Lee Kennedy: Sleepy Hollow’s Man of Many Flags

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1777 13 star flag designed by Francis Hopkinson under the first flag act

July 3, 2019

by Barrett Seaman –

Drive by Lee Kennedy’s house on Harwood Avenue in the Philipse Manor section of Sleepy Hollow on or around a national holiday, and you’re sure to see the Stars and Stripes flying from the pole in the front yard. If you look carefully, however, you’ll note that it is hardly ever a standard contemporary 50-star American flag.

On Flag Day, June 14, for example, it was a replica of the “star spangled banner” that flew over Ft. McHenry that memorable night in 1814 and inspired Francis Scott Key. This Fourth of July, Kennedy will be flying one of his 13-star flags from the revolutionary period. They will be replicas of what is left of a collection of 300 Continental and American flags, along with British and Scottish forebears of the iconic Stars and Stripes he once owned. He still has some 60 mostly nylon replicas (they fold better and fly more freely) but donated the original collection in 2000 to the Oklahoma Science Museum. The replicas that remain he keeps in a closet where they are stored snugly but neatly—each wrapped in a plastic dry-cleaning bag.

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There was a time a couple of decades ago when Lee and his late wife Sue lived in Millbrook in a 7,000 square-foot house that allowed him to give full display to his collection. There, one could have seen a 35-star flag, which included West Virginia (admitted in 1863) but not Nevada, which joined the union in 1864. He has one unusual flag that sets 13 blue stars on a white background with blue and red stripes. A battle flag of that design flew at the head of General Nathaniel Greene’s troops when they defeated Cornwallis at Guildford Courthouse in North Carolina in March 1781, eight months before the British general ultimately surrendered at Yorktown. He has a copy of the Serapis flag that John Paul Jones hoisted above the British frigate Serapis after he brashly captured it off England’s Flamborough Head in 1779.

Kennedy’s passion for flags—in particular American flags and their British and Scottish forbears—goes back to 1958 when, on his last posting at Stewart Air Force Base (now Stewart International Airport), he went on leave with friends to East Poultney, Vermont. There, in an old inn he spotted a commemorative flag in the pattern of a Betsy Ross flag with an added 14th star, representing Vermont, which joined the original 13 in 1791.

Intrigued, he began collecting, flag by flag. While browsing around the village of Millbrook, he found one with holes at the folds, apparently nibbled by mice. But it had 37 stars, which would have placed it after the admission of Nebraska in 1867. “I asked the owner what he wanted for it,” he recalls. “He thought $25 should do it.” Deal!

When the Kennedys left the big old house in Millbrook and lost the display space his burgeoning collection required, he decided to donate them, choosing the Oklahoma Science Museum in his home state. All that remain are the replicas, plenty of photos (see gallery at www.thehudsonindependent.com) and a lot of historical knowledge. “History comes to life when you study something like this,” says the 84-year-old retired architect.

One question that lingers: was it indeed Betsy Ross who sewed that first flag, as is widely believed and taught? Kennedy has his doubts. “No provenance exists to confirm that hers, nor any other 13-star flag, was indeed the ‘first’ American flag,” he says. “While it is true that Betsy (nee Grissom) lived, was a seamstress and sewed flags, says Kennedy, “her own grandson, William Canby, admitted that he could find no official record identifying the maker of the first American flag. Canby admitted that he could find no official record identifying just who did make the first American flag,” says Kennedy. “Yet since he also found nothing to disprove that it was his grandmother’s, he decided to abide by the long-held family tradition that Betsy Ross deserved the honor. Whoever sewed those first stitches,” concludes Kennedy, “the flag itself remains a patriotic treasure.”

Looking back over the centuries of flag evolution since the revolution, Kennedy has come to appreciate what he calls the “genealogy” of the American flag. While living in London in the late seventies, he took note of the similarity of the hues of red and blue in both the British Union Jack and the Stars and Stripes. “Working backward in time via the British Navy, the 100-year combining of Scotland and England into Great Britain, and ultimately the St. George’s and St. Andrew’s flags identified that genealogy.” What he has yet to figure out, he admits, is, “How in the world did someone come up with the idea of having a cluster of stars in the upper left-hand corner and alternating stripes?”

Starting @ top left:

British Red Ensign became the Colonial British Flag (1600’s); Continental Colors (first flag under G Washington Jan 1, 1776);

Yellow Gasden Flag, Personal command flag of first Commodore of Colonial Navy, Esik Hopkins (1775); Rhode Island Regimental flag, gold stars (1775); Guilford Court House, Red white & blue! (1781) ; and hanging vertically, an 1840’s 13 star flag in the pattern designed by Francis Hopkinson, author of the first flag act (June 14, 1777).

@ Botton left:

Taunton (MA) flag with polite message(1774); First Navy Jack, note white border stripes (1775); Stark Flag: random pattern, Green field, 1777 (battle of Bennington) original canton in Bennington VT museum; Betsy Ross flag; Bennington Flag (ca 1801 based on fabric sample, also at Bennington museum; Serapis flag, one of the few flags for which we have provenance of it’s existence (1779); Alliance flag (the companion ship of J. P. Jones ship that captured HMS Serapis on September 23, 1779.