Kimberly Guilfoyle Faces Explosive New Claims From Former Fox News Colleague Days After Resigning as Ambassador to Greece
Kimberly Guilfoyle Faces Explosive New Claims From Former Fox News Colleague Days After Resigning as Ambassador to Greece
Kimberly Guilfoyle’s departure from her diplomatic position in Greece has been followed by another wave of controversy, this time involving claims from someone who once worked alongside her at Fox News.
Lisa “Kennedy” Montgomery, a former MTV personality and longtime Fox News contributor, has publicly described what she says were unusual and inappropriate interactions with Guilfoyle during their years at the network.
Among her most striking allegations is that Guilfoyle showed colleagues intimate photographs of a man she was dating alongside images of his American Express credit card.
The account appeared in a Daily Mail commentary published on October 15, 2026.
It arrived just two days after Guilfoyle resigned as United States ambassador to Greece following reports of alleged financial misconduct.
The timing immediately attracted attention.
Guilfoyle was already facing questions over claims that she had sought $100,000 from a political donor to pay an American Express bill while offering assistance with access to officials in the Trump administration.
She has denied wrongdoing and disputed the authenticity of the messages central to that controversy.
Montgomery’s newly published recollections concern a different period in Guilfoyle’s life, before her diplomatic appointment.
They have not been independently established as fact.
But they have added another layer of public scrutiny to the former television personality’s already turbulent departure from government service.
What Lisa Kennedy Montgomery Claims Happened at Fox News
Montgomery, widely known by her television name Kennedy, worked in the same media environment as Guilfoyle after joining Fox in 2012.
In her Daily Mail commentary, she described initially having a friendly relationship with the former prosecutor and television host.
She said that the two women found common ground through conversations about California politics and Guilfoyle’s former husband, Gavin Newsom.
However, Montgomery claimed she gradually became uncomfortable with some of Guilfoyle’s behavior.
Her allegations centered partly on conversations about romantic relationships and sexually explicit photographs she said were shown to colleagues.
Montgomery described one man Guilfoyle was allegedly dating and claimed that the photographs included his credit card information alongside intimate images.
According to Montgomery, there were multiple examples of these pairings.
The account was presented as her personal recollection of events at Fox News.
It has not been established through a court finding or publicly presented independent evidence.
The Unusual American Express Detail
The most widely discussed portion of Montgomery’s account involved American Express cards.
She alleged that Guilfoyle showed her and other people images of a man’s American Express Black Card.
The photographs reportedly included both sides of the card.
Montgomery claimed that these images were accompanied by intimate photographs of the person to whom the card belonged.
She also suggested that this was not an isolated example.
The allegations are significant because they concern the possible sharing of intimate images and private financial information in a workplace setting.
However, no independent verification of the specific photographs described by Montgomery has been established in the available reporting.
Her account should therefore be understood as an allegation rather than a confirmed record of Guilfoyle’s conduct.
Kennedy Also Described Conversations About Relationships
Montgomery’s commentary included additional claims about Guilfoyle’s behavior while they worked at Fox.
She alleged that Guilfoyle frequently discussed her romantic and sexual relationships.
According to Montgomery, some of those conversations involved claims that other people at the network were romantically interested in Guilfoyle.
Montgomery characterized the behavior as unusually open and sometimes uncomfortable.
Her account presented a personal interpretation of Guilfoyle’s workplace personality.
As with the photographs, those descriptions have not been independently proven.
The claims have nevertheless attracted attention because they emerged during a week in which Guilfoyle’s professional conduct was already facing scrutiny.
Why the Timing Has Attracted So Much Attention
Montgomery’s article appeared shortly after Guilfoyle’s diplomatic career came to an abrupt end.
On October 13, 2026, the White House confirmed that Guilfoyle had been asked to resign as ambassador to Greece.
Guilfoyle subsequently announced that she was stepping down.
Her departure followed reports about alleged financial arrangements and other concerns involving her behavior before and during her diplomatic posting.
The allegations were serious enough to prompt scrutiny from lawmakers and questions about potential ethics investigations.
Montgomery’s commentary added allegations from a separate chapter of Guilfoyle’s professional life.
Although the incidents described were not directly connected, their publication within days of one another intensified public attention surrounding the former ambassador.
The $100,000 American Express Controversy
The dispute involving political donor Eric Deters became one of the central issues preceding Guilfoyle’s resignation.
Deters, a Kentucky businessman and Republican donor, alleged that Guilfoyle asked him to pay $100,000 toward her American Express credit card bill.
According to reporting by The Wall Street Journal and CBS News, the alleged request occurred in July 2025, shortly before Guilfoyle’s Senate confirmation hearing.
Deters claimed that the request was connected to assistance he wanted with access to officials in the Trump administration.
He described the proposed arrangement as an exchange of financial support for influence.
Guilfoyle’s representatives have disputed the allegations and challenged the authenticity of the messages reported by news organizations.
The dispute remains contested.
Text Messages Became Central to the Dispute
Deters provided news organizations with messages he alleged were exchanged with Guilfoyle.
