Ahead of elections, Town Board appointment raises questions about precedent, partisanship

Above, Ward 5 Councilperson Stephan Krakower thanks the Town Board for his appointment at the Oct. 21, 2020 Town Board meeting.

In the run-up to Election Day, Town of Poughkeepsie government officials had to make a decision without direct voter input: who to appoint to the Town Board seat vacated by Democratic Ward Five Councilperson Matt Woolever. The appointee would hold the position until Dec. 31, 2021. On Oct. 21, the Town Board voted 4-2 along party lines to appoint Stephan Krakower, a Republican who previously served as Ward 5 Councilperson for some 14 years. 

On Oct. 25, the Town of Poughkeepsie Democratic Committee released a statement which described the move as “a travesty and a violation of the civic rights of the voters of Ward 5.”

Woolever vacated his post on Aug. 31, 2020 when he and his family moved to Hyde Park. He was first elected to the seat in 2017, and was reelected in 2019 with 824 votes to his opponent’s 749. Krakower was first elected to the Town Board in 2000 and served consecutive two-year terms until he vacated his post in March 2015 after being appointed to the Town of Poughkeepsie Justice Court, which has two seats. He served as Town Justice from 2015 to 2019. He ran for reelection in Nov. 2019, but lost by just nine votes. 

During the Oct. 21 proceedings, Town Supervisor Jon Jay Baisley noted that although Krakower lost the judgeship, he was elected to represent Ward 5 on the Town Board every time he ran, sometimes by a large margin: In 2009, for instance, he won 756 votes to his Democratic opponent’s 532. He ran unopposed in 2011 and 2013. 

The Board’s two Democratic members, Sixth Ward Councilperson Ann Shershin and Third Ward Councilperson Jessica Lopez, voted against the motion because they believed the seat should be filled by another Democrat to reflect how Ward 5 voted in the 2019 election cycle. Lopez noted, “Stephan ran in a race for judge, not for this Fifth Ward seat, and the Fifth Ward did vote in favor of his Democratic colleague. So not only did the Fifth Ward vote pretty decisively for a Democrat to fill the Fifth Ward council seat, but also for Stephan Krakower specifically not to get his judge seat again.”

Republican members of the Board countered that the appointment was not a matter of partisan political gain, but of experience relative to the Democratic applicant, Christopher Parks. Parks, who has lived in Dutchess County since 1983 and in Ward 5 since 1999, has a Ph.D from University of California Berkeley in Physical Chemistry. He previously worked for IBM and volunteered for the Howland Cultural Center. Parks was invited to apply by the Town of Poughkeepsie Democratic Committee, and emphasized that his skill set would complement the Board. “There is urgent importance for the judiciary and public officials at all levels getting educated on what scientific societies such as the National Academy of Sciences have concluded about public issues,” Parks described in a later interview with The Miscellany News. Woolever shares an educational background in Chemistry. There are no requirements for serving on the Town Board other than being an adult who lives in the Ward they represent.

Republican members of the Board stated they were looking for someone with more governmental experience specifically. Ward 2 Councilperson Bill Carlos said in the Oct. 21 meeting, “When we’re making this kind of an appointment, we are voting to put somebody else in charge of the representation of 8,000 [or] 9,000 people. So when Stephan’s name came on, I knew that because he had done the job that he’s got the experience to be able to do it.” Ward 1 Councilperson Jeff Renihan similarly noted, “Some will say it’s about party affiliation. It has nothing to do with it. I looked at, faithfully, the resume itself.”

Baisley, who joined the Board as Councilman of Ward 1 in 2003, cited a longstanding professional relationship with Krakower as one reason he voted in favor of his appointment: “I have a very good working comfort zone with him, and that makes a big difference to me.” 

During his time on the Board, Krakower took an interest in balancing the Town’s budget, which is the highest in the county. He and the Board spearheaded the move from medical insurance being fully covered for Town employees—including Board members, who are paid approximately $9,000 per year—to paying a portion out of pocket. (The Town Supervisor makes just under $70,000, as the position is full-time.) He also worked to overhaul the Town’s computer system to a software that connects across departments. Today, he is involved in the Town as a local soccer coach and through his private law practice at The Krakower Law Firm, PLLC. His two children, ages nine and 13, attend the Spackenkill School District, from which Krakower graduated. 

“I grew up with the people who live here, the people who moved in and out,” Krakower said. “They’re my friends, family neighbors. I’ve always taken [office] as an opportunity to help, not Democrats or Republicans, but to help people.” 

