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Authors: Michael M. Thomas

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There are definite differences in social style between the two villages. People tend to characterize Leeward as “more Boston or Philadelphia” and Windward as “more New York,” and there’s some truth to that. The latter’s more aspirational, less inhibited about wealth and its uses. It was mostly Windward money that paid for the runway at the nearby mainland airport to be lengthened to accommodate large private jets. It was mainly Leeward
money that acquired and donated many of the larger tracts that make up Evangeline National Park.

A lack of pretension characterizes Leeward, what the sort of people who devour decorating magazines doubtless call “shabby elegance.” Newer money is expected to tiptoe into town and tug its forelock as it waits its turn for coffee or the newspaper or a table at Cain’s Lobster Pot, or for an invitation to play tennis or golf at the Viaduct Club, known to locals simply as “the club.” As one wag has put it, “Over at Leeward, they must have spent all of $100 in the last ten years fixing up the yacht club. At Windward they spend $100 on a cleat.”

Residents of both villages grumble about having to make concessions to an age when money has once again become the measure of all things, as it was back in the Gilded Age when wealthy folk first started to build their summer cottages hereabouts. Laying out a few million dollars for a fine property on either side of the bay is no assurance of immediate invitations to cocktails or dinner, or of membership in the Jug and Beaker, the exclusive local men’s club, although $100,000 to the local hospital might help.

At the seaward end of the narrow crescent harbor, at the bottom of the bluff, occupying several hundred feet of waterfront along the easternmost arc of Leeward Harbor where the land hooks sharply back, is the site of Hochster’s Boatyard. In the old days, the yard would be clanking, buzzing, busy, with one or two spanking new hulls ready to be masted and launched. Today, Hochster’s is padlocked shut, with shreds of wind-tattered legal notices affixed to the gate.

Around Leeward Harbor, “Hochster” is a name no longer honored; it has become an epithet that stands for betrayal and venality and “Judas money,” and on Saturday nights at the taverns where locals gather, an extra round often leads to declarations of violence and retribution against the family. No wonder Marina stays away.

If one turns left at the Hochster’s site and heads uphill in a generally northeast direction parallel to the shoreline, one soon enters the residential parts of Leeward Harbor. These lie on wide bluffland with good long views of the bay and its outlet to the Atlantic. They’re broken up by a web of narrow lanes signposted with the names of important residents—Longstreth, Anderson, Butler.

The longest of these pathways, stretching perhaps a quarter-mile from the main feeder road to the edge of the bluff, culminates in a white picket fence marking the turnoff into a short driveway. To the fence is affixed a wooden cutout of a nineteenth-century whaleboat that identifies the property as Longboat. This is the compound that for over a century has been the summer home of the Longstreth family. It comprises four buildings: a tall main house flanked helter-skelter by three smaller cottages. The oldest and grandest house, which gives its name to the compound and sits at the center of things like the manor on a feudal estate, was built in 1892 by Lucius Longstreth, great-grandfather of the present owner. The twin cottages named Moorings and Jibe Ho! were built in 1925, and the last and smallest, Gull’s Roost, in 1948, when Pilgrim Island was regaining its pre-Depression, prewar social rhythm and summer at Longboat had once again become a continuous merry parade of Longstreth family and friends.

The main house is the heart of the place: assembly point, command post, war room, hangout, sanctuary, bolt-hole—especially during the frenetic stretch from July 4 through Labor Day, when life becomes a blur of tennis, barbecues, golf, sailing, and croquet, all punctuated by the clink of ice in tall glasses and the chugging of Hochster harbor cruisers returning from excursions to the outer islands.

Longboat is a fine old shingled edifice, with spacious porches overlooking the harbor, and a number of commodious function rooms, including a country-formal dining room dominated on
one long wall by a large, especially fine Fitz Henry Lane painting, dated 1857, of
Leeward Harbor Seen from the Bluffs
. I’m told that museums in Portland and Boston are drooling over this picture, and I can see why.

In the middle of the house, off to the right of the stairs, overlooking the water, is everyone’s favorite room: a cozy, welcoming library that serves as a haven when autumn arrives earlier than wished or winter overstays its welcome.