The communications reportedly concerned paying an American Express balance and the financial arrangements surrounding the payment.
Some of the reported messages suggested that a direct transfer to American Express would not appear in certain financial records in the way an ordinary payment might.
Deters said he understood the request to involve assistance with his legal and tax-related concerns.
He also said he did not ultimately provide the requested $100,000.
Guilfoyle’s legal representatives have challenged his characterization of the communications.
They have also argued that he owed her money connected to previous work.
No final judicial determination has established the competing claims.
Guilfoyle’s Lawyers Offered a Different Explanation
Guilfoyle’s legal team has denied that she engaged in improper conduct.
Her lawyers stated that Deters owed her approximately $150,000 for speaking engagements and consulting work performed before her ambassadorial nomination.
They disputed the suggestion that she had improperly offered government access in exchange for a personal payment.
They also challenged the authenticity of messages attributed to her.
These competing explanations are central to understanding the controversy.
Deters portrays the alleged request as an improper financial solicitation tied to political influence.
Guilfoyle’s representatives deny that interpretation and maintain that she has been wrongly accused.
Both positions need to be distinguished from facts established through an independent legal process.
Eric Deters Filed a Defamation Lawsuit
On October 15, 2026, Deters filed a lawsuit against Guilfoyle and members of her legal team in Kentucky state court.
The lawsuit followed public statements disputing his allegations.
Deters contended that statements made by Guilfoyle’s representatives harmed his reputation.
Local reporting also described claims involving invasion of privacy and breach of contract.
The filing introduced a new legal dimension to a dispute that had already received substantial national attention.
However, filing a lawsuit does not establish that the allegations are true.
It begins a legal process in which claims can be contested, evidence examined, and legal arguments presented.
The outcome remains uncertain.
The White House Asked Guilfoyle to Step Down
Guilfoyle’s resignation was not simply a routine diplomatic transition.
White House officials confirmed that the administration had asked her to leave the position.
The decision came after reports raised questions about her conduct and financial relationships.
President Donald Trump had publicly expressed dissatisfaction with the developing controversy shortly before the resignation.
On October 13, the White House announced that Guilfoyle had been asked to resign.
She subsequently issued a statement acknowledging her departure.
The move ended a diplomatic posting that had begun less than a year earlier.
It also raised questions about the administration’s process for evaluating and responding to allegations involving high-profile appointees.
Guilfoyle Denied the Accusations
After announcing her resignation, Guilfoyle strongly rejected allegations of improper conduct.
She maintained that the accusations were false and indicated that she intended to defend her name and reputation.
She also expressed appreciation for the opportunity to serve as ambassador to Greece.
Her response emphasized her continued commitment to public service and her political associations.
It is important to distinguish that denial from Montgomery’s newly published account.
The statement clearly addressed the misconduct allegations surrounding Guilfoyle’s diplomatic role.
Available reporting does not establish that she separately issued a detailed response to each of Montgomery’s specific claims about photographs shown during the Fox News years.
The State Department Faced Questions About Possible Investigations
Reporting surrounding Guilfoyle’s departure also raised questions about scrutiny by the State Department’s Office of Inspector General.
News organizations reported that the watchdog was examining allegations connected to her conduct.
The concerns extended beyond the American Express dispute.
They included reports involving gifts, private travel, business relationships, and interactions with officials during her time in Greece.
Lawmakers also called for greater examination of the accusations.
But an investigation is not the same as a finding of wrongdoing.
Its purpose is to determine what evidence exists and whether rules or laws may have been violated.
Public reporting had not established a final outcome as of October 18, 2026.
Other Allegations Concerned Her Diplomatic Conduct
Separate reporting by The Wall Street Journal raised questions about Guilfoyle’s dealings with business figures while serving in Greece.
The reports described alleged relationships with Greek executives and involvement in activities that could create concerns about the use of diplomatic influence.
They also discussed allegations involving luxury travel and access to private diplomatic settings.
Guilfoyle denied wrongdoing.
These accounts contributed to the scrutiny that preceded her resignation.
However, they are distinct from Montgomery’s allegations concerning her earlier workplace behavior.
Keeping those issues separate is important because they involve different periods, sources, and factual disputes.
Guilfoyle Had a High-Profile Career Before Diplomacy
Long before becoming ambassador to Greece, Guilfoyle was a recognizable television personality.
She previously worked as a prosecutor in California before developing a career in legal commentary and political broadcasting.
At Fox News, she became widely known as a co-host of The Five.
The program brought together commentators discussing political developments, public affairs, and current events.
Guilfoyle’s television appearances made her familiar to a national audience.
She later became involved in Republican political campaigns and developed close ties to Donald Trump’s political circle.
That background contributed to the attention surrounding her appointment to a prominent diplomatic position.
Her Departure From Fox News Had Previously Drawn Scrutiny
Guilfoyle left Fox News in 2018.
Her departure was followed by reporting about allegations of workplace misconduct.
HuffPost published claims that inappropriate behavior had contributed to her exit.