Map of the Town of Poughkeepsie’s Wards. Courtesy of Dutchess County Board of Elections.

One among many

Krakower’s appointment is not the first time conversations about partisanship and representation have come to the fore at the Town and County level. 

Krakower was originally appointed as Town Justice in April 2015 after the retirement of former Justice Paul L. Banner, also a Republican, whose term was to expire on Dec. 31. The Town Board’s motion to appoint Krakower passed 5-1. “I found it a good opportunity to do something different…to figure out what justice means for each human being,” Krakower shared in an interview. Shershin, the lone Democrat on the Board at that time, was the sole nay vote. 

To fill Krakower’s unexpired Town Board position, the Board appointed Joe Lepore, also a Republican, who previously served on the Planning Board. During the April 8, 2015 proceedings, Shershin commented, “I’ve been approached by some constituents that were concerned that there was a mad rush to fill this seat and they would have rather seen a more open process.” Then-Town Supervisor Todd Tancredi replied that the need for Ward 5 representation was immediate. The motion to appoint Lepore carried 5-1, with Shershin again alone in opposition. Lepore was immediately sworn in, maintaining the Republican majority on the Board. 

That November, Krakower ran to retain his Town Justice seat and received the highest number of votes of the three candidates. He sat on the bench with Paul O. Sullivan, also a Republican, for a four year term. Lepore ran unopposed for the Ward 5 seat in Nov. 2015, but lost to Woolever, who earned 795 votes to Lepore’s 700, in Nov. 2017

In January 2017, the Town Board unanimously appointed Renihan to finish Baisley’s unexpired Ward 1 councilship. Baisley vacated the seat when he ran unopposed for Town Supervisor in 2016 to complete Tancredi’s term, which was to end in Dec. 2017. Renihan, who serves as a volunteer firefighter and Fire Chief, had never served in government before. The Town Association offers classes and webinars for new elected officials. These Board trainings, which the Town fully finances, occur throughout the year.

In both 2015 and 2020, local Democratic representatives pointed to what they believe to be a lack of transparency in the Town Board appointment process. The Democratic Committee’s Facebook statement, for one, states that the vacancy should have been advertised on the town website. Democratic Minority Leader of the Dutchess County Legislature and Vassar College Professor of History Rebecca Edwards similarly stated in an email correspondence, “Most residents of Ward 5 never knew there was a vacancy at all, much less that they could put in their names for consideration. That denies the public an opportunity to consider serving, and it gives the appearance of inside dealing.” 

The Town Board usually conducts searches to fill vacancies in-house, announcing vacancies at Town Board meetings and leaving the search up to the party committees, according to Baisley. The Board generally receives two to three applications. The procedure on how to fill vacant seats is not codified anywhere at the Town level. To Baisley, state-level guidelines are enough. He said in an interview with The Miscellany News, “I don’t think we should be told ‘who.’”   

Edwards noted that the Poughkeepsie Common Council conducted an open search for an applicant to fill a vacated Dutchess County Legislature seat, for which they interviewed 10 candidates. She and Lopez are examining the appointing guidelines in neighboring municipalities, perhaps to add to Poughkeepsie’s Town Code. “Are we ever going to see a world where a Republican majority appoints a Democrat or vice versa? Maybe not,” elaborated Lopez. “However, I do think there should be a better process in place.”

Neighboring towns, such as the Town of Clayton, post vacancies as well. Lopez further suggested that the Town advertise vacancies on social media, its website or in email blasts: “We send out emails about Halloween parades. Why can’t we send out emails about vacancies? Not only would that spur interest in applications, but more public input. More residents might come forward and say what they would like to see.”

Though there are few Town laws on how to appoint, Democratic representatives believe that the Republican majority set a precedent to maintain the party affiliation of the seat, which is reflected in their previous appointments’ outcomes and reasoning. On Oct. 17, 2018, the Town Board appointed Thomas Keith, a Republican who served on Spackenkill’s school board, to fill the vacated District 5 Legislature seat held by Republican Kenneth Roman. At the time, Woolever, Shershin and Lopez all favored Pam Kingsley, who ran against Roman for the seat. Lopez and Woolever argued that local politicians aren’t interchangeable simply by party affiliation, and that Kingsley had connected with voters in her candidacy; Shershin said Kingsley’s long-time attendance at legislature meetings meant she would be more prepared to “hit the ground running.” Carlson said, “In respect to the 1400 people who voted for him in that position, I think it’s incumbent upon us to try to at least match what Ken did in the legislature with the same kind of a person.” The vote was 4-3 along party lines. Keith remains in office today. 

