In the early to mid-1920s, the student body was divided into a Senior Class, an “Upper Middle Class,” a “Lower Middle Class,” and “Juniors,” the latter of which appeared to comprise the newest students to the academy. Each of these classes composed a “history” for the annual Milestone yearbook—in essence a bragging rights installment that extolled the merits of each class—some to funny and charming effect. A healthy dose of sarcasm saturates some of the entries. In the 1924 Milestone, for instance, the Juniors’ entry claims:
“After one hundred and sixty years of trial Dummer has at last obtained the perfect class, according to each Freshman. The class entered school this fall and for the first few weeks was completely lost in the whirlpools of inexperience. Now we have recovered from the K.O.’s of the midyears and are approaching our Sophomore year when we hope to look down on all brats with sneering contempt.”
An entry in the 1924 Milestone from the Upper Middle Class notes that the yearbook’s senior editors “drafted into their service one member of our  class, Roberto Andreani, who is busy helping furnish the Year Book with cartoons. Roberto Alvin Ormsby Andreani (photograph below) of Florence, Italy, was a 1925 graduate of Dummer Academy. He was at one time the Art Editor for The Milestone. Under his photograph in the yearbook, it says that “Andy came to us quite a mystery…Eventually we discovered that Andy could draw, and from that moment on he has not had a minute’s peace. Andy is an aeroplane fiend. His sole ambition is to build the wonder plane of the age, and it was no small shock to him to find from an authentic source that most of the aeroplanes he had so painstakingly drawn would be unlikely to fly. Most of us think that if Andy becomes an engineer, a good artist will be lost to the world.”
Andreani’s illustrations were often quite realistic, as you can see from the sketchings of 1923-1924 team captains Travis Ingham (Track), Everit "Terry" Terhune (Football), and John "Doc" Hinds (Baseball), and a photograph of the subjects, below.
The illustrations are a vibrant addition to the Milestones. For your enjoyment, additional Andreani sketches can be seen below.