On a sun-splashed, blustery Tuesday in Seaside Park, Connecticut’s most scenic municipal landscape, an oceanic statue of showman P.T. Barnum who donated the land to the city peers out to Long Island Sound where developer Steve Shapiro pursues the attention of a self-proclaimed Barnumesque figure, President Donald Trump, to loan a project proposal $50 billion to build a 14-mile bridge connecting Bridgeport, and by extension Connecticut, to the north shore of Long Island, a move Shapiro says would reduce the drive time from three hours to 20 minutes and dramatically lighten traffic congestion along the Gold Coast of I-95.
The span would include a train deck while paying back the federal loan via toll revenue roughly bridging Bridgeport’s industrial West End shoreline to Smithtown, Long Island.
The 39-year-old Shapiro is no stranger to challenges. He’s the guy who has taken on wealthy Fairfield County suburbs, with restrictive zoning regulations, to build affordable and workforce housing units.
Barnum, in fact, was one of the originators of affordable housing, even serving as the bank for housing he built for arriving Europeans seeking a new way of life and jobs during America’s 19th Century Industrial Revolution, some of those innovative manufacturing companies settling in Bridgeport – sewing machines, machine tool, electrical, brass makers, luxury cars.
Shapiro is rallying support from government, political and business communities.
On Tuesday I conducted separate interviews, see above, with Shapiro’s vision as well as including former Democratic Mayor Bill Finch who now is an official with the International Brotherhood of Electrical Workers and Republican State Rep. Joe Hoxha, a community banker from Bristol, CT who knows something about financial deals.
Trump is no stranger to things Bridgeport. He was fond of revitalizing the city’s underutilized 70-acre peninsula Pleasure Beach in the early 1990s. In addition, as Connecticut was debating expansion of casino gaming, he purchased the vacant Jenkins Valve building at the junction of Downtown and South End, a five-acre site and reminder of the city’s industrial past, located off Interstate 95, as a prospective site for a gaming destination.
The Mashantucket casino was on line and Mohegan was just getting started.
The most high-powered gaming entities burrowed into Bridgeport but expansion required state approval.
I was a media and communications consultant to Trump at the time. He made things quite clear: if expansion happens I want it, If I can’t have it, I wanna kill. He feared expansion into wealthy Fairfield County, with him not involved, would cannibalize his Atlantic City interests.
In the end Fairfield County Gold Coast senators voted against expansion citing a host of concerns. In addition the state had an iron-clad monopoly agreement with the tribal nations. Any extra casino action had to include them.
Trump was pleased with the gaming outcome but not about paying roughly $300,000 a year in taxes for a property he no longer had development interest. “The assessment on this building is crazy,” he told me. “I’ve never seen anything like it.”
The site is now home of the city’s concert amphitheater.
So, Trump L.I Sound Bridge?
The president has a bunch of other developments carrying his name.
Why not?
ONLY IN BRIDGEPORT-January 14, 2026
A bridge between CT and NY? How many folks who reside in Bridgeport are aware about such long-term measures and despair that anyone routinely consults them with adequate advance notice, a simple rendition of the opportunity or concern, and specific benefits or cost to them?
Drones in Bridgeport are already here. With a nearly unanimous reaction to the process and protocol of a small room hosting two City Council committees causing ‘standing room only’ with no opportunity for the public thus assembled to utter a word about the subject: drones sought to improve public safety, funded likely entirely (as I did read the over 60 page agreement) by a State Grant of $500,000 for this specific Flock item @ $250,000 per year, with technology shared by the Police Department, Fire Department (and likely Emergency Services, as well) on land based and perhaps water based issues.
Where is space for an interested public to understand these issues, that include benefits, costs, and where the money is provided or lacking? Who plays that role, from the current Mayor’s project office staffers, who keeps track of such ideas, and keeps info fresh on the City website? Is it up to Lennie Grimaldi, a businessman extraordinaire, practicing journalism or elected and appointed City employees to do so officially?
With this Only in Bridgeport note, I am “Asking the Council” where the plan is, with a developed process for residents, and OPEN, ACCOUNTABLE, TRANSPARENT and HONEST values practiced? Are these values important to readers of OIB? Where are they in operation? Time will tell.
We can call it, The Donald Trump Memorial Bridgeport!
The Bridge is over:
https://youtu.be/r0Sy4twXSn0?si=4cc11yUVqoskYO6A