According to Baisley, the Town Board works to keep partisanship out of the government. “We don’t use the party line,” he said. “At this level, the only people you have to answer to are the residents.”

Like Baisley, Lopez and Krakower noted that the Town Board is unanimous on most decisions. According to Lopez, though, some issues do break down along party lines. Lopez pointed to a recent example: She put forth a resolution to regulate contracts with individuals who have made large campaign contributions, which was voted down. Environmental policy, infrastructure and finance are other areas that Lopez cited as often breaking down along party lines. These issues are also discussed in committees, which contain a maximum of three members. The Town Supervisor, a position that has been held by Republicans since 2010, decides who sits on what committee—though, as Renihan noted, he willingly stepped down from the finance committee to make room for Lopez, who wished to bring Democratic representation. 

“The sentiment being echoed by the Republicans is fantastic, and it’s one I try to live and die by,” Lopez stated. “However I don’t think it’s fair to pick and choose when to decide that that is our method on the Town Board.” 

Tipping the balance 

Of its population of 44,062, the Town of Poughkeepsie has a total of 26,692 registered voters, including 10,962 Democrats, 6,345 Republicans and 7,391 affiliated with neither  party. The Town Board of seven has five Republicans and two Democrats. 

“It’s similar to the county, where there’s a preponderance of Democrats, but people running things have tended to be Republicans,” said Chair of the Town of Poughkeepsie Democratic Committee Kelly Lappan. This holds historically: In 2009, the Town Supervisor Patricia Myers was the only Democrat elected to the Board. In 2011, 2013 and 2015, Shershin was the only Democrat elected; in all three elections, five of the six elected Board Republicans ran unopposed. 

However, the balance tipped with Woolever’s and Lopez’s victories in 2017 and 2019, shifting the Board balance to 4-3 with a Republican majority, at least until Krakower’s appointment shifted the composition to 5-2. Lappan commented, “If the Republicans wanted to say even though there are more registered Democrats, they don’t seem engaged enough to come out and vote…I get that. But that happened already in Ward 5 several times recently, and those people voted for a Democrat.” The race for Ward 4 was also tight, with Cifone barely getting an edge—he won the seat by just 21 votes.

Lappan says the Democratic Committee hopes to bring more Democrats to office through a good slate of campaigns and candidates. “People are getting energized, I think, and so I’m hoping the energy from this year will carry over to next year,” Lappan remarked. The Republican Committee could not be reached for comment.

The next Town Board general election is slated for November 2021. Krakower stated he “fully intends on running”; Parks, too, is considering his options. For now, Krakower hopes to increase the Town’s recreational opportunities, which he believes are increasingly necessary with the ongoing pandemic. “We want to provide things that allow kids to have good healthy recreation and normalcy in their lives … We’re looking for positive development that’ll add good jobs,” he described.

Considerations of the future aside, the current Town Board is eager to govern together. “It’s over,” said Baisley. “They might’ve gotten a push from their party, we might’ve gotten a push from our party. It’s over. It’s time to go to work.”

For his part, Krakower said, “There are seven members of the Board, and I plan to work with all seven.”


  1. Great journalism. The approach seems to be bipartisan and the lesson seems to stress the importance of getting along in politics. I agree that open seats should be “advertised” and explained to public readers.

  2. In this historic election, and everyone after it, we must remember to vote down the ballot. Our local government does important work.

  3. I’m not surprised at there being so many appointments, but I am surprised that the same people are appointed this many different positions and that counts as experience. It’s like revolving doors. I can hardly blame them though because if I want to vote democrat, but there’s hardly any democrats running.

    I’ve never had any issues with any member of the Town Board. They’re wonderful people. as long as they care about the issues I care about (usually align with democrat’s platform but not always) then I feel represented. But there are serious concerns about how much our votes can really mean if we don’t have enough options or the person we vote for abandons the seat later, and we have no say.

  4. Does this town have any written protocol on filling a vacated seat on the town board other than the majority party picking a name that THEY feel is in the “Town’s” [their] best interests? The last thing us residents need is a costly lawsuit involving board members like what happened in the the Town of Putnam when Bill Carlos, then chief of police for the Town of Putnam Valley, dragged the Town of Putnam through costly litigation (see: — Carlos v. Santos, 123 F.3d 61 (2nd Cir. 1997).

  5. Does anyone have a copy of the scathing letter that was sent out to most local and state officials outlining many indiscretions within the Town of Poughkeepsie including police department & town board?

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