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Former Wheatfield town attorney becomes a woman

WHEATFIELD – “I think I feel more at ease than I ever did,” Roberta Jean O’Toole said the other day.

After 63 years of being Robert James O’Toole, and town attorney in Wheatfield for 24 of the last 26 years, O’Toole has become a woman, something she said she wanted to do since she was a boy in Niagara Falls.

Transgender women aren’t new, and with former Olympic decathlon champion Bruce Jenner becoming Caitlyn Jenner, they’ve been Page One news lately.

But for decades, politics, economics and plain old hesitation kept O’Toole in a man’s role. O’Toole is apparently the first public official in Western New York to go the transgender route.

At the end of June, O’Toole retired from her town job, which included serving as Wheatfield’s human resources director. At the time, she said the reason was an offer to form a new law practice in Buffalo.

That was, as they say in court, the truth, but not the whole truth.

O’Toole had decided, in her words, “Enough is enough.” Enough faking. Enough concealing the truth about what she feels she was meant to be.

It gave her a chance to stop living a dual life. She would no longer have to wear loose-fitting suits to conceal her breasts, obtained through hormone therapy. She could dress as a woman whenever she pleased, not just while on vacations and at out-of-town job interviews.

O’Toole legally changed her name as of a Friday filing in the Niagara County Clerk’s Office. She said she has undergone “some gender-conforming surgery or procedures.”

She has joined forces with attorney Heidi I. Jones for a new law firm in Buffalo’s Allentown neighborhood. For them, O’Toole said, “there couldn’t be a better area in all of Western New York.”

Jones & O’Toole will focus on small business, tax, real estate and nonprofit law.

For Jones, 43, O’Toole, who earned her law degree at Harvard University, is a godsend as a law partner.

“She’s got amazing experience, Harvard Law, how could you do better? We have a good personality fit,” said Jones, a Pennsylvania native who graduated from the University at Buffalo Law School. She entered a same-sex marriage less than a month ago.

She and O’Toole met about four years ago at a event sponsored by Buffalo Queer Women, a group Jones founded. “She showed up at some events and we hit it off,” Jones said.

Gender identity disorder

Although born a biological male, O’Toole said she always wanted to be female. When she was 17 or 18 years old, “My mother caught me with some female clothing,” O’Toole said. Her mother sent young Robert to a psychiatrist, where O’Toole denied everything and only attended one session.

Dr. Thomas Mazur, the Buffalo psychologist who has been counseling O’Toole for the past 14 years, diagnosed her with “gender dysphoria,” or what was formerly called “gender identity disorder.”

“They want to be seen in the world as the gender that they internally experience,” Mazur said. “And you try to assess that they’re not running away from being gay, that they’re not cross-dressers and that there’s no other problems that might interfere with that diagnosis, such as schizophrenia.”

Mazur, who signed an affidavit to support O’Toole’s name change application and to allow her to change her gender designation on her driver’s license, said the “acid test” for a prospective transgender person is to live the life of the sex they want to become, 24 hours a day, without therapeutic hormones “crossing the blood-brain boundary.” Some, he said, can’t hack it.

Thus, going to events like those of Buffalo Queer Women in female garb could be viewed as practice.

“I think it was an opportunity for me to sort of be myself,” she said. “There are a number of places where I was able and willing and wanted to go in female mode, but there were a number of places, especially in Niagara County, where I couldn’t go because I was and am fairly well-known.”

O’Toole was married for 24 years until her divorce in 2001, and fathered two sons and two daughters. She said gender identity issues were not the reason for the divorce, and although she hasn’t discussed the transition with her ex-wife, O’Toole is sure she knows, at least through their adult children.

“They’ve certainly seen what I wear around the house,” said O’Toole, who still lives in the hamlet of Bergholz with one of her sons. “None of them have stopped talking to me.”

Why, if O’Toole wanted to be female for most of her life, did she wait until age 63?

“I think it’s not unusual for people to repress it,” O’Toole said. “I just wasn’t willing to take the leap then, to take the risk. I wasn’t willing to give up what I had at that point in time. I think most of it was economic. I really didn’t have the confidence that I would be able, particularly as a trans woman, to generate the kind of business that I would have needed to generate to make up for the loss of town income.”

She said in that regard, reaching 20 years in the state retirement system and being fully vested for a pension was “one of the most liberating experiences of my life.” She stayed with the town for almost five more years at a salary of more than $90,000 a year, accumulating more pension credits.

“Nobody knew it, but I was also looking around at other positions,” she said. She applied for human resources and legal positions in the Rochester area, going to job interviews as a female, but she wasn’t hired. “I think age had more to do with it than the fact that I was trans,” she said. “People my age were not likely to get hired for anything.”

Time is now

O’Toole said she decided to come out now because she’s representing James Szwedo, a Republican candidate for mayor of Niagara Falls, in a dispute with the city over back taxes. O’Toole said the issue could lead to a lot of local publicity that might have resulted in the inadvertent revelation of her gender change. After a Buffalo News reporter noticed her legal filing to change her name, she decided to go public.

“So far it’s been pretty good. The acceptance level has been far better than I had anticipated. I anticipated some negativity, and I really haven’t had very much of that, if any,” O’Toole said.

She admitted there was an element of fear, too, but at a women’s seminar in Long Beach Island, N.J., a few years ago, she heard a speaker whose message resonated with her.

“You have to be willing to move on and let go of the past, because you can’t grow if you don’t,” O’Toole said.

Before joining the Town of Wheatfield, O’Toole worked at a major Buffalo law firm that is now defunct.

“I am not the first trans lawyer in Buffalo history,” O’Toole said. “One of the partners did transition and was terminated. That would have been about 1980. Another thing that happened in that firm was, one of the partners came out as gay. … There was also a female-to-male student at UB who did some clerking downtown.”

‘Nothing earth-shattering’

O’Toole is using a slightly higher voice than she did as town attorney, which she said no longer requires a conscious effort but is not the result of any medical treatment.

O’Toole always wore her hair longer than most men. “That was so when I chose to I could fix my hair and go out as a female,” she said. It was gray when she was a man, but now it’s tinted light blonde and curled. For The News interview, O’Toole also wore pink nail polish, a skirted suit, low-heeled shoes and pierced hoop earrings.

“Toward the end it was sort of uncomfortable trying to pull off being a male,” O’Toole said. “I think that I was kind of odd-appearing.”

Wheatfield Supervisor Robert B. Cliffe said O’Toole stopped by Town Hall on Wednesday in female garb. Cliffe said he wasn’t there at the time, but he heard about it.

Asked if he was surprised, Cliffe said, “A little, but nothing earth-shattering.”

O’Toole said she didn’t think she could have remained town attorney after the gender transition. She said, “I would not have wanted to put the board members in that position and I would not have wanted to put myself in the position of being a campaign issue, because I think that would have happened.”

Cliffe said, “I’m sure it would have been a little hard on him from some persons’ perspective. I don’t know that the board would have had any comment either way.”

O’Toole said she was sure board members heard rumors about her plans over the years. Cliffe declined to comment about that, but the supervisor said, “It’s his life. He’s allowed to do with his life as he sees fit.”

The supervisor added, “Bob did a lot of good for the town. He was around for 23 or 24 years as town attorney, started doing work for the town in 1989, became full time seven or eight years ago. He’s been involved in virtually everything that’s happened in the town in the past 25 years and he has chosen to retire and go on with his life. I hope he has a good one.”

O’Toole said, “I’m looking forward to this new opportunity and this new chapter in my life. It’s really exciting.”