Maureen E McPhilmy became known to the public through her high-profile marriage and divorce. But there’s much more to her story than just these connections. Her journey from small-town beginnings to building her own life makes for an interesting tale worth telling.
Who Is Maureen E McPhilmy?
Maureen E McPhilmy was born on May 11, 1966, in Chittenango, New York. She grew up in a working-class family where her mother worked as a gardener and her father worked at a local market. Her early life wasn’t always easy.
McPhilmy’s parents divorced when she was only five years old. This early experience with family change would later echo in her own adult life. She went to St. Peter’s School for her education.
Before becoming a public relations executive, McPhilmy started her working life as a waitress. This humble beginning shows her work ethic and determination to build a career from the ground up. Many people can relate to starting with entry-level jobs.
Standing 5’9″ with blonde hair and brown eyes, McPhilmy is described as having a striking appearance. She is an American citizen who follows the Christian faith. These basic facts help paint a picture of who she is.
Career Achievements
McPhilmy built a successful career as a public relations executive. In this role, she helps manage how the public sees individuals and organizations. This career choice shows her skill with communication and people management.
Her work in public relations has given her a professional identity separate from her personal connections. Though details about specific clients aren’t widely known, her expertise in this field has been her main professional focus.
As a PR specialist, McPhilmy’s job involves strategic communication and helping clients develop their public image. This kind of work requires strong people skills, strategic thinking, and the ability to shape public opinion effectively.
Personal Relationships
McPhilmy met Bill O’Reilly in 1992 in New York. Their relationship led to marriage on November 2, 1996, in a ceremony held in Westbury, United Kingdom. The couple had two children together during their marriage.
Their daughter Madeline (sometimes spelled Madeleine) and son Spencer were born during this union. The family appeared from the outside to have the typical life of a successful American household with two children.
The marriage lasted approximately 14 years before the couple separated in 2010. Their divorce was finalized on September 1, 2011. What followed was a long and difficult legal battle between the former spouses.
After her divorce, McPhilmy found love again with Jeffrey Gross, a detective with the Nassau County Police Department. Gross was previously married to Kathleen McBride, who sadly passed away from cervical cancer in 2006.
Gross brought two teenage children from his previous marriage into their relationship. This created a blended family situation, bringing together children from both of their previous marriages into a new family unit.
Custody Battles and Legal Issues
The divorce between McPhilmy and O’Reilly turned into a lengthy custody dispute over their two children. In 2016, McPhilmy was granted full residential custody of both children, though O’Reilly maintained visiting rights and shared legal custody.
Both teenagers had expressed their preference to live with their mother. This decision by the court recognized the children’s wishes while still allowing their father to remain involved in their lives through legal custody and visitation.
The custody arrangement didn’t come without complications. In 2015, McPhilmy was found in civil contempt of court and fined $310,000 for violating the custody agreement when she refused to transition their daughter to O’Reilly’s home during his scheduled time.
McPhilmy had argued that their then-16-year-old daughter didn’t want to go and was old enough to make her own decisions. However, the court rejected this reasoning, insisting that the custody agreement needed to be followed regardless.
Legal Battles After Divorce
Five years after their divorce, in 2016, O’Reilly filed a $10 million lawsuit against McPhilmy. He claimed she had tricked him into signing their divorce settlement. When McPhilmy didn’t respond to the suit, it initially resulted in a $14.5 million award against her.
This award was later canceled following an appeal. The ongoing legal battles showed how complicated and bitter the aftermath of their marriage had become, even years after the official divorce had been completed.
O’Reilly later filed another lawsuit against Michael Klar, the attorney who had represented McPhilmy during their divorce. He claimed that Klar had helped McPhilmy trick him into entering an unfavorable separation agreement in 2010.
In a recent development from April 2025, O’Reilly’s $10 million fraud lawsuit against Klar has been unsuccessful. A New York judge blocked O’Reilly’s attempt to stop subpoenas served to his divorce lawyer and personal accountant as part of the ongoing legal proceedings.
Current Life and Residence
McPhilmy currently lives in Manhasset, New York with her husband Jeffrey Gross. During her separation period, reports show she purchased a new home about half a mile from the waterfront property she had shared with O’Reilly and their children.
She bought this home in May 2010 under her maiden name for $2.5 million. She changed her voter registration to the new address while O’Reilly kept his registration at their former shared home.
Final Thoughts About Maureen E McPhilmy
Maureen E McPhilmy’s life story shows how someone can rebuild after a difficult public divorce. While she keeps a more private life compared to her former husband, she has still had to deal with ongoing legal issues from their relationship.
Despite these challenges, McPhilmy has created a new family with her current husband while raising her children. Her career in public relations has given her a professional identity separate from her high-profile marriage and divorce.
Her story reminds us that there’s usually more to someone’s life than what makes headlines. Behind the public legal battles and famous connections is a woman who has worked to build a career and create a stable home for her family.
For many people going through difficult divorces or family changes, McPhilmy’s journey might offer some perspective. Moving forward after relationship challenges is possible, even when those challenges play out in the public eye.
This article about Maureen E McPhilmy was carefully researched to provide accurate information about her life journey, career, and personal relationships.