"To have a great-great-grandfather who went in 1882 - he got a scholarship from Ponsonby - and to have the fact that we've all continued to go."
Benjamin's family have only recently moved near the school, and he had originally been enrolled as an out-of-zone student. He said the decision to attend Grammar wasn't just about family ties.
"I guess it is a bit of that [family tradition], but I also enjoy sport, and it's just a cool school."
And while Grammar prides itself on its traditions, the Gaze family confirmed that a few things had changed over the years.
Stuart and Franklin, Benjamin's grandfather and great-uncle, both recalled military drills under the hot sun soon after they enrolled, using rifles recently decommissioned from World War II.
Franklin, 80, travelled from Papatoetoe to the school every day by steam train.
"We had the whole carriage full of Grammar boys, another carriage was for King's College, and there used to be some high-jinks that went on between those two carriages, I can tell you."
Another vivid memory was watching the 1st XV, who at the time played their matches at Alexandra Park.
Stuart, 72, said it had not been easy starting after his brother Franklin, who was school dux. "I had this big reputation to live up to ... but I loved being here because of the history, and I loved my sport, and I had a great time."
He, too, had his start at Grammar marked with a photo in the Herald, after a photographer spotted Stuart and his mother picking up the uniform in the John Courts Building on Queen St, now occupied by Whitcoulls.
"It's very exciting for my grandson to be starting," he said, holding the yellowing newspaper clipping. "It seems like a long while ago since I was here in 1955, but those were good days."
Headmaster Tim O'Connor said the school had built several strong relationships with families since it was established in 1869. "Having five generations of one family entrust their young men into our care is very special and highly valued by the school."
For Benjamin's mother, Nicola, this week's milestone wasn't too different from that experienced by the families of 500 other third-formers (still the term at Grammar) filing through the gates. "I just can't believe he's starting high school."