Sharing Their Passion
Stephanie H. Winegrad and Hillary J. Moonay of Obermayer Rebmann Maxwell & Hippel LLP maintain thriving family law practices while mentoring the next generation of attorneys.
The most successful leaders reach their position through intelligence, a relentless work ethic, and a hunger to always improve. What’s more, when they reach the proverbial top of the mountain, they never forget the mentors who helped mold them, and they in turn seek to play the same role for the next generation.
For Stephanie H. Winegrad and Hillary J. Moonay, partners at the esteemed firm of Obermayer Rebmann Maxwell & Hippel LLP who specialize in all aspects of family law, it would be easy to focus on their own bustling practices and robust family lives. Yet, as successful leaders, they find fulfillment in passing on their knowledge to those coming up through the ranks.
In fact, Moonay recently received a 2026 Special Achievement Award from the Pennsylvania Bar Association (PBA) for starting the organization’s Leadership Development Program, which is part of the Family Law Section. The program admits a small group of young lawyers per year and assists them in getting involved with the PBA, extending their professional network, and building confidence as family lawyers and leaders. Winegrad has been a trusted co-chair of the program since its inception three years ago.
“The program I created that led to the award is probably the thing I am most proud of professionally,” Moonay says. “My absolute favorite thing to do is to teach and mentor young attorneys, especially younger female attorneys. Leading up to my year as chair of the Family Law Section, I was thinking about how being involved in the bar association has been so beneficial to me, both professionally and personally. The leadership of the PBA has played such a big part in that. This program combines my passion for teaching and mentoring younger attorneys while also helping our section develop our next generation of leaders.”
Winegrad’s volunteer work also includes serving as the vice president of the Pennsylvania chapter of the American Academy of Matrimonial Lawyers. “I really enjoy mentoring,” she says. “I like interacting with and helping young lawyers succeed, and it’s nice to give back to the community.”
Moonay and Winegrad share other similarities. Most recently, both were named to the 2026 Pennsylvania Top Five Family Law Super Lawyers list, a testament to decades of dedication, leadership, and excellence in family law. They are close in age, raised their children at the same time, and come from families of attorneys. What began as a professional relationship has grown into a close friendship, with the two speaking daily about both work and life.
Winegrad discovered family law while clerking for a family court judge and has spent more than 25 years in the field. She appreciates the many different hats she has to wear throughout the process.
“In the beginning, depending on the client, I’m more of a therapist and then I’m able to provide the legal advice,” she says. “There’s a lot of balancing throughout a case. It might be an easy case to resolve based on the law, but it’s the emotions that are driving the parties. You’re dealing with different types of people and different personalities, and that’s what I like.”
Winegrad believes in being responsive to clients, with a policy to always return calls or emails within the same day. She works with clients of all types but is especially adept at representing high-net-worth individuals. Recently she has seen an increase in “gray divorces” for people who have been married for 20 years or longer and have already raised their kids.
In those complex financial cases, she often works with professionals from other areas, like business or real estate. The deep bench at Obermayer has been invaluable.
“Very few large firms even have family law departments,” Winegrad says. “But, we serve our clients better at a full-service firm. If I need someone to look over a deed, lease, listing agreement of sale, or even an employment agreement, we have those lawyers on our team. When I have clients with businesses and I need certain documents reviewed, or estate plans, we have that capability.”
Moonay did not know right away that family law was her calling. After practicing briefly as a general litigator, she realized that her psychology degree and desire to help people on a personal level made her a natural. While she is known for being upfront and honest with clients, she also understands the challenges they are facing.
“Divorce is rarely an easy process, and even if your client is the person who wants to get divorced or needs to get divorced, there are still emotions,” she says. “My job is to give them the legal advice, but because it is such a personal matter, I feel like it’s so important for them to be comfortable with me as their attorney. I tell clients all the time, ‘You have to make sure this is the right fit for you.’”
Moonay treats every situation with the same determination to do what’s right for her clients, whether it’s an amicable divorce or a notable case that could have a lasting impact. That includes a landmark case, Caldwell v. Jaurigue, that went all the way to the Pennsylvania Supreme Court, in which she successfully helped to clarify child support responsibilities of third parties who have custodial rights to a child.
“Every case is about advocating for my client, and that’s what I find most rewarding,” she says. “Clients often come to me during times of uncertainty, and I love helping them get to the other side. When they’re coming to me, they’re usually dealing with uncertainty, and I have the opportunity to help them find clarity and a path forward.
“Family law is always different and you can always make an impact somehow, whether it’s just for one client and the facts of their case, or when it is creating new law [like Caldwell v. Jaurigue],” she continues. “From my perspective, every case is about advocating for that individual client. If the outcome ends up setting a precedent for others as well, that’s great.”
Both attorneys credit Obermayer for supporting their professional growth and encouraging their commitment to mentoring young lawyers. They say the firm’s support has enabled them to make an impact both within their clients’ lives and within the broader legal community. As a result, both have noticed more women pursuing family law since the start of their careers, a trend they view as a positive step in the right direction.
Obermayer Rebmann Maxwell & Hippel LLP
Doylestown Commerce Center
2003 S. Easton Road, Suite 108
Doylestown, PA 18901
(215) 606-0760
1001 Conshohocken State Road, Suite 1-210
West Conshohocken, PA 19428
(610) 825-3634
Photo by Alison Dunlap
Published (and copyrighted) in Suburban Life, August 2026.