There are two major family occasions on the Longboat calendar: the long Memorial Day weekend, when Longboat comes alive after its winter hibernation and the house is opened and made ready for the season, and, some twenty-odd weeks later, Labor Day weekend, when the compound is shut down for the winter. For an outsider to be included in one of these is a singular honor.

A few words about my host and hostess, B’s parents, Thayer and Marjorie Longstreth. They’re models—almost to the point of cliché—of a certain kind of New England distinction. Everything about them bespeaks long private and professional lives conducted with dedication, intelligence, and circumspection. True Yankee patricians: old names; old schools; old money, with family trees that boast bankers and merchants, parsons and schoolmasters. He can count Adamses, Cabots and Emersons on various branches of the family tree, as well as a mayor of Boston and a great-great-grandfather who died fighting at Gettysburg. He epitomizes a cultivated, tweedy, bow-tied, reticent style of getting and spending that’s become increasingly rare, limited to a number of shrinking habitats mostly in New England within an hour or so of Boston, around Philadelphia, and—although these now hover on the very brink of extinction—on the Upper East Side of Manhattan. In the summer, this old breed can be found on Boston’s North and South Shore, in one or two venues on Cape Cod, and in enclaves like Leeward Harbor or at Stockbridge and Lenox in the Berkshires.

Marjorie Longstreth, Thayer’s wife of forty-seven years, is tall and spare; at seventy-three, a handsome long-nosed woman, straight of carriage, with shoulder-length gray hair going white. Refined, precise, elegant, with a good sense of humor and a profound feeling for her fellow beings. After a brilliant four decades at Harvard Law School that culminated in a deanship and a chair in in Intellectual Property Law in her name, Marjorie retired from active teaching two years ago. But she has kept busy in retirement: she serves as a trustee and chief counsel ex officio to the Fogg and Gardner museums and the Children’s Hospital. Her résumé runs to thirty pages of positions held, honors received, committees and boards served on, not to mention innumerable articles, books, and distinguished visitor- and lectureships. Her 1987 book,
The Golden Brick Road: Gospels of Hope in American Politics
, was short-listed for the Pulitzer Prize, and her earlier book on
Roe v. Wade
remains the definitive text. During her time at Harvard, she got to know a young woman who is now the nation’s First Lady, with whom she keeps in discreet touch (the Longstreths dined privately with the First Couple last winter, and were seated with the presidential party at Senator Kennedy’s funeral in Boston).

It’s apparent at a glance that money has been neither a problem nor an obsession in this household. It may be that the absence of the former leads to a lack of the latter. Thayer retired as CEO of Back Bay Fidelity Trust, the final stage in the evolution of the old family bank, six years ago: well before, as he puts it, “all hell broke loose on Wall Street.” In 2002, wishing to assure himself and his family of greater liquidity, he sold the bank, which had been controlled by his family since the War of 1812, to Merrill Lynch for $800 million in shares. Of this sum, $260 million ended up in various Longstreth family accounts, with the balance going for taxes and to a family foundation that Thayer controls. That’s something B and I have in common; both our fathers’ banks—of
course her father
owned
his—were swallowed up by the Thundering Herd.

In 2003, barely a year after he sold the family bank to Merrill Lynch, a new man took over as Merrill’s CEO, an individual whose blinding arrogance, Thayer reckoned, would carry to certain ruin a firm that he had always considered one of the most prudent and collegial on Wall Street. He promptly sold the family’s Merrill Lynch stock, resigned his board seat, and urged various accounts over which he had influence to take their business elsewhere. We all know what happened to Merrill Lynch.

Since then, Thayer has busied himself with his trusts and clubs, with various civic, cultural, and charitable activities—and, above all, with Harvard, to which he has stayed deeply loyal, notwithstanding being outvoted on the Investment Committee in a bitter dispute with fellow committee member Harley Winters—yes,
that
Harley Winters—over a derivatives bait-and-switch that will end up costing Harvard nearly $1 billion to get out of.

Thayer is what he seems: a person of principle, common sense, and rockbound loyalty to family, schools, and country—the same qualities he displays in his supervision of the family office and its considerable assets, now lodged in the Boylston Street premises of a venerable Boston law firm. You’ll recall that, according to B, he’s been in a lousy mood all summer, although he seemed to be coming out of it this past weekend.

