Helen Rosenthal. (Photo: Facebook)

Helen Rosenthal, one of the leading Democrats campaigning for an Upper West Side Council district, cut a $1,000 check for former Republican Mayor Rudy Giuliani's aborted Senate campaign. But despite the neighborhood's status as a progressive bastion, Ms. Rosenthal's campaign told Politicker she stood by the contribution as a strategic play against a more conservative rival.

"As a Board member of NARAL Pro-Choice America, Helen donated to pro-choice candidates for elected office. In 2000, Giuliani ran against anti-choice Lazio in the primary and Helen donated to the pro-choice candidate who (at that time) was also anti-gun," said Ahmed Tigani, a spokesman for Ms. Rosenthal, in a statement. "Helen has always strongly supported Hillary Clinton and gave the maximum legal donations to both her Senate and Presidential campaigns."

Helen Rosenthal contributed to Mr. Giuliani's exploratory committee in February 2000, several months before he dropped his bid in May. Former Republican Congressman Rick Lazio would eventually replace Mr. Giuliani in the GOP primary and lose to Democrat Hillary Clinton.

Ms. Rosenthal, who has worked in several city administrations, including Mr. Giuliani's, did not give any money to Ms. Clinton's 2000 Senate campaign, according to FEC records. Ms. Clinton began laying the groundwork for a Senate race not long after Daniel Patrick Moynihan announced his retirement in 1998.

"I couldn't tell you why I didn't donate to Hillary Clinton [in 2000]," Ms. Rosenthal told Politicker in a follow-up interview. "It wasn't because I was fervently for or against anything. It had nothing to do with Clinton or Giuliani. It wasn’t purposeful or meaningful."

"I was a maxed-out person for Clinton for president," she added.

(Her spokesman further noted her contributions to "a broad array of progressive Democrats and organizations, including Congressman Jerry Nadler, Senator Kirsten Gillibrand, Gabby Giffords and NARAL.")

At the time, the Senate race was advertised as a high-profile battle between Mr. Giuliani and Ms. Clinton. According to reports, Mr. Lazio was "ambivalent" about entering the race and only officially jumped in after Mr. Giuliani dropped out. His entry into the race, according to 2000 reports, was not a surprise to the political establishment, however.

Ms. Rosenthal is facing a number of top-tier Democrats in her City Council race, including district leaders Marc Landis and Debra Cooper, businessman Ken Biberaj, former community board chair Mel Wymore and education activist Noah Gotbaum. The current councilwoman, Gale Brewer, is term-limited.

The Broadway Democrats. (Photo: broadwaydemocrats.org)

Members of the Broadway Democrats, one of the Upper West Side's most influential political clubs, are at odds over their endorsement of John Liu for mayor.

The club's endorsements process spun into minor chaos late last night when members were forced to complete their counting in the club's president's home. Then, early this morning, a member realized the club had miscounted the ballots because of a misinterpretation of the club's run-off procedures--forcing a re-count that gave the city's comptroller a victory.

"Some people are not accepting that and will be challenging that," said Curtis Arluck, the local assembly seat's male district leader, describing the fallout from the vote, which comes just over a week after Mr. Liu's former campaign treasurer and a top fundraiser were found guilty of campaign finance fraud.

The problems began around 10 p.m. when a longer-than-expected meeting forced club leadership to change locations and count the remaining ballots at club president Gretchen Borges' home.

During the club's first round of tallies, Mr. Liu received 31 votes, City Council Speaker Christine Quinn received 22, Mr. de Blasio 13 and former Comptroller Bill Thompson 4. Because no candidate received a majority, the club began an automatic run-off count, tallying voters' second and third-place choices to determine a victor.

But when the club was left with two finalists, City Council Speaker Christine and Mr. Liu, they stopped. Mr. Liu had the most, with 35 votes, but not the majority of the 71 cast he needed to win. The club determined it would make no endorsement for mayor in the race and members went to sleep.

But early in the morning, the clubs' Female District Leader, Liu supporter Paula Diamond Román, said she discovered they'd actually made a mistake. Per "Article VIII" of the club's constitution, the counters were supposed to have finished tallying up votes until they were left with a single candidate.

Members who were available--both Liu and non-Liu supporters--returned to Ms. Borges' house to continue counting. In the end, Mr. Liu came out with 42--or 59.2 percent. Of the 71 ballots, 29 offered no endorsement instead of choosing Ms. Quinn.

