The Story of the When & If:

When And If | Wiscasset Schoonerfest

Nearly everyone knows a little something about Wiscasset’s seafaring past.

There was a time in the 1800s when Wiscasset was second in importance only to Boston as a port of entry. At times there were so many ships anchored in the harbor, you could walk clear across the river on them—or so they used to say.

Shipbuilding was an important industry here as well. What you might not know is that this proud tradition was carried on well into the 20th century. Something else you might not know is that at least one of those Wiscasset-built schooners, the When and If, is still sailing the high seas.

The story begins a little over 70 years ago on January 6, 1938, when the F. F. Pendleton Boatyard —based in Wiscasset—contracted to custom build a 65-foot, 2-masted schooner. Although America was in the throes of the Depression, the small boatyard had stayed busy, employing 20 full-time craftsmen. We know for a fact from Louise Redonnett’s newspaper, The Town Crier, that in the spring of 1937 the Pendleton Boatyard was putting the finishing touches to three custom yachts in preparation for launching.

This new contract came from a self-avowed career military man named George Patton, later to gain fame as the charismatic Army general of World War II. All that was still some years away, however. In 1938, Colonel Patton, age 52, was the Commanding Officer at Fort Meyer, Virginia. Colonel Patton, it seems, had long dreamed of owning his own custom-built yacht. He chose veteran boatbuilder F. F. Pendleton of Wiscasset to build it on the recommendation of the yacht’s designer, John Alden. Alden, a naval architect, was renowned for his schooner designs and familiar with the Pendleton boat works. On January 6, 1938 the three men—Alden, Patton, and Pendleton—got together and entered into an agreement for Pendleton to build the schooner.

In 1981, I interviewed Fred Pendleton, F. F. Pendleton’s grandson and namesake, for a feature story I was writing for my newspaper, The Wiscasset Times. Fred Pendleton presently lives with his daughter, Nikki, on Fore Street. Their home overlooks White’s Island where the F. F. Pendleton Boatyard was once based.

During the interview, Fred Pendleton showed me the original typed contract signed by his grandfather, Alden, and Patton. He also had a ledger page showing the weekly payroll for the crew that built the When and If. The price for building the schooner was $31,700—a substantial sum of money—in installments of $6,340 each, to be paid at the completion of various stages of the yacht’s construction.

The schooner was launched a year later in 1939 and christened the When and If. The way Fred Pendleton remembered it, Patton named her that because when the next war was over, and if he survived, his dream was to sail his schooner around the world. As it turned out, the “if” part of the dream proved to be prophetic. General Patton, “Old Blood and Guts” as he was nicknamed, survived World War II but was killed shortly afterward in an automobile accident in Germany. The Portland Press Herald carried a story of General Patton’s death in its December 22, 1945 edition that included a picture of the When and If on the front page.

The Press Herald article quotes Fred’s grandfather, F. F. Pendleton, as saying, “General Patton thought the world of that boat I built for him. When the contract was made he [Patton] said, ‘I’ve got the money for her now and I’m going to plank it into her and then I’ll have her. Nobody knows what the value of money’s going to be later, but a boat’s a boat and if she’s bronzed-fastened she’s pretty nearly immortal.’” As we’ll see, that quote was to prove prophetic as well.

Fred Pendleton told me the When and If was the last “big” boat his grandfather built. “I was about 11 or 12 years old when they were building it. Maurice, my late brother, and I were both onboard her when she was launched. I can’t remember the exact date, but it must have been in the early spring or summer,” he said. “I remember the men saying Patton had enough champagne there to launch the ship!”

Fred said the hull of the When and If was originally painted black but later repainted white. “Its cabin had a lot of different kinds of wood, including teak and mahogany. The state room in the cabin was done in all blue leather.”

I had also interviewed Wiscasset’s longtime Harbormaster Jim Sutter for that same story. Jim told me he watched as the When and If was built. “I went aboard her right after she was launched and looked on as the men fitted her out.”

Jim told me he was about 19 at the time and clearly remembered some of the men who helped build the schooner. The late William Johnson of Wiscasset was one, he recalled. Two others were the father and son team of Vandel and Ed Gamage. “I remember watching Ed, high on top of the main mast, working on the rigging,” added Jim.

“The last time the When and If visited here during the summer of 1978, I went aboard her to look at the workmanship and to see how she was holding up,” Jim continued. “The finish work was probably the best you could get. The men who built her were all older craftsmen and quite experienced. To me, she looked as the day she was launched.”

By a strange twist of fate Jim Sutter would later serve in the U.S. Army under General Patton, and even met and shook hands with the famous commander. “I introduced myself and told him I was from Wiscasset and had been aboard his boat. That kind of surprised him,” Jim said. “As I recall, we were in Luxembourg at the time, during the Battle of the Bulge.”

The F. F. Pendleton Boatyard, long since gone, was located on the east side of White’s Island, which today remains privately owned, although no longer by the White family. A few rotting pilings and chunks of brick and bits of glass remain to show where the boathouse and mill once stood. The bricks are from the boiler’s chimney, used then to operate a steam- powered sawmill where wood for the ships was milled. Ages ago there was a small wooden bridge linking the north end of the island to Birch Point. The bridge has been gone for years but pilings are still visible at the low ebb to trace its route across the bay.

After Patton’s death, his schooner was sailed for a time by his wife, Beatrice Ayer Patton, who later gave the boat to her brother, Frederick Ayer. Ayer continued sailing the When and If for many years along the New England coast. In the 1970s the Ayer family donated the schooner to the Landmark School based at Prides Crossing, near Boston, Massachusetts. In the 1970s and 80s the Landmark School offered a summer seamanship program for dyslexic youngsters. General Patton was said to have struggled with dyslexia himself and would no doubt have approved of his schooner being sailed for that purpose.

The When and If, under the Landmark School’s ownership, made at least one visit to Wiscasset, her place of origin, during the 1980s. Michael Parker was the skipper, and at the time was compiling a history of the boat. The Landmark School continued its seafaring program through the 1980s. Then, in November, 1990 the schooner broke free from her mooring during a storm and landed on the rocks off the Town of Manchester-by-the-Sea in Massachusetts.

The schooner’s insurers initially declared the vessel a total loss and recommended scuttling her. Fortunately, a relative of the Ayer family came to the When and If’s rescue. Funds were raised and the schooner was eventually taken to the Gannon & Benjamin Boatyard at Martha’s Vineyard for repair. After two years she was relaunched in June 1994.