Previously Published in The Messenger
By Matt Meduri
Suffolk County Clerk Vincent Puleo (R-Nesconset) is running for a second full term as the central records keeper of the County. He was set to face Anthony Portesy (D-Melville) this year.
Last Monday, Portesy abruptly quit the race. Portesy told Newsday last month that he was “in it to win it” and would resign his position as Chair of the Brookhaven Democratic Party and give up his six-figure job as Deputy General Counsel at Jake’s 58 Casino Hotel if he was victorious in November.
However, last week, Portesy’s job as well as dozens of political appointments at OTB were suddenly threatened. In addition, County Comptroller John Estreich (D-Dix Hills) was reportedly pressured to drop out of his race for the open seat against Brookhaven Highway Superintendent Dan Losquadro (R-Shoreham).
Portesy has reportedly been offered a Conservative line nomination for a judgeship. The deadline to fill a vacancy on the ballot after an already-nominated candidate withdraws is August 21.
Estreich remains in the race to succeed term-limited Comptroller John Kennedy (R-Nesconset). While some interpret the move as a GOP triage of their chances against what could be a
brutal environment this November, Estreich’s electability might be elevated for having stood up to political pressure.
Estreich had previously been tapped to face Senator Mario Mattera (R-St. James) in the Smithtown-Huntington-based Second State Senate District. That role now belongs to Harjot Singh (D-Dix Hills) (pictured right).
Estreich asserted his candidacy on social media after returning from military service.
“To quote Long Island’s own president, Teddy Roosevelt, ‘it takes more than that to kill a bull moose,” said Estreich.
Portesy has run for local office before. In 2019, he vied for the Brookhaven Highway Superintendent job against the aforementioned Losquadro. He lost that race 58%-41% as one of a trio of firebrand Democrats looking to challenge the status quo in Suffolk’s largest town. He ran alongside Dom Pascual (D-Farmingville) for Tax Receiver and Will Ferraro (D-Selden) for Town Supervisor. Both also lost their races that year.
There could be some weight to the theory of pressuring candidates to quit vital county-wide races. In 2025, several paper candidate Democrats who did not run active campaigns came relatively close in upsetting incumbent Republicans.
In the Fourth Legislative District of the Suffolk County Legislature (LD-04), which includes the Middle Country region, Legislator Nick Caracappa (C-Selden) held his seat by about 10 points over Nancy Silviero (D). Caracappa had never won any of his two full terms and his first special election with less than 60% of the vote.
In LD-06, which covers the northern half of Brookhaven, freshman Legislator Chad Lennon (C-Rocky Point) won by about 13 points over the inactive candidate Kevin O’Shaughnessy (D-Middle Island). He had cruised to victory in his first election in 2023.
In the Brookhaven Town Clerk’s race, Clerk Kevin LaValle (R-Port Jefferson), who won a special election for the post in early 2023, won by just under 10 points in solidly-red Brookhaven over Tricia Chiaramonte (D-Manorville), a perennial paper candidate who ran for Brookhaven Receiver of Taxes in 2023 and the Second District of the State Assembly in 2024.
But the shift could also very well be emblematic of the ongoing civil war within the Suffolk Democratic Party. Rank-and-file members have been furious with long-time Chairman and Babylon Town Supervisor Rich Schaffer (D-North Babylon) over refusing to allow grassroots and more progressive candidates into the local brand. Another one of their grievances is cross-endorsements with the Conservative Party and not putting up a candidate against District Attorney Ray Tierney (R) in 2025. Sheriff Errol Toulon (D) faced no Republican opponent, but was cross-endorsed by the Democrats and Conservatives.
Schaffer is facing a stiff internal challenge from Southold Democratic Committee Chairwoman Kathryn Casey Quigley (D-Southold). She’s pledged to tap into the progressive wings of the party that she thinks can revive the Democratic brand in Suffolk – a county where Democrats still hold a thin registration advantage over Republicans – and has pledged to end cross-endorsement deals.
“Since the day I started my campaign [for Suffolk Democratic Chair], I’ve been railing against backroom deals by party leaders,” said Quigley in a social media video, adding that those deals “hand seats to Republicans.”
Quigley accused Schaffer of ousting Portesy and Estreich.
“These candidates have been put in a horrible situation, having been told they will not be supported by [their] party leadership if they run,” said Quigley. “It is time for Schaffer to step aside.”
The Suffolk County Democratic Party did not respond to The Messenger’s request for comment.