Later reporting also examined allegations involving sexually explicit material and interactions with colleagues.
Guilfoyle denied those accusations.
Her attorney at the time characterized them as baseless.
Montgomery’s October 2026 commentary revisited some of the themes associated with those earlier reports.
However, the publication of similar allegations by different sources does not by itself establish their truth.
Each claim requires examination on its own evidence.
Why Montgomery’s Account Has Renewed Interest in the Fox Years
The significance of Montgomery’s commentary lies partly in her professional connection to Guilfoyle.
She was not writing as a distant observer who knew the former television host only through public appearances.
She described experiences from a period when both women worked within the Fox media environment.
Her account therefore offered readers a purported firsthand perspective.
But personal recollections can still be incomplete, disputed, or difficult to corroborate.
The fact that someone describes witnessing an event does not eliminate the need for independent verification.
Montgomery’s allegations remain her account of what occurred.
The Sharing of Intimate Images Raises Broader Workplace Questions
If intimate photographs are shown to colleagues without appropriate consent, the situation may raise questions about professional boundaries and privacy.
Workplaces generally require employees to consider the impact of personal material shared with others.
Unwanted exposure to explicit images can create discomfort and may implicate workplace conduct policies.
There may also be privacy concerns involving the person depicted in the photographs.
However, whether any particular conduct violated a policy or law depends on facts that have not been fully established in Montgomery’s account.
The available reporting does not provide a complete verified record of the images or the circumstances in which they were allegedly shown.
Those limitations should remain clear.
The American Express Connection Drew Particular Attention
One of the unusual features of the controversy is that American Express appears in two separate sets of allegations.
Montgomery’s account describes alleged photographs of a man’s credit card during Guilfoyle’s Fox News years.
The donor dispute concerns a reported request for $100,000 toward an American Express balance in July 2025.
The similarity made Montgomery’s remarks particularly noticeable after the financial allegations became public.
But the two accounts should not be treated as proof of one another.
They involve different circumstances and different sources.
The appearance of the same credit card company in both stories does not establish a shared motive or a single pattern of wrongdoing.
Her Relationship With Donald Trump Jr. Added to Her Public Profile
Guilfoyle’s personal relationship with Donald Trump Jr. made her an especially recognizable figure within Trump’s political circle.
The pair were together for several years and became engaged.
They frequently appeared at political events and campaign gatherings.
The relationship ended in late 2024.
Guilfoyle subsequently received the nomination to serve as ambassador to Greece.
Her appointment attracted attention because of her longstanding relationship with the Trump family and her prominent role in Republican political messaging.
Her resignation has therefore been discussed in the context of both her diplomatic responsibilities and her history as a high-profile political ally.
She Also Has a Connection to California Governor Gavin Newsom
Before her relationship with Donald Trump Jr., Guilfoyle was married to Gavin Newsom.
The couple married in 2001.
At the time, both were building public careers in California.
Their marriage ended in divorce in 2006.
Newsom later became governor of California.
Their former marriage has remained a subject of media interest because both developed prominent political associations.
Montgomery referenced Newsom in her account of how she initially connected with Guilfoyle at Fox.
However, the former marriage is background information rather than evidence relevant to the more recent allegations.
The Resignation Raised Questions About Diplomatic Accountability
An ambassador represents the United States in another country.
The position involves maintaining relationships with foreign officials, communicating American policy, and supporting diplomatic priorities.
Because the role carries public authority, questions about potential conflicts of interest can become particularly serious.
Financial relationships with donors or private businesses may require scrutiny when they intersect with official duties.
That is why allegations involving payments, gifts, or privileged access attract attention beyond the personal reputation of the individual official.
In Guilfoyle’s case, the administration’s request for her resignation demonstrated that the controversy had become a significant personnel matter.
It did not, however, settle the underlying factual disputes.
What Has Been Confirmed So Far?
Several developments can be established from published reporting.
Guilfoyle was asked to resign as ambassador to Greece and announced her departure on October 13, 2026.
Eric Deters has publicly accused her of requesting $100,000 toward an American Express bill in connection with assistance he sought from the administration.
He subsequently filed a lawsuit in Kentucky.
Guilfoyle and her representatives have denied wrongdoing and challenged the allegations.
Lisa Kennedy Montgomery published an account alleging inappropriate sharing of intimate photographs during Guilfoyle’s time at Fox News.
That account has been widely reported.
But its specific allegations have not been independently established as fact.
What Remains Unresolved?
The truth of the disputed financial communications remains a central question.
Guilfoyle’s representatives contest the allegations made by Deters.
His lawsuit may lead to further examination of the statements and financial arrangements described in the dispute.
Questions also remain about the findings of any official investigation into her diplomatic conduct.
Separately, Montgomery’s claims concerning the Fox News years have not been resolved through publicly established evidence.
There is no basis for treating all the allegations as proven merely because they appeared close together in news coverage.
The distinction between an accusation, an investigation, and an established finding is essential.
Kimberly Guilfoyle’s Latest Controversy Brings Her Past and Present Under Scrutiny