Greenwich, CT - Accountability And The American Ethos Gasping For One Last Breath.

What Political Ambiguity Looks Like From A Townie Of 50 years.

Greenwich CT is a town where affluence drips off the waterfront mansions and decorum appears to be valued more than accountability. Greenwich is a place where the privilege of old money intersects with the new-age political apathy of a community too busy protecting social status to bother with pesky concepts like honesty, character and genuine leadership. And beneath the gilded surface of Greenwich lies a simmering political war—one in which “Never Trump” Republicans have taken center stage, not by inspiring leadership, but by masterfully playing both sides to ensure that actual change remains as elusive as a yacht without a captain.

Let’s begin with Dan Quigley, the former chair of the Greenwich Republican Town Committee (RTC), whose tenure was the embodiment of the “Never Trump” ethos: moderation at all costs, even if it meant political stagnation. Installed in 2020 to keep Greenwich’s Republican Party “respectable,” Quigley was supposed to protect the town’s storied legacy of fiscal conservatism and Bush-era civility. Instead, his leadership became a case study in political paralysis. By 2022, he was unceremoniously ousted, replaced by a coalition of new faces rallying around the kind of grassroots energy Greenwich hadn’t seen since someone dared to put a non-hedge funder on the town council.

Under Quigley’s “leadership”, Greenwich Republicans did what they do best: avoid making waves. His most infamous moment came when he quietly banned Trump signs from RTC headquarters during the 2020 election, reasoning that associating local candidates with the sitting Republican president was just too risky. Of course, this decision was like blood in the water for Greenwich’s small but vocal pro-Trump contingent, led by figures like Carl Higbie, a Newsmax personality and Trump acolyte. Higbie slammed Quigley as a “squishy Republican” who embodied the town’s “Jeb Bush-style” establishment. It was the beginning of the end for Quigley’s grip on the RTC.

By 2022, Quigley and his moderate allies, including Fred Camillo and Ryan Fazio, found themselves overwhelmed by an insurgent faction of Republicans energized by frustration over Greenwich’s woke drift and Quigley’s failure to lead. Enter Beth MacGillivray, who had initially balked at political involvement, famously quipping, “It’s golf season, for God’s sake.” But her frustration with the “inactions” of Quigley’s RTC, combined with growing dissatisfaction over the town’s school policies and pandemic mandates, propelled her and others to power in what Quigley himself described as a “bloodbath.”

Quigley’s ousting marked the rise of a new RTC, one more aligned with grassroots activism and Trump-era populism than the genteel conservatism of Greenwich’s past. Yet the wounds from this political coup never fully healed. Figures like Fred Camillo and Ryan Fazio, nominal Republicans, have spent the last two years undermining this new energy, working behind the scenes to sideline conservatives like MacGillivray, Kim Fiorello, and others who dared to challenge the town’s elite consensus. And because misery love’s it’s own company both Fiorello and MacGillivray were handed their hats by the time the last election cycle was concluded. Fiorello quite literally was "run out of town” and Macgillvary retreated into the shadows and at what cost?

Camillo, for his part, has mastered the art of appeasement, publicly positioning himself as a unifier while privately leaning into the same optics-driven politics that defined Quigley’s tenure. His silence on key issues, such as federal funding strings attached to COVID mandates, speaks volumes. Similarly, Fazio, who brands himself as a pragmatic Republican, has been more interested in maintaining the good graces of Greenwich’s “Never Trump” elite than championing the interests of the town’s grassroots conservatives. Their strategy is clear: keep the RTC divided and ensure that anyone who deviates too far from the town’s polite norms is swiftly neutralized.

And then there’s Tina Courpas, the latest addition to Greenwich’s political landscape. Courpas was elected with promises of fresh leadership, yet her actions suggest a continuation of the same establishment playbook. My first hand experience with Courpus was cordial but standoffish and finally silent. Perhaps a consequence of learning about my affiliations with Fiorello but one can only speculate. If this is any indication on what is in store in terms of representation it it’s going to be another long two years. Khanna - the Demcorat incumbent who lost her seat to Courpas was at least honest about not really representing any Republicans. Courpas’s alignment with Camillo and Fazio and the “we’re not going to talk about or mention Donald Trump” ethos, signals that Greenwich’s Republican elite are more concerned with preserving their own social capital than supporting the kind of bold, grassroots-driven change that the town, and State for that matter, desperately needs and God forbid these people would actually do some goddamned representing instead of trying to score popularity and political points with the “don’t ask don’t tell” sycophants. It’s patently obvious and tiresome.

