During the past quarter of a century, Massey has produced a substantial body of historical paintings. He is fascinated by certain eras and subjects, and his works tend to group themselves into series which explore a specific place or period or sequence of events: Buffalo harbor (his home town), the Great Lakes steamers, the great explorers - Sir Francis Drake, LaSalle, Magellan, Cook, Vancouver, and the American China trade.

Massey will not commit art to canvas until he knows every conceivable bit of information about his subject. In painting a ship's voyage, Massey signs on, in a sense, as Captain, navigator, and hand before the mast, and by the time his scholarly and artistic adventure is done, he understands the seafarers' experience from stem to stern and every point of the compass.

Although digging into the nooks and crannies of maritime history is Massey's passion, he has for many years been fascinated by the natural beauty of the great Humpback whales and their seemingly timeless migratory passage from the northern Pacific to the waters around the Hawaiian Islands.