But the confusion left some members fuming and questioning whether the ballots could have been tampered with, leaders said.

"The process of having the votes here without anyone but me and the votes have left some people distraught that there’s an opportunity for mischief," said Ms. Borges, who said the district's assemblyman, Daniel O'Donnell, was especially upset.

But she and Ms. Diamond Román blamed the mix-up on innocent confusion over a new, complicated voting system that no one really understood.

"This is not our first choice of how this would have gone," she said.

Ms. Borges said she understood the concern from members and apologized for the snafu.

“It's not the deal way to do things. Yes, we should have known what we were doing before that night .... So there’s some culpability, no doubt about that."

Mr. Liu's campaign did not immediately respond to a request for comment.

Marc Landis. (Photo: Facebook)

When Marc Landis, a leading candidate to represent the Upper West Side in the City Council next year, talks about himself, he often boasts of his long record of fighting for affordable housing in New York City. The attorney and Democratic district leader, praised by his many endorsers for his tenant advocacy, also works closely with Tahl Propp Equities, a large real estate developer that has been sued by Manhattan tenants and accused of "predatory" financial practices in rapidly gentrifying Harlem.

"Tahl Propp was one of the early companies that we and other organizers spotted coming in and buying up large amounts of affordable housing and they weren't a known actor in the affordable housing or real estate world," said Emily Goldstein, coordinator of preservation and policy at Tenants and Neighbors, a statewide tenant advocacy group. "In more recent years, I know that they've said they care about affordable housing. They've said they care about the Harlem community. And yet their actual practices in many of these buildings have been detrimental to low and moderate income tenants, to the physical housing stock and arguably to the community."

Mr. Landis is the chair of the real estate department at the law firm Phillips Nizer, where he has worked in various capacities with the developer Tahl Propp Equities. Mr. Landis, who describes himself on his LinkedIn page as a "real estate and corporate transactional attorney focused on the acquisition, development and preservation of affordable housing," declined to speak on the record about his work with the company. But, according to a Tahl Propp attorney, Mr. Landis has collaborated extensively with the company.

"We continue to work with him on numerous types of deals and he's a great resource," said Neda Barzideh Levy, VP and general counsel at Tahl Propp, though she declined to specify the particular cases or instances to which Mr. Landis has lent his expertise.

The firm, according to tenant advocates, is a part of a new wave of real estate developers that, as private equity companies, buy up large chunks of affordable housing at speculative prices that realistically can't be supported by the low rent that tenants are paying, setting up a choice between attracting more affluent tenants to the buildings or running into financial trouble as debt piles up.

Indeed, Tahl Propp, which owns more than 3,000 apartments across the city, has repeatedly clashed with Harlem tenants over the last decade. A 2008 report detailed the plight of several buildings in Harlem that Tahl Propp purchased, describing how the company would, according to residents, cut back on maintenance repairs to increase profit margins and force lower-income residents away, thus creating vacancies for market-rate apartments. For example, Tahl Propp pulled one building at 1900 Lexington Ave. from the state's Mitchell-Lama program, which provides affordable rental and cooperative housing to moderate and middle-income families. A resident of that building, Alvin Johnson, founded Harlem Tenants Against Tahl Propp even before that happened.

"They come in and they buy up Section 8 buildings, former Mitchell-Lamas, and they take buildings out of the Mitchell-Lama program triggering these high, exorbitant rents," Mr. Johnson told Politicker, referring to buildings where low-income tenants receive federal vouchers to help pay their rent. "Or they put pressure in the Section 8 building. They enter into these agreements with the government where the government pays them rent that is so ridiculous that the government is actually running out of money ... with their rent-stabilized buildings, they look to convert them all to co-ops and condos."

In 2010, Tahl Propp further settled a $3 million lawsuit at the Normandie, a building at West 119th Street, which the company converted from rentals to condos in 2005. Residents complained that the building had exposed structural beams and pipes, cracked hardwood floors and various other maladies. A year later, the Department of Housing Preservation and Development took Tahl Propp to court amid allegations that tenants were denied heat and hot water in one of Tahl Propp's newer condo conversions in Harlem. Tahl Propp, according to HPD, paid $1,000 in penalties and corrected the issues. Last year, Tahl Propp faced litigation from its own investors.

