggests a long history of success to be proud of, and perhaps gives the student pride in knowing he/she is a part of something bigger.
Thinking of my Brother-In-Law, he has trophies at his school dating back to the 80’s. It’s the same school his daughter would attend years later, and walk by her Dad’s trophies each day.
Thanks for posting this - best comment on the thread.