Crossing the Long Island Sound

Phil Reisman on the history and potential future of a Westchester-Long Island commuter path.

Forty-five years ago this month, Nelson Rockefeller was checkmated — and he knew it.

Without ceremony and betraying no trace of bitterness, the governor announced he no longer sought to build a 6.5-mile bridge across the Long Island Sound — a fabled stretch of rich-man’s water that Daniel Webster grandly called the American Mediterranean. Rockefeller’s surrender over the Rye-Oyster Bay span ended a bitter, politically complex battle stretching back to 1965.

The people had spoken; Rockefeller conceded — carefully omitting the fact that more than a few of “the people” were not as much altruistic environmentalists as they were wealthy Westchesterites and Long Islanders who had the wherewithal to scuttle the project.

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Some of the critics lived in the path of the bridge, on Rye’s Manursing Island, the site of three country clubs and a gated neighborhood where homes today sell for as much as $12 million. At the Long Island end lived Rockefeller’s sister, who quietly opposed the bridge: The span’s approach straddled her estate.

The Rye-Oyster Bay Bridge was the obsession of Robert Moses, the head of the Triborough Bridge and Tunnel Authority who dismissed his adversaries as “upstart mushroom aristocrats” and “snobs.” In the Rye-Oyster Bay saga, Moses is painted as a rapacious super-bureaucrat, a power-crazed villain whose aim was to build not merely one but many bridges across the Long Island Sound. “Moses would, if he had his way, cover the Sound with bridges as the Tiber was covered with the bridges of Rome,” Robert Caro wrote in his exhaustive study of Moses, The Power Broker.

Rockefeller enthusiastically shared Moses’ vision to build at least the one bridge.

A Sound-crossing of some kind has been sought with various degrees of seriousness since 1938. Think of it as the suburban equivalent of finding the Northwest Passage — a shortcut to save time, spur economic growth, and reduce congestion.

It is an idea that never dies. And it is back again — this time in the form of a tunnel, under the auspices of the current governor, Andrew Cuomo.

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Cuomo’s tunnel scheme is hardly new. Back in 2008, an ambitious Long Island developer by the name of Vincent Polimeni proposed a privately financed tunnel built with the help of the investment firm Bear Stearns. The Great Recession killed the tunnel, not to mention Bear Stearns.

Cuomo broached the tunnel idea in 2016, saying, “We have to think big.” But he took a significant step forward this year by commissioning a $5 million feasibility report that looked at three alternatives: a bridge from Winding River, Long Island, to New Haven; a bridge from Kings Park, LI, to Bridgeport; and a tunnel from Oyster Bay to Rye/Port Chester.

Read between the lines, and it’s clear that the tunnel is the preferred choice. It would cost up to $55.4 billion — that’s thinking big, all right. However, according to the feasibility study, a tunnel would avoid the environmental damage wrought by a bridge.

“We’re New Yorkers,” Cuomo once said. There’s nothing we can’t do.”

Oh yeah?

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Though Cuomo must be channeling his inner-Robert Moses, it’s very likely the feasibility study will wind up where all the Sound-crossing plans have gone — the circular file.

It will take at least five years just to get to the tunnel’s design stages. Undoubtedly, the project will be fought every step of the way. So far, not one Westchester politician has voiced support for the project.

Cuomo is nursing a lot of political headaches — among them a determined primary challenger and a New York City subway system sorely in need of financial support.

Assuming he remains in office long enough, Cuomo could end up in a multi-front war with two states, several towns, and possibly the federal government — which is exactly what happened to Nelson Rockefeller.

Rockefeller’s biographer, Richard Norton Smith, tells a story about how Rockefeller grew so frustrated during the Rye-Oyster Bay Bridge war that he struck state Assembly leader Stanley Steingut twice in the chest.

“You little son of a bitch,” Steingut raged. “I should really knock you on your ass!”

Cuomo may fancy himself a fighter, but he’s no Rocky.


The opinions and beliefs expressed by Phil Reisman are his alone and do not necessarily reflect those of Westchester Magazine’s editors and publishers. Tell us what you think: email

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