Although activists like Mr. Johnson describe the company's efforts to keep housing affordable as halfhearted at best and nonexistent at worst, a company spokeswoman contested any claims that the company isn't completely committed to building and maintaining affordable housing. She said the company, in addition to donating school supplies and toys to Harlem children, is now building two low-income housing developments and has received top quality of life scores from the U.S. Department of Housing and Urban Development.

"They are committed 150 percent to affordable housing," said the spokeswoman, Linda Alexander. "They've spent literally hundreds of thousands of dollars in the community."

For their part, Mr. Landis' campaign was happy to talk about the candidate's other work on affordable housing issues, like organizing tenant associations at three Upper West Side buildings, leading lobbying trips to Albany on behalf of tenants' rights and filing a suit against Fannie Mae to force the lender to provide emergency repairs to apartment buildings.

Mr. Landis is running to take over from term-limited City Councilwoman Gale Brewer against a crowded field that includes Helen Rosenthal, Mel Wymore, Ken Biberaj, Debra Cooper, Noah Gotbaum and Thomas Siracuse.

(Photo: Facebook)

In one of its first endorsements this year, the influential 1199 SEIU United Healthcare Workers union has backed District Leader Marc Landis to replace outgoing Upper West Side Councilwoman Gale Brewer. The race to replace Ms. Brewer is one of the most hotly contested in the city, so the backing from one of the state's labor powerhouses is undoubtedly a nice boost for Mr. Landis' campaign.

"Marc Landis has a proven record as a progressive activist dedicated to improving our public schools, creating good jobs, advocating for affordable health care and protecting affordable housing for the working families of New York City," George Gresham, the union's president, said in a statement. "As a Democratic party official and through his pro bono legal work he has shown the promise to be a City Council representative who will always stand up for the Upper West Side community and the city," Mr. Gresham added.

As is the case for many of the city's open Council seats, there is a crowded field of candidates to succeed Ms. Brewer. Joining Mr. Landis in the race are former Community Board 7 chairs Mel Wymore and Helen Rosenthal, Democratic State Committeewoman Debra Cooper and businessman Ken Biberaj, all of whom have been raising money at a healthy pace.

The campaign is likely to be a fun one. Mr. Wymore hopes to make history as New York City's first transgendered elected official, for example, while Mr. Biberaj was mostly recently found successfully fixing a typo in a street sign named after Thelonious Monk.

Ms. Brewer, who is term-limited out of seeking reelection, had expressed interest in campaigning for Manhattan Borough President but has been fairly quiet about her intentions in recent months.

Ken Biberaj (Photo: Facebook)

Ken Biberaj, a vice president at the iconic Russian Tea Room restaurant, has hired a big name to work on his City Council campaign: veteran political consultant Hank Sheinkopf. Mr. Biberaj is running to replace term-limited incumbent Councilwoman Gale Brewer.

“As an Upper West Sider myself, I’m thrilled to work with a candidate who has such a compelling vision for the neighborhood’s future,” Mr. Sheinkopf said in a statement this morning. “It is important that we help protect small businesses and young families on the West Side, and I look forward to representing such a strong and motivated candidate as Mr. Biberaj.”

“We are putting together a strong team of both professionals and volunteers to have a first rate campaign," Mr. Biberaj said in the same statement. "I know Mr. Sheinkopf and his company will be instrumental in helping us do just that.”

Like many open council districts in 2013, the campaign to replace Ms. Brewer will be highly spirited one. District Leader Marc Landis, Helen Rosenthal, the former Chair of Community Board 7, and Mel Wymore, the former Chair on CB7, have all announced their campaigns and more candidates may still yet enter.

Gale Brewer (Photo: Facebook)

Veteran Upper West Side Councilwoman Gale Brewer is jumping into the race for Manhattan Borough President.

"I'm going to definitely do it I. haven't gotten myself organized, because I'm working on so many different issues, but I will," Ms. Brewer told The Politicker last night at a public forum hosted by Police Reform Organizing Project at the LGBT Community Center.

Ms. Brewer is entering a crowded field. With current Borough President Scott Stringer gearing up to run for mayor next year, Councilman Robert Jackson, Community Board 1 Chair Julie Menin and Councilwoman Jessica Lappin have all already begun campaigning for the position. 

Ms. Brewer, who's been in the City Council since 2002, said she'd love to remain in that role, but term limits forced her to make a move.

"I think, to be very honest with you, I would love to stay where I am. I love my neighborhood, but it's term limits, I got 12 years and I've enjoyed every minute of it," Ms. Brewer said. "I do love my borough and I think there's still projects to work on right now. I'm working on retail, paid sick time, open data. Should I go on? You know, a lot of different things."