With Trump back in the White House, the political winds are shifting once again. Many of Greenwich’s “Never Trump” Republicans, who spent years distancing themselves from the former president, are now quietly rewriting their scripts. Camillo, who once seemed allergic to the idea of publicly associating with Trump, has begun to subtly signal his alignment with the new reality, dropping hints of support for America First policies in a bid to stay relevant. Fazio, too, has cautiously adjusted his tone, carefully navigating a political landscape where outright opposition to Trump is no longer tenable for Republicans hoping to survive primary challenges. And make no mistake THERE WILL BE CHALLENGES !

To understand why Greenwich’s Republicans have devolved into this perpetual cycle of infighting and inaction, one must look at the larger cultural dynamics at play. Greenwich’s wealth fosters a unique brand of apathy, where the stakes of political engagement feel abstract and the cost of challenging the status quo is uncomfortably personal. It’s not just about politics; it’s about cocktail party invitations, country club memberships, and maintaining one’s place in the social hierarchy. In this context, figures like Quigley, Camillo, and Courpas aren’t just politicians—they give the appearance of being gatekeepers of Greenwich’s elite bubble, where decorum is valued above actual representation.

It probably doesn’t help matters that some of the most powerful Democratic leaders in the state—Governor Ned Lamont, Senator Richard Blumenthal, and Congressman Jim Himes—all call Greenwich home. Their presence adds yet another layer of insulation for the establishment, creating an environment where bipartisan complacency thrives.

But that’s not all. There’s the media juggernaut of the Greenwich Free Press, Greenwich Sentinel, and The Greenwich Times, all working in careful coordination—or perhaps willful ignorance—to maintain the delicate facade of Greenwich’s political status quo. These outlets, often too cozy with the town’s elite, rarely challenge the entrenched power structures, opting instead to focus on feel-good stories and tepid critiques that avoid upsetting their readership or advertisers, donors et al. In doing so, they inadvertently (or intentionally) shield the very leaders who perpetuate the culture of apathy and inaction, leaving grassroots activists and dissenting voices struggling to break through the noise.

And the problem isn’t just cultural; it’s structural. The influx of federal dollars through programs like ARP ESSER, which tied school funding to mask mandates and vaccine promotion, which are clearly coming from Democrat fueled political paradigms has turned Greenwich’s institutions into extensions of the federal government. Let me explain.

Superintendent Toni Jones’s denial of these financial ties—despite clear evidence to the contrary—is emblematic of the town’s broader accountability crisis. Federal dollars have become both a carrot and a stick, incentivizing compliance while discouraging dissent.

And let’s not forget the role of Greenwich’s Democrats, who have skillfully leveraged the town’s shifting demographics to their advantage. Once a Republican stronghold, Greenwich is now a battleground where Democrats outnumber Republicans, and unaffiliated voters hold the balance of power. This political realignment has only exacerbated the divisions within the RTC, as “moderates” like Quigley and Camillo cling to the illusion that bipartisanship is still possible, while grassroots conservatives push for a more confrontational approach.

As Greenwich’s Republican Party teeters on the brink, the question for residents is clear: Will they continue to allow their leaders—on both sides of the aisle—to prioritize optics over substance, or will they demand REAL accountability? The stakes are high, not just for the town’s political future, but for its identity as a community because if things continue to drift in this direction Greenwich will have absolutely zero room or tolerance for any type of conservatism including but not limited to the type that has been trying to fend off the abhorrent brainwashing of children in schools with gender and the technicolor ideology that has been allowed to fester and grow in the town. How do we know ? Just look at the flag that’s flown in front if our town hall in the month of June that couldn’t represent anything more anti-American. And yet it gets placed right next to Old Glory. It’s tantamount to mockery really. And ALL of our political so called “leaders” won’t touch it with a 10 ft pole but they’ll put it up on a 30 ft one for all the entire town to see how we’ve capitulated and been quite literally been captured by an ideology so divisive it defies any logic why it’s allowed to have any kind of an audience.

In the end, Greenwich doesn’t need more politicians. What it needs are leaders willing to challenge the elite consensus, break free from the suffocating culture of decorum, and put the interests of residents above the social and financial incentives of the status quo. Whether that leadership will come from within the RTC or from a new, uncorrupted voice remains to be seen. For now, Greenwich remains a town at war with itself, trapped in the gilded cage of its own making.