By

Portland History

By: Doris Sherrow
Portland's Town Seal
You've seen Portland's town seal, of course, the bearded old fellow in the vest and battered hat, driving a team of oxen? That seal was created by Portland native Philip Gildersleeve in 1966. Gildersleeve was chairman of Portland's 125th anniversary celebration, and drew the seal for the history written by William Van Bynum. The original had his initials in the lower left corner, and "1841-1966 Portland, Conn." above the picture. Both have been removed in its subsequent use by the town.
Phil Gildersleeve was well known as a cartoonist. He drew hundreds of cartoons for the ham radio operator's magazine QST. He was a ham radio operator himself, and had worked as a radio operator on merchant ships. He held various radio licenses since the age of 16 and won several awards for high-speed radio-telegraphic reception. He could transmit 60 words per minute in Morse code! After his untimely death in 1966, QST published an entire book of his cartoons, entitled Gil: a Collection of Classic Cartoons from QST.
Portland Public Library, fittingly, has a copy of the book, but I warn you: these cartoons are virtually incomprehensible to anyone not versed in ham radio! They span the time period 1927 to 1966, and are drawn in a sort of 1930s style reminiscent of Gasoline Alley, Felix the Cat, or the Katzenjammer Kids.
"Gil" (Phil's signature in each cartoon) created the mythical Podunk Hollow Radio Club, with "Where's Waldo"-type pictures sprawling over the page, depicting the idiosyncrasies of a group of radio enthusiasts getting together. The cover for the June 1964 issue of QST, for example, shows the Podunkers, hundreds of them, happily camped out in a forest
setting. In the large tent in the rear, several are operating their radios. In the foreground, several more are chatting up a couple of attractive girls in a convertible, little cartoon hearts fluttering over one ham's head. And off to the far right, the Department of Conservation is beginning to set up their blasting apparatus with its accompanying signs of "Turn off all two-way radios!"
He drew a good many Jeeves cartoons, depicting the faithful butler serving his ham operator master. His first one, from February of 1940, is one I can relate to: from the other room comes the master's voice, saying, "Jeeves, come here and help me look for DX!" Jeeves, as uncertain as I am as to what "DX" is, is coming on the run, carrying a road map, a telescope, binoculars, a lantern, a compass, and a butterfly net! (DX, according to long-time radio operator Gordon Barker, is distance--how far away you can reach.)

Gildersleeve's interests were not limited to ham radio. He began working for the Middletown Press as the Portland correspondent in 1940, became county editor in 1943, then city editor in 1945. Some time later, he was named news editor. His cartoons also decorated the Press, and various trade journals as well. He served in the volunteer fire company, and was captain of Fire Company No. 2 for nine years. He was on the Board of Education for eight years, and served as a vestryman for Trinity Church.
In the words of QST, "Gil became a silent key in 1966…" (think of the Morse code key, stilled from clicking out its messages). He created the town seal mere months before his death.
His seal pulls together a surprising number of elements of historical Portland. Foremost is an old-time oxen driver with his team, pulling a large brownstone sling. The greater part of Portland's 19th century wealth came from the brownstone industry. To the left of the oxen is a small building like those visible in old pictures of the quarries. Its tall chimney is smoking, connoting industry. To the right is another such building atop the quarry wall, with a pulley for lowering things into the quarry.
The majesty of the quarries is suggested in Gildersleeve's use of the quarry wall as part of the background. Many artists would have set their characters on a plain background. Despite the limitations of a two-inch circle, Gildersleeve has limned in the stark, rising blockiness of the quarry wall directly behind the brownstone sling.
Filling in the rest of the background is the elegant sail of a schooner of the sort used for shipping the brownstone in its heyday. Not only was this a significant part of the brownstone business, it harks back to earlier days when Portland was less of a brownstone supplier and more of a shipbuilding center. In fact, it may be no accident that the schooner rises more or less from the center of the seal, since shipbuilding was the source of the 18th century wealth of Portland, a starting point from which other industries flowed. Gildersleeve's own great grandfather, Sylvester Gildersleeve, was Portland's most prominent shipbuilder.
I owe a particular debt of gratitude to Phil Gildersleeve, or maybe to his wife Florence. They lived in my house in the 1940s, and they acquired a copy of the Colonial Dames research on it. When I bought the house in 1972, I had absolutely no interest in history. But I kept looking at these shiny old brown photocopies of deed transcriptions and genealogy, and history began to move into my brain. And that path less traveled has truly made all the difference for me! I only wish I could have met Phil Gildersleeve; his seal is intricate and graceful, but it sounds like his character and personality are the things for which he is best remembered.