2026 New York General Election

Orange County 2026 election candidates, full ballot and voting guide

Anthony is running for Town of Chester Superintendent of Highways in 2026 on the Chester First line.

As of October 22, 2026, Anthony Riale did not have a website or any information online.

Transportation & Infrastructure

Anthony Riale

As of October 22, 2026, Anthony Riale’s website did not contain information on this issue.

Edward Krutsch

Buket Urgen

Chester isn’t just where I live - it’s where I grew up, where I learned the value of hard work, and where I’ve built my life. After more than 25 years of operating heavy equipment, solving problems, and leading others, I feel like everything I’ve learned along the way has prepared me for this role.

About Stephen

Those early experiences turned into more than 25 years of hands-on work. Over the last 25 years I’ve operated heavy equipment, maintained roadways, handled excavation, grading and drainage projects, plowed snow, and maintained and repaired equipment. I’ve also gained experience leading crews, managing projects, and budgeting.

Qualifications

Stephen Smith has operated heavy equipment and maintained roadways and equipment, including excavation, grading, drainage, and snow-plowing work. He has experience leading crews, managing projects, and budgeting.

I’m not a politician. I’m your neighbor. And right now, Chester needs truly independent leadership. As your Highway Superintendent, I’ll work respectfully with the Town Board while making my own decisions, speaking up when I disagree, and standing up for our Highway crew. My commitment is to you, our roads, and the department you depend on.

Plans to work with the Town Board while making independent decisions and advocating for the highway crew.

- Plans to work with the Town Board while making independent decisions and advocating for the highway crew.

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Stephen Smith

1. The Underlying Gender Discrimination Lawsuit
In the underlying lawsuit, Plaintiff brings two causes of action for gender discrimination in violation of the Equal Protection clause of the Fourteenth Amendment, as made actionable against Defendants by 42 U.S.C. § 1983. (See Compl. ¶¶ 44–45.) Each cause of action is predicated on Defendants’ treatment of Plaintiff as compared to their treatment of Plaintiff’s former male colleague, Walter Popailo (“Popailo”).

(See id.) Plaintiff’s first cause of action is based on her and Popailo’s allegedly comparable employment for the Town of Chester. Specifically, Plaintiff alleges that Defendants, who made hiring and compensation decisions for the Town, (id. ¶ 11), failed “to properly title, compensate[,] and employ” her in comparison to Popailo, despite the fact that she and Popailo held similar roles and responsibilities, (id. ¶ 44).

In June 2014, the Town Board appointed Popailo to the part-time position of “Parks and Recreation Director.” (Id. ¶ 13.)

Streichert v. Town of Chester, New York et al, 7:2019cv07133 - Document 39 (S.D.N.Y. 2021) :: Justia

In June 2014, the Town Board appointed Popailo to the part-time position of “Parks and Recreation Director.” (Id. ¶ 13.) In July 2014, the Town Board voted to make Plaintiff the Town’s full-time “recreation coordinator.” (Id. ¶ 14.) Six months later, Plaintiff alleges, the Town Board was paying Popailo an annual salary of $36,235.60, while only paying her an hourly wage of $23.99. (Id. ¶¶ 16–17.) Plaintiff also alleges that the Town Board “did not list her as having any title” at this time. (Id. ¶ 17.)

2 In June 2015, the Town Board made Popailo’s position a full-time role, (id. ¶ 18), and, in January 2016, confirmed that Popailo would serve as full-time “Director of Parks and Recreation” with an annual salary of $55,000, (id. ¶ 19); meanwhile, however, the Town Board listed Plaintiff merely as “Park & Recreation Streichert,” with an hourly wage of $28.66 per hour, (id. ¶ 21).

Walter M. Popailo previously worked for the Town of Chester as director of parks and recreation, including in both part-time and full-time roles.

Councilman (To Fill Vacancy)

  * Ryan Wensley (R, C, I)* - 1,851 (83.30 percent)
  * Walter Popailo (Chester First) - 367 (16.52 percent)

Chester Election Results | Daily Voice

Receiver of Taxes

Vincent A. Maniscalco, Republican, Conservative: 1,532 votes.

Karen Lopusnak, Democrat, GSM: 864 votes.

Walter M. Popailo, ORF: 47 votes.

Superintendent of Highways (To fill a vacancy)

John J. Reilly III, Republican, Conservative: 1,575 votes.

Goshen and Chester election results

Walter previously ran unsuccessfully for a council seat and for receiver of taxes.

Goshen and Chester election results - The Chronicle

As of October 22, 2026, Walter M. Popailo did not have a website or any information online.

Walter M. Popailo

As of October 22, 2026, Walter M. Popailo’s website did not contain information on this issue.

New York Superintendent of Highways, Chester (Orange County)

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Transportation & Infrastructure