The Longstreth family’s feelings about Longboat are intense. The ancestor who built the house, Thayer’s great-grandfather, son of the Civil War hero, was in the Pierpont Morgan mold: a take-no-prisoners banker with an elaborated sense of noblesse oblige and a passion for music and art. He considered the material, environmental, and spiritual well-being of Leeward Harbor and its inhabitants to be his personal responsibility, and did his best to see that a similar sense of duty was inbred in his children and in
theirs. Among the locals, the Longstreths are spoken of with deference and affection, lords of the manor who are mindful of the responsibilities that go with privilege.

Marjorie, too, has been coming to Leeward as long as she can remember. Her father and
his
father, successive heads of a famous New England boarding school with strong church affiliations, served as seasonal rectors of the village’s nondenominational parish. With the exception of World War II, when gas rationing made the trip prohibitive and her family switched its base of summer operations to Boston’s South Shore, Marjorie’s long, happy girlhood summers were passed here, on the water and the tennis courts and at dances on the deck of the club, music provided by a borrowed Victrola, as she still calls a record player.

She made her debut here in 1958, at the Leeward Harbor Yacht Club, and was married at the club five years later. No less than her husband, Marjorie feels Leeward in her DNA, her marrow, her every fiber.

For me, being up there was bliss, like going back in time; it reminded me of the way, say, Bridgehampton used to be when I was a kid and my old man and I and another family shared a nice rented farmhouse for a couple of summers: simple, spacious, straightforward. No bullshit, no Ferraris, no clamor for restaurant tables.

It was interesting to talk to B’s old man about changes in the area, especially what’s happened to Hochster’s. He hates Harborside, the new condo development rising on the old boatyard site—largely, I suspect, because a principal investor in the development is his despised brother-in-law Walter Hardcastle.

People like the Longstreths were in a position to block the project for the usual historical preservation reasons, but unlike the preservation terrorists of the Hamptons, whose money and genealogies usually date back no further than a month or so, they chose to take a long view, and ask themselves, “If not Harborside, what
then? The boatyard isn’t coming back. Where will this village find work?” At the end of the day, the only solution seems to be the one every so-situated American community has come up with: tourism and servicing the new rich in ways that range from building and staffing McMansions to catering and serving elaborate picnics and clambakes. According to Marjorie, ten years ago there were two long-established realtors serving the Harbors; today there are a dozen, including local offices for big New York outfits like Sotheby’s.

For me, these are but zits on the face of perfection. I’ve come to think of Leeward Harbor and Longboat and the rest as B’s dowry, although only metaphorically, since it seems pretty clear that she has no intention of marrying me or anyone else, and I certainly have no immediate plans to marry.

Anyway, it was a marvelous four days. The Longstreths are great and gracious hosts. B’s mischievous twin Claudio and his companion Frederick were there, and I enjoyed them. B’s right about her brother’s politics: he’s as outspoken a liberal as I’ve run across in years; his faith in OG remains undimmed; any shortcomings are completely the fault of the GOP and its captive Supreme Court.

Unfortunately, there was one night when we were condemned to dinner at the Hardcastles’, a case of “having to fly the flag,” as Marjorie put it. Claudio refused to go, but as a houseguest I had no option. It was all very grand—caviar, ’82 first-growth claret (“96.3 in Parker,” as Walter Hardcastle told us); monumental flower arrangements by the florists who take care of La Grenouille in New York; a chef recently recruited from a three-star Paris restaurant.

I reminded our host that we’d met several years earlier at Rosenweis’s Christmas party at the Weir, but he drew a blank. He spent most of dinner telling the table about a book he’s planning to write, about “the goddamn ongoing niggerization of America and how are we going to stop it.” B says that if you want to see steam literally
blow out of someone’s ears, just say the name of our current president to her uncle. We were back at Longboat by 10:00 p.m.

Otherwise, the weekend was perfect—and if things between B and myself keep on as they have, there’ll be many more to look forward to. Great food and drink, great company, great weather. We picnicked, I was taken sailing, we hiked the national park trails, got in some downtime while the golfers golfed, and I loved every second. One day, Bianca and I took one of the little sailboats out and made for a small island that’s only clearly visible when the fog lifts. We anchored, waded ashore, spread out a picnic, then ate and drank and lazed in the chilly sun until a good idea struck us both simultaneously and we went behind a big boulder and made love, at a pitch of excitement that I thought might burst the laces of my boat shoes.

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