Prior to entering the City Council, Ms. Brewer worked in the nonprofit sector and in a variety of political positions including; Deputy Public Advocate for Intergovernmental Affairs, director of the Mayor's Federal Office in New York City and as chief of staff to former Councilwoman Ruth Messinger. Ms. Brewer said she thinks her experience sets her apart from the other candidates planning to run for Manhattan Borough President.

"I think I have this amazing long history. I mean, I've worked all the way back to John Lindsay, so I have worked on non-profit sector, affordable housing, education," Ms. Brewer said. "There's nothing that I haven't really worked on and I think that's what I bring to the table, a wide knowledge of many different issues."

Ms. Brewer is confident about her chances.

"I'm always optimistic. I have a great district and I've been working on all these different issues from women to affordable development for a very long time," she said. "So, I think I just bring a long history and, in the last twelve years, I've been able to pass legislation I think helps people. It's something that I'd love to do on a larger scale, but I do love my neighborhood ."

Ken Biberaj (Photo: Facebook)

Ken Biberaj, who works as Vice President at the Russian Tea Room restaurant in Manhattan, looks like he might be throwing his hat in the ring to succeed term-limited Councilwoman Gale Brewer. This afternoon, he registered a committee for the seat, allowing him to fundraise and campaign for the City Council position in 2013.

Mr. Biberaj came to his executive position at the iconic restaurant through his family's real estate business. The Russian Tea Room has often been featured in pop culture, making appearances in shows ranging from When Harry Met Sally to Gossip Girl.

In addition to his business background, Mr. Biberaj has also worked for political campaigns in the past. He was, among other things, the Florida Research Director for the Kerry-Edwards for President Campaign in 2004.

Mr. Biberaj will face a crowded field in the Democratic primary. Candidates already running include District Leader Marc Landis, Helen Rosenthal, the former Chair of Community Board 7, and Mel Wymore, the former Chair on CB7.

Update: Mr. Biberaj passes along a statement confirming his intentions to run for the City Council:

"As an Upper West Sider and a member of a small family-owned business, I am running for the 6th Council District because we need someone with outside experience who understands our community and how small businesses work. The West Side is one of the best places in America to live and raise a family, and I pledge to fight for the qualities that make this neighborhood so great.”

Mel Wymore

At his first meeting after being elected chair of Community Board 7 on the Upper West Side, Mel Wymore had quite an announcement to make: he was no longer a woman.

Prior to declaring his new gender in April 2010, Mr. Wymore spent more than a decade serving on the community board. He realized he wanted to become a man about a month before taking the chairmanship.

“I’ve held many roles on the community board, however always in the role of a woman,” Mr. Wymore told The Observer. “I knew that I was going to be changing very overtly in front of everybody when I was elected, so on my very first meeting as chair, I announced to the community board that I would be transitioning and that they could expect changes. At the time, I said I would maintain the female pronoun until I announced otherwise and that if anyone had questions please don’t be afraid to ask me directly.”

After his term on the community board ended, Mr. Wymore launched a 2013 campaign for the District 6 City Council seat. If his council bid is successful, he would be New York’s first transgender public elected official. Though Mr. Wymore doesn’t shy away from discussing his gender identity, he doesn’t want to be pigeonholed as a “novelty candidate.”

“Look, I’m the qualified candidate here, but I happen to be transgender,” Mr. Wymore explained. “I do realize, however, that I’m an exemplar of a certain kind of difference that’s in a very small minority, so recognizing that, I have a particular responsibility and a voice to speak about difference and inclusion.”

For Mr. Wymore, the road to the Upper West Side began in Arizona. His father, A. Wayne Wymore, was a professor at the University of Arizona and a pioneer in the discipline of systems engineering. Mr. Wymore eventually followed his father into the profession, which has defined his approach to politics.

“Engineering is a discipline of thinking,” Mr. Wymore said. “So, for example, in any given problem you can put on a band aid, or you can look at what caused that wound so you can shift the system that caused that problem at the same time that you’re making sure the bleeding stops. Systems engineers are trained to do that and I think that’s one of my biggest assets.”

This focus on identifying root causes means Mr. Wymore, according to him, is constantly seeking ways to improve and streamline the workings of local government while simultaneously tending to day-to-day business. He believes this is especially important on the Upper West Side, which he describes as an ideal place to pioneer new initiatives and programs due to the upscale demographic of the neighborhood.

