Rye Mayoral Race: Henderson Leads in Fundraising, Spending

UPDATE: The McCabe campaign provided the following update to our story Tuesday morning: The $4,210 invoice was to MyRye.com LLC and not to the Rye Record (it was incorrectly recorded by the campaign and has been corrected). Also, the professional services of $4,000 was what McCabe “paid the lawyer who helped me win the Republicans attempt to knock me off the ballot” – Jeff Gasbarro, Esq.

The 32-Day Pre-General campaign finance filings submitted to the NY State Board of Elections on October 3, 2025 provide the clearest look yet at how Rye’s three competing slates are raising and spending money ahead of the November 4, 2025 election. All three committees show strong local donor support, but their spending patterns reveal differing campaign styles and strategic priorities.

The current filings are an update since the last filing deadline on July 11 (see GOP Candidate Bill Henderson Tops Fundraising in Mayoral Race) and show activity through September 29.

Here is what you need to know:

All In For Rye (Henderson)

Overview:
All In For Rye, the slate led by mayoral candidate Bill Henderson, reported the largest haul for the recent period. The committee disclosed approximately $25,049 in receipts and $18,778 in expenditures, with cash on hand comfortably above its rivals. Roughly 72 percent of its contributions came from Rye residents, underscoring a solid local fundraising base.

Top donors:
Henderson’s campaign benefited from a series of maximum or near-maximum gifts. $1,000+ contributions came from a dozen or more well-known Rye donors, including:

• Anthony Piscionere (local attorney, former local GOP head and father of Rye City Court Judge Taylor Piscionere) for $1,000; 
• Elaine DiConstanzo (former local GOP head and recent transplant to Boca Raton, Florida) and her husband Damian DiConstanzo, $1,000 each;
• Peter Duncan (CEO of George Comfort & Sons, a real estate firm whose holdings include the old Avon property (601 Midland Avenue) (now the NY Blood Center) and his wife Chris Duncan, for $1,000 each;
• A $2,000 transfer from a related entity, Bill Henderson for Rye, bolstered the total.

Spending:
The committee has been the most aggressive spender so far. Outlays included approximately $6,300 on online advertising with MyRye.com LLC, $4,810 on print ads in the Rye Record, and $5,500 to MP Thomas Consulting for campaign services. In addition, Anedot processing fees reflect a mix of small-dollar online giving.

Takeaway:
Henderson is using a well-funded war chest to lead local paid media while engaging professional consultants. The committee appears to be pursuing both air cover and precision outreach.

Learn more:

• Q&A with Mayoral Candidate Bill Henderson
• Q&A with City Council Candidate James Fee
• Q&A with City Council Candidate Robin Thrush Jovanovich
• Q&A with City Council Candidate Maria Tufvesson Shuck

McCabe for Rye

Overview:
Rick McCabe’s independent run for mayor raised $10,525 this period and spent $10,069, leaving little margin. Unlike its rivals, the campaign reported $6,675 in outstanding liabilities, all of it payable to McCabe himself. About 73 percent of its contributions came from Rye residents.

Top donors:
McCabe’s strongest supporters included:

• $1,000 from Kathleen McCabe
• $1,000 from Diana Page (president of Friends of Rye Town Park);
• $500 from former Rye City Councilmember Carolina Johnson
• $250 from the Committee to Elect Tommy Regan in Brewster.

Spending:
The campaign has balanced fundraising costs and voter outreach. Major expenses included $4,210 to the Rye Record (labeled as online advertising), $1,430 to In the Rye Media (print ads), and $1,396 to Fort Orange Press for printing services. Fundraising was a visible focus: $1,507 went to Rye Roadhouse for an event. Bookkeeping services with JMT Campaign Services cost $500.

Liabilities:
The most striking element of the filing is the $6,675 debt owed to the candidate, with memos citing “Professional Services” (~$4,000) and campaign mailings/office expenses. 

Takeaway:
McCabe’s campaign is competitive in donor support but financially lean, with liabilities casting uncertainty on its runway. The reliance on candidate-financed debt signals vulnerability if contributions do not increase in the final month.

Learn more:

• Q&A with Mayoral Candidate Rick McCabe

Nathan, Anderson, Kesavan & Ward for Rye

Overview:
The Democratic slate reported $12,667 in receipts and $8,045 in spending. About three-quarters of contributions came from Rye residents, and party committees provided meaningful support, including a $1,900 transfer from the Rye City Democratic Committee. The local Democratic Committee is not required to report on the same schedule, but maintains it has raised about $8,000 over the same period, and it is reasonable to assume at least some of those funds will be allocated to the current race.

Top donors:
The slate received:

• $1,000 check from Ellen Elsen, wife of Rye Record publisher Jon Elsen
• $1,000 checks from Cynthia Kuster, Maarten Kruijtzer, Rob Rubicco, and Melinda Stein
• Party support included $250 from the Eleanor Roosevelt Legacy Committee, and a $216.75 check and $1,900 transfer from the Rye City Democratic Committee.

Spending:
Expenditures reveal a lean but professional approach. The campaign paid $3,000 to MyRye.com LLC for online ads, $2,500 to Harrison David Brussel for campaign consulting, and $867 to Rose Press for campaign literature. Reimbursements to candidate Josh Nathan (~$897) and stipends to treasurer Raymond Sculky were clearly noted, alongside ActBlue and Stripe processing fees.

Takeaway:
This slate is running a disciplined operation with both grassroots fundraising and institutional Democratic Party backing. Its emphasis on digital ads, consulting, and literature suggests a focus on persuasion and turnout rather than event-driven fundraising.

Learn more:

• Q&A with Mayoral Candidate Josh Nathan
• Q&A with City Council Candidate Marion Anderson
• Q&A with City Council Candidate Amy Kesavan
• Q&A with City Council Candidate James Ward

Cross-Campaign Trends

Across the three slates, several patterns stand out:

• Local base: Roughly 72–75 percent of all contributions came from Rye/10580, showing that each campaign is primarily community-funded.
  
• Divergent strategies: Henderson leads in raw cash and media saturation; Nathan’s slate balances donor breadth with party infrastructure; McCabe shows strong donor loyalty but struggles with liabilities.
  
• Online vs. offline fundraising: Henderson (Anedot) and Nathan (ActBlue/Stripe) rely on digital pipelines, while McCabe shows heavier dependence on events and checks.

With one month until election day, Henderson’s All In For Rye enjoys the biggest financial edge, Nathan’s team benefits from party resources and steady donor backing, and McCabe’s campaign faces a test of whether it can overcome its debt load. The next filing—11-Day Pre-General—will show whether these trends accelerate or shift as the campaigns make their final push to Rye voters.

See The Numbers

• 2025-10-03 Rye Mayor Race Henderson All In For Rye Disclosure
• 2025-10-03 Rye Mayor Race McCabe for Rye Disclosure
• 2025-10-03 Rye Mayor Race Nathan Nathan Anderson Kesavan and Ward for Rye Disclosure
• 2025-10-03 Rye Candidates Final Summary (also see below)

This article was prepared with the assistance of artificial intelligence. We welcome your feedback.