July / August 2026
The Reincarnations of WHEN AND IF
COURTESY OF ROLEX/ANDREA FRANCOLINI
WHEN AND IF, which takes the breezes of Buzzards Bay and Vineyard Sound in stride, is a 63’5” LOD schooner designed by John G. Alden for ocean passages envisioned by George Patton before he achieved fame as a four-star general during World War II. She was launched in 1939.
There is a small, faded photograph tacked to the wall at Ballentine’s Boat Shop in Cataumet, Massachusetts, on the Buzzards Bay shore of Cape Cod. It is covered with layers of wood dust, and the edges are a bit torn. The photo—small, grainy, and black-and-white, as if from an old postcard—captured a white-hulled schooner in light air, flying every sail she could without much to show for it. The photo is easy to overlook amid the maybe 75 on the wall. For more than a decade, I walked past the image daily—often more than once. But something about that schooner kept me looking again. Finally, my curiosity grew enough to dig out a magnifying glass with which I could barely make out her nameboard: WHEN AND IF.
The schooner, commissioned in 1939, had been the pride of George Patton Jr., the career U.S. Army officer who achieved fame as a World War II full general (see sidebar, page 41). He died after a motor-vehicle collision in Germany shortly after the war’s end without achieving his longtime dream of sailing around the world with his wife, Beatrice, and family. Before the war, Patton had made clear his wishes for the cherished schooner should he not survive the war: The family could keep her, donate her for educational purposes, or scuttle her. Beatrice chose to keep the schooner and sailed her extensively. After she died in 1953, the yacht passed to her brother, Fred Ayer, and later to his son, Fred Ayer Jr.
By the 1970s, the Ayer family was ready to find a new home for the schooner. Honoring the general’s wishes, they donated her in 1973 to Landmark School in Beverly, Massachusetts. The school, founded by Dr. Charles Drake two years earlier, provides students who have dyslexia and other language-based learning disabilities an academic approach tailored to their style of learning. The donation was a nod to Patton’s own history with the disorder. The school established a seamanship and character-building program built around the schooner. The costs of upkeep for WHEN AND IF and a second schooner acquired later eventually proved too burdensome, so the school ended its so-called Watermark Program in 1989. WHEN AND IF was again looking for a steward.
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