It was near the beginning of the now-infamous, closed-door meeting with Senate Democrats when it became clear that Gov. Ned Lamonts plan for 14 highway tolls was going to crash at the hands of his own political party.

The scene was Wednesday afternoon in the crowded third-floor Democratic caucus room of the ornate State Capitol, behind a pair of opaque glass doors and around a long table, with portraits of former Senate leaders on the walls.

The small room boiled over, with many among the 22-member caucus articulating long-simmering frustrations, both political and policy driven, with the first-term governor. Several senators were convinced they would lose re-election campaigns if they voted for tolls, even with an expected blue, anti-Trump wave next November.

Lamonts latest pitch for tolls, and the revenue generated by out-of-state cars, had quickly degenerated into a gripe session.

The multi-millionaire Greenwich businessman, who prefers penny loafers and an open collar to power suits, had failed a major test of his power, at the hands of fellow Democrats, in the rough-and-tumble of the intraparty politics.

The jaws of Lamont and his team, including Ryan Drajewicz, his usually steely, know-it-all chief of staff, literally dropped, according to people in the room.

The signature legislation of Lamonts first year in office, a 10-year, $21 billion infrastructure-renewal plan, including rebuilt bridges, wider highways and faster train service, was stalled on the tracks. While the meeting droned on for two hours, the damage was done early. At least one senator disrespected Lamont to his face.

The next day Republican senators offered a new plan, based on very optimistic borrowing rates, for $18 billion in infrastructure projects without tolls.

The anatomy of the collapse of the toll-centric plan has a lot to do with Lamonts inexperience in politics beyond the realm of affluent Greenwich, and his apparent inability to close a deal on a toll plan that a year ago, when he easily won his election, was going to charge trucks only for the use of state highways.

Amid concerns that courts could eventually rule against trucks-only, and the need for more revenue to tackle the states transit crisis, Lamont initially proposed about 50 toll gantries.

But as vocal opposition to tolls spawned fears in the Democratic majorities in the House and Senate, the number of gantries was drastically reduced and finally cut to 14 in the proposal that Lamont rolled out earlier this month, and calls CT2030.

Were not giving up on a solution, Max Reiss, Lamonts communications director, said Friday. Were also not going to give up on fiscal responsibility.

Sources with knowledge of the scene in the Senate caucus, who asked not to be identified, said Lamont has failed to build relationships with lawmakers. In this particular case, he hasnt held enough one-on-one discussions with individual legislators, a tried-and-true way to earn allies and possibly offer them benefits in exchange for support.

He has also offended many members of the General Assembly by holding up the annual legislative list of capital projects eligible for long-term bonding

Other say his privileged life and limited political experience beyond the Greenwich Board of Selectman and local finance board, might be hindering his ability to play political hardball.

I think he was trying to do the right thing, said Tom Swan, executive director of the Connecticut Citizen Action Group consumer-advocacy organization, who ran Lamont successful 2006 primary campaign against former U.S. Sen. Joe Lieberman. Swan said he was perplexed by the apparent implosion of Lamonts toll-centric plan. Its sort of amazing.

Swan said with the wide-ranging support of the southwestern Connecticut business community for the massive investments needed to free the region from gridlock and antiquated train lines, a failure of tolls as a revenue source would underscore the need for slightly higher personal income taxes on the states wealthiest, including Lamont and his neighbors in affluent towns.

Instead of highway user fees or increases in the sales tax or gas tax, an increase of less than a point on the top two tiers of income would still keep Connecticut below New York State, Swan said. Tolls are arguably the best way to help finance it, but the failure to address the policies could have a lasting impact on him and his administration. I hope he figures out over the next three years how to work more effectively with the legislature to drive a real progressive agenda.

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Anatomy of Lamont's failure to win on tolls - CT Insider