“There’s a lot of opportunity, especially at local levels of governance, to really forge new models for working together, and solving problems and creating vision,” Mr. Wymore said. “The Upper West Side is uniquely positioned to be a paragon of urban living in that we’re a very successful, dense population and we can together decide what we want to look like in the future in terms of sustainability, and education, and housing, and health care, and taking care of older people and taking care of younger people. We have real opportunities because we are so successful.”

Growing up as the child of an academic also meant a nontraditional upbringing for Mr. Wymore that included extended stays in Hawaii, Austria, China and Costa Rica, where Mr. Wymore said he was enrolled in a local public school despite speaking no Spanish.

“I got shipped into the local high school where no one spoke English and I had extremely blond hair. I was literally the only Caucasian there,” Mr. Wymore said. “That was a real novelty for all the other kids, I guess, at that point. I kind of learned what it was to be the only one—to be different.”

As a child, Mr. Wymore said he suppressed his desire to be male.

“I so wanted to be a boy when I was a little kid—so desperately wanted to be a boy, and then when puberty rolled around, I kind of buried it,” Mr. Wymore said. “I think between hormones and peer pressure and cultural expectations, I just kind of said, ‘O.K., I’ve got to kind of get with the program and be female.’”

Love eventually brought Mr. Wymore to New York City during his mid-20s.

“I’ve almost lived half my life here now,” Mr. Wymore said. “I was in a long-distance relationship and we finally decided it was time to co-locate, so we said whoever got a job first, that’s where we would move. And he got a job here in New York City, so I moved to New York City and we started a family.”

Mr. Wymore said he’s still “very friendly” with his ex-husband and they share custody of two children, but the marriage didn’t last.

“It was a straight family, a conventional marriage, I guess is the way to say it,” Mr. Wymore said. “I was very depressed and couldn’t really figure out why that was and kind of finally came to discover that perhaps it was a sexual orientation issue, so I came out and we divorced.”

After the marriage ended, Mr. Wymore said he “began life as an out lesbian mom,” but something was still missing.

The realization came when Mr. Wymore attended a class on gender offered to parents at Fieldston, his children’s high school. The class was hosted by the YES Institute, a group dedicated to promoting discussion of the issues surrounding gender and sexual orientation. Mr. Wymore was so affected by the class that he subsequently took courses at the institute’s headquarters in Florida where he realized it was time to make the transition.

“Before the realization of being transgender, some people explain that experience as going through life in a gorilla suit and that’s actually very poignant. It works as an analogy for me,” Mr. Wymore said. “For me, it was like a bird out of a cage—just complete freedom and joy around having finally, after all those years, discovered kind of what that gorilla suit really was made of and being able to just rip it off.”

Now, Mr. Wymore said he identifies as a transgender person rather than belonging to either of the two traditional genders.

“Sometimes I feel very feminine, sometimes I feel very masculine. I more often feel masculine than feminine, so I kind of identify as transgender,” Mr. Wymore said.

Though he hopes we one day live in a world without a binary gender model, for now Mr. Wymore is asserting his male identity because he sees it as an opportunity to raise awareness.

“I have chosen to select the ‘M’ on the passport application because there isn’t a ‘T’ available and because I think the ‘M’ is more consistent with how I want to be read, but also more of an opportunity for education.”

His race for the City Council will be an uphill battle. Mr. Wymore is hoping to replace Gale Brewer, who is retiring after more than a decade and the lack of an incumbent in such a high-profile district is expected to lead to a hotly contested campaign. For her part, Councilwoman Brewer said it’s far too early for her to make an endorsement or guess at Mr. Wymore’s chances, but after working with him for many years through the community board, she praised his analytical approach to local politics.

“He’s a data person,” Councilwoman Brewer told The Observer. “He loves data and that’s a great perspective to have.”

The race may be more than a year away and the field isn’t entirely clear, but Mr. Wymore said he’s optimistic about his chances.

“I do think it’s very possible I could win because I’ve put in the time,” Mr. Wymore said. “Not just put in the time, I’ve produced real results for people and I am coming from a different angle than most people.”

Mr. Wymore also said he isn’t worried about facing bigotry as the city’s first transgender councilman.

“I don’t expect a lot of discrimination,” Mr. Wymore said. “But if it’s there, I’m happy to face it head on.”

hwalker@observer.com