For nearly a century, planners, politicians, and developers have dreamed of a bridge (or tunnel) connecting Connecticut and Long Island. The latest plan, led by Easton developer Stephen Shapiro, envisions a 14-mile bridge from Bridgeport, CT to Suffolk County, NY. Supporters say it could revolutionize regional transportation and generate billions in revenue, while critics warn of severe ecological disruption.

But before diving into today’s debate, it’s worth remembering: this is far from the first time the idea has surfaced — and history shows why it has repeatedly collapsed under the weight of lawsuits, politics, and environmental concerns.

The Modern Proposal: Promise and Peril

Shapiro argues his bridge could:

• Cut commuting time across the Sound to about 15 minutes
• Relieve traffic on I-95 and the Merritt Parkway
• Generate $8–10 billion in yearly revenue
• Slash carbon emissions by shortening car and truck routes
• Provide an evacuation lifeline for Long Island during emergencies

Yet environmentalists see danger signs.

Ecological Concerns

Noise pollution: Construction methods like pile driving generate underwater shockwaves that can injure or even kill marine life. The Atlantic sturgeon, an endangered species making a fragile comeback in the Sound, is particularly at risk.

Water quality: Runoff from cars could increase nitrogen levels in the Sound, undoing two decades of progress in reducing hypoxia (oxygen-depleted “dead zones”). Experts urge stormwater catch basins and filtration to mitigate the damage.

Bird impacts: Depending on design and lighting, the bridge could disorient or kill migratory birds, which are highly sensitive to artificial light during nocturnal flights.

Habitat disruption: Bridge abutments could create artificial “islands” that invite invasive species, alter currents, and displace native ecosystems.

Shapiro insists the disruption would be temporary and offset by long-term carbon savings, but marine scientists remain skeptical.

A Century of Failed Efforts

The Long Island Sound has a long history of ambitious, and often controversial, crossing proposals:

• 1938: U.S. Senator Royal Copeland floated an 18-mile bridge from Orient Point to New England.
• 1957: Engineer Charles Sells proposed bridges at Oyster Bay–Rye and Orient Point–Watch Hill.
• 1960s: Governor Nelson Rockefeller backed an Oyster Bay–Rye bridge. The project gained momentum thanks in part to the famed power broker Robert Moses, who envisioned it as part of his sweeping expressway system.
• Late 1960s/70s: Fierce local opposition, especially in Rye and Westchester, rallied against the project. Concerns about wetlands, neighborhood destruction, and pollution led to lawsuits. Courts ruled that the Triborough Bridge & Tunnel Authority, under Moses, lacked authority to build the bridge. The project collapsed.
• 1979: Governor Hugh Carey created a tri-state advisory committee, but nothing moved forward.
• 2000s–2020s: The idea resurfaced in Suffolk County master plans and even fictionalized in House of Cards. Each time, opposition and cost estimates — running into the tens of billions — killed momentum.

Robert Moses: The Bridge That Never Was

Robert Moses, the “master builder” of mid-20th-century New York, played a major role in keeping the dream alive during the 1960s. He pushed the Oyster Bay–Rye Bridge as a way to extend his expressway network and reduce pressure on city highways.

But unlike his triumphs in building bridges, parkways, and public works across New York, this time he lost. The bridge faced:

• Litigation: Courts ruled Moses’ TBTA lacked the authority to move forward.
• Local resistance: Residents feared destruction of wetlands, increased traffic, and disruption of shoreline communities.
• Environmental awakening: By the 1970s, laws like the National Environmental Policy Act (NEPA) forced large projects to pass rigorous ecological reviews, creating another layer of resistance Moses couldn’t bulldoze.
• Financial headwinds: Investors balked at the price tag, and the state pulled support.

The defeat marked one of the rare times Moses’ vision was checked — and a pivotal moment in the rise of environmental activism.

The Bridge Today: Déjà Vu All Over Again?

Shapiro’s pitch revives familiar promises: economic growth, traffic relief, cleaner air through shorter routes. And just like past proposals, it faces the same obstacles:

• Local and regional pushback
• Legal battles over jurisdiction and authority
• Environmental impact reviews that could take years
• Sky-high costs (estimates in the tens of billions)

The parallels to Moses’ failed Oyster Bay–Rye bridge are hard to ignore.

Can the Sound Handle It?

At its core, the debate raises one essential question: Can massive infrastructure coexist with one of the most fragile ecosystems in the Northeast?

Advocates see a bold investment in the region’s future. Critics see a repeat of history — a grandiose plan doomed by environmental, legal, and financial realities.

If the project ever moves forward, its fate will hinge on whether developers, scientists, and governments can design a bridge that not only connects two shores but also respects the water in between.

John Caravella Esq., is a construction attorney and formerly practicing project architect at The Law Office of John Caravella, P.C., representing architects, engineers, contractors, subcontractors, and owners in all phases of contract preparation, litigation, and arbitration across New York and Florida. He also serves as an arbitrator to the American Arbitration Association Construction Industry Panel. Mr. Caravella can be reached by email: John@LIConstructionLaw.com or (631) 608-1346.

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References:

• Greenwich Time – Shortcut or setback? Proposed bridge from CT to Long Island would risk Sound’s fragile ecosystem
• CT Insider – Same article, syndicated coverage
• Newsday – Long Island Sound connector concept revived in Suffolk master plan
• com – Crazy facts about the Long Island Bridge or Tunnel to Connecticut
• Wikipedia – Long Island Sound link(overview of bridge/tunnel proposals since the 1930s)
• com – Connecticut Roads: Long Island Sound Crossing(details on proposed crossings and why they failed)
• Untapped Cities – 7 Robert Moses projects that were never built(context on Moses’ involvement with the Oyster Bay–Rye Bridge)
• The Rye Record – Defeat of Builder Robert Moses and the Rye–Oyster Bay Bridge(local opposition and litigation background)
• Liquisearch – Long Island Sound Link, 1957 Plan
• Save the Sound – Advocacy and environmental monitoring(regional nonprofit frequently cited in ecological debates)
• EPA – Long Island Sound Nitrogen Reduction Progress
• NOAA – Atlantic Sturgeon Recovery and Conservation