Suffolk Showdown: County Legislative, Law Enforcement Posts on Ballots This Election Day

Suffolk County District Attorney Tim Sini's office was part of a three-week investigation that led to the arrest of a couple linked to the overdose of a Riverhead man in April
Suffolk County District Attorney Tim Sini’s office was part of a three-week investigation that led to the arrest of a couple linked to the overdose of a Riverhead man in April

Voters will decide dozens of pivotal local races across the East End in the upcoming elections, including two Suffolk County legislative seats and a pair of key countywide law enforcement leadership posts.

Among the Hamptons and North Fork races to watch are Suffolk County Legislator Bridget Fleming (D-Noyac) running for re-election against Republican challenger Robert J. Carpenter III, and Suffolk Legislator Al Krupski (D-Cutchogue) in a rematch against GOP candidate Remy Bell. Topping the ticket will be Democratic Suffolk County District Attorney Timothy Sini facing GOP rival Raymond Tierney, a former federal and county prosecutor. And Democratic Suffolk Sheriff Errol Toulon has a challenge from Republican William Amato.

Also up this election cycle are all 18 county legislative seats and a plethora of town-level contests. Local judicial races will also be on ballots, but local Democratic and Republican leaders largely cross-endorse each other’s candidates in these races well before the elections, leaving voters no real choice other than a longshot write-in candidate. 


Krupski, the first farmer elected to the county legislature — he runs Krupski’s Pumpkin Farm in Cutchogue — draws on his decades of experience as a former Southold town trustee and board member as representative of the county’s first legislative district, which covers the North Fork.

As chair of the public works committee, he is running for his fourth full term after first winning his seat in a 2013 special election. Representing the legislature’s most rural district, his priorities include open space preservation, improving water quality, maintaining county services and protecting the region’s agricultural industry.

“Less than 2% of the population farms in this country, but you need to have that land available,” Krupski says. “We need to as a nation produce our own food, so we have our own food security, but it’s become more of a challenge as less and less people actually farm.”

Bell, a former Riverhead GOP chair, Suffolk Board of Elections clerk and perennial candidate who’s repeatedly challenged Krupski, among others, did not respond to requests for comment.

“The environment is the number one issue,” Bell told The Suffolk Times in 2015. “We also have to look at bringing better paying jobs to the North Fork and the entire legislative district so young people can stay here and afford to live here.”


Fleming, an ex-Manhattan prosecutor and former Southampton town board member who chairs the legislature’s powerful ways and means committee, is seeking a fourth term representing the second legislative district, which spans the South Fork.

She touts her efforts to replace outdated septic systems that contribute to harmful brown tides, increase public transportation options and manage the tick population as credentials she believes are reasons that voters should re-elect her.

“My primary focus for so many years has been on protecting and defending our natural environment,” says Fleming. “I will continue to work hard on the challenges that we’re facing because of climate change from both mitigating impacts with coastal resiliency … but then also doing what we can to prevent the increase of climate change [by] increasing our renewable energy portfolio.”

Fleming is also seeking the Democratic nomination in the 2022 race to replace U.S. Rep. Lee Zeldin (R-Shirley), who is likely vacating his congressional district representing the entire East End now that he’s the GOP frontrunner in next year’s gubernatorial race in which he’s seeking to oust Democratic Gov. Kathy Hochul. It’s Fleming’s second bid for Zeldin’s seat.

Carpenter did not respond to requests for comment.

The League of Women Voters of the Hamptons, Shelter Island and North Fork has scheduled a Zoom debate between Carpenter and Fleming for 7 p.m. October 18. It will also air on SEA-TV Southampton’s YouTube channel,

Ray Tierney held a press conference outside the Suffolk DA’s office in Hauppauge on September 8.
Ray Tierney held a press conference outside the Suffolk DA’s office in Hauppauge on September 8.


Sini, the county’s first-term district attorney who was elected with a mandate to reform the office as his predecessor Tom Spota was convicted of corruption, is seeking re-election against Tierney, a former prosecutor who questions if Sini is up for the job.

Sini is a former commissioner of the Suffolk County Police Department and ex-federal prosecutor who has overseen high-profile cases against the notoriously violent MS-13 street gang and the District Attorney’s East End Drug Task Force and launched the office’s first-ever conviction integrity bureau. But Tierney says Sini’s office blew a chance to arrest the alleged drug dealers accused of selling the fentanyl-laced cocaine that authorities blamed for causing a half dozen fatal overdoses on the North Fork this summer — arrests, Tierney argues, could have been made before the fatalities. 

“Tim Sini had at least four opportunities in the past 10 months to put [the suspected dealers] behind bars on felony charges and he failed to act,” Tierney told reporters during a news conference in September, arguing that authorities had probable cause to arrest the suspects before the overdoses.

Sini countered that Tierney is distorting the facts of the cases and blamed judges for rebuffing prosecutors’ requests to impose high bail that would have kept the suspects off of the streets prior to the overdoses. Tierney had also taken issue with New York State’s bail reform, which has resulted in some cases of recidivists committing additional offenses at a time when they would have previously been jailed pending trial on their initial charges.

“Our mission is to make our office a national model, to seek justice in every single case and to make Suffolk County as safe as possible,” Sini says. “We’ve accomplished all of this, despite the fact that we came into an office that was a mess, we saw the biggest change to criminal procedure law in a generation, and we had the pandemic. But despite these challenges, we’re getting the people’s work done.”


The district attorney’s race isn’t the only countywide law enforcement post with implications for the East End that will appear on ballots this fall: So is the Suffolk Sheriff’s seat, which is headquartered in Riverhead.

First-term Sheriff Toulon, the first Black man to lead the office, is a seasoned corrections professional who oversees the care and custody of hundreds of people incarcerated at county jails in Riverhead and Yaphank. His deputies and officers also carry out evictions, enforce court orders, and patrol courthouse grounds, among other duties. But managing the jail amid the COVID-19 pandemic has proven the biggest challenge of his term.

His opponent, Amato, could not be reached for comment and is reportedly not actively campaigning for office.

Election Day falls on November 2 this year and the early voting period runs from October 23–31.

To find your polling place, visit

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