June 18, 2026

SHAPIRO’S FOLLY – PART DEUX: THE BRIDGE THAT WON’T DIE

 

Connecticut: the land of steady habits where bad ideas don’t go away, they just get bigger.

Easton housing developer Stephen Shapiro is back again, expanding on his idea of a bridge across Long Island Sound from Bridgeport to Suffolk County NY.  Now he’s even added the idea of a tunnel for parts of the bridge, as shown in a fresh set of AI renderings, gobbled up by the media without asking many questions.

AI Rendering by Shapiro

Go big or go home, seems the theme, though the Shapiro ‘plan’ is just an amateur’s vision as Shapiro is neither a bridge engineer nor transportation planner.  He still thinks the 14 mile bridge / tunnel (or is it 18 miles, as he said this week?) can be built for about $50 billion.  But what do the experts think?

“Fifty billion dollars is a fantasy number,” says Pete Harrison of the widely respected tri-state Regional Plan Association which has been working in this field for over a century.  “The era of big bridge highways has passed.  But just imagine if that much money was spent on our trains and buses (in Connecticut),” he added.

What does CDOT think of Shapiro’s idea?  Not much.  “This proposal has never been vetted by CDOT or any transportation planning organization,” says CDOT’s Josh Morgan echoing Governor Lamont’s comments earlier this year. 

And the MTA (parent of Metro-North) is similarly uninspired.  “The cross-sound tunnel was not part of the agency’s 20 year plan,” Aaron Donovan told me.

One might guess that Shapiro thought he could win those agencies’ favor with his new design which adds a rail line down the middle of the bridge / tunnel.  Shapiro’s beautiful AI renderings show what looks like an Amtrak Acela hurtling across the bridge.  But elsewhere in his descriptions the train line is described as for “light rail”, which Amtrak and Metro-North certainly are not.

None of this bodes well for Shapiro or his political allies who promise to try again to find funding for a study.  The bill introduced this past session (HB-5320, which rightfully died in committee) called for a one year study of indeterminate cost.

That’s not realistic, one transportation insider-turned-consultant tells me: “A market / feasibility study would probably take about three years and cost $5-10 million.  An EIS (Environmental Impact Statement) would cost $25-50 million more.”

Is there even demand for such a crossing?  Shapiro guesstimates as many as 100,000 cars a day, each paying a one-way toll of $39.  For perspective, Fred Hall, the VP-GM of the cross-sound ferry from Bridgeport, carried only 525,000 vehicles in all of last year (at a toll for cars starting at $78 one way).  That means an average daily ferry load of 1400 vehicles. Would a bridge / tunnel toll of half that amount really mean more than 70 times as much traffic?

Most of the speakers at last week’s media event at the capitol spoke about how much Bridgeport would benefit from this new structure.  That city’s former mayor and State Senator Bill Finch (now a lobbyist for the electricians union) compared the project to putting a man on the moon.

Among the other speakers, a college student from Long Island who’d like a quicker ride home from school… a local disc jockey… and a state rep from West Haven hoping the crossing would bring Long Islanders to his town’s beaches. Not one of the speakers was a transportation expert.

Noticeably absent from the Shapiro cheering squad… anyone from Bridgeport city hall, the city most affected by such a scheme.

Why should we spend a single taxpayer dollar on a study that’s D.O.A. when we can’t even fund our existing transportation network properly?

This idea has been proposed and studied before… and never built, for good reasons.  Let’s keep that track record intact.

June 12, 2026

CONFESSIONS OF A KID WHO PLAYED WITH REAL TRAINS

I have a confession to make.

First, let me caution my readers that you should never, ever try this.  It’s dangerous and probably illegal.  But what did I know, a kid of maybe age ten, so fascinated with trains, that I did something this stupid?

I uncoupled a parked freight train on a siding. 

Yes, I crawled under a fence and went up to a stopped freight train maybe a half mile long, that I knew from experience would be parked there for a while.  I climbed up on the box car, turned wheels and pulled levers. I was having so much fun!

Then the train started up. 

I could hear the engine, far out of sight, blast its horn and slowly start tightening the slack between the railcars.  Jumping well off to the side I was amazed to see so much mass starting to move.  And then it happened.

As the cars tightened at their couplers I saw that one of those levers I had pulled had uncoupled the front of the train from the rear.  The last thing I remembered was a huge hose between the cars tightening and disconnecting with a loud “pop”.  More of a bang than a pop, but by that time I was running toward home.


The train seemed okay but as the front of the consist pulled, away the rear just sat there.  I assume that eventually, somewhere down the track they realized what had happened, maybe when the crew in the caboose (they still had them in those days) noticed they’d been left behind.

Pretty stupid thing to do, I’ll admit.  And dangerous too.  It took me weeks before I could even confess to my Mother what I’d done, and even then she thought it was just my imagination.  But it wasn’t.

But my ‘crime’ had given me a lesson about air brakes.  That hose, connecting each car to the next, was how the train’s brakes worked.

Brakemen at work

In the early days of railroading the brakemen literally were stationed atop the boxcars and, on signal from the locomotive crew blowing its whistle, they’d run across the cars tightening brake handles, hopefully stopping the entire train in time.

Then, in 1872 George Westinghouse (yes, the same guy who later brought us so many innovations in electricity) invented the automatic air brake.

All train cars’ brakes were connected to a hose-fed air pressure system controlled at the locomotive.  When the lines were pressurized, the brakes on all the cars would be released and the train could move along.  When it came time to stop, the pressure was slowly released and the brakes were automatically applied.

The system was also fail safe.  If the train started to derail (or was uncoupled by a naïve young rail fan), the pressure was cut and the brakes applied automatically just as I had witnessed. (I still wonder how the front of ‘my train’ kept moving after I’d popped the hose).

Westinghouse’s system worked so well that by 1900 air brakes were required on all trains.  And they’re still in use today.  That invention became WABTEC, the Westinghouse Air Brake Technologies Company, merging in 2019 with GE Transportation which makes locomotives.  Today WABTEC is a $45 billion company.  A spinoff, WABCO, put the same technology into trucks.

Stopping a huge train or a truck with just the power of air.  Quite an invention.

But a final word of caution from a once-stupid kid who should have known better: never, ever play with trains. Not stopped ones. Not parked ones.  Not “just for a minute.” They can move without warning, and one wrong step can be fatal.  So please…stay off the tracks.

June 05, 2026

CT TRANSPORTATION FIRSTS

I’m tired of people bad-mouthing Connecticut.

Yes, our taxes are high.  Yes, I-95 often feels like a rolling Town Meeting with brake lights.  And yes, Metro-North can still turn a simple trip into a test of faith.

But let’s give Connecticut some credit.  For almost 400 years, our small state has punched above its weight.  

Sure, we love our firsts. New Haven will always claim the hamburger at Louis’ Lunch.  Bridgeport gave Buckminster Fuller room to build his futuristic, three-wheeled Dymaxion Car, which looked like tomorrow until tomorrow changed its mind. 

Buckminster Fuller's Dymaxion

But let’s also consider Connecticut’s transportation history: a story of roads, wheels, rails, engines, submarines and aircraft.  It is also the story of a state that always wants to move faster.  Just look at our roads.

Before I-95, before the Merritt Parkway, before the toll debate that refuses to die, Connecticut had turnpikes.  In the 1790s, private companies built toll roads to connect towns, farms and ports. The idea was simple: better roads helped commerce. The second idea was more important: somebody had to pay for them, proving that some things never change.

Then came better road-building technology.  New Haven’s Eli Whitney Blake patented a stone-crushing machine in 1858, making crushed stone more practical for road construction.  Long before orange traffic barrels became our unofficial state flower, Connecticut was already trying to build better roads.

Then came bicycles.  Hartford became a national bicycle center in the late 1870s, when Albert Pope contracted with the Weed Sewing Machine Company to build Columbia high-wheel bicycles.  The bicycle was more than a toy.  It was personal mobility, freedom and an early argument for better roads.  Long before motorists demanded smooth pavement, cyclists were already lobbying for it.

The "Pope" Bicycle

Connecticut’s bicycle story didn’t end in Hartford.  In 1971, now-famous Cannondale was founded in Wilton.  It began by building camping gear and bike-towed trailers, not bicycles, later applying aluminum to sturdy but light-weight bike frames.

Or consider our trolleys.

Electric streetcars once linked cities, mill towns and neighborhoods across the state.  They let people live farther from work, shop beyond their own neighborhoods and travel without owning a car.  They stitched Connecticut together… before the automobile helped pull it apart.

Connecticut also got into cars early.  Hartford, Bridgeport and New Britain all had their moment in the auto industry.  But we also got into regulation early, because this is Connecticut and we do enjoy a good rule.  In 1901, Connecticut passed the nation’s first statewide motor-vehicle speed-limit law: 12 miles per hour in cities and 15 on country roads.

But transportation here was never just about roads.

David Bushnell of Saybrook developed the Revolutionary War submarine “Turtle”. That future eventually became Groton’s Electric Boat and the nuclear submarine age. Then look skyward: Pratt & Whitney made East Hartford synonymous with aircraft engines, while Igor Sikorsky made Stratford a helicopter capital.

So yes, we complain about traffic, late trains, fares, parking and the CDOT.  But Connecticut has never just watched transportation happen. We shaped it.

So be proud of our state the next time you’re stuck in the traffic our forefathers helped make possible.

 

SHAPIRO’S FOLLY – PART DEUX: THE BRIDGE THAT WON’T DIE

  Connecticut: the land of steady habits where bad ideas don’t go away, they just get bigger. Easton housing developer Stephen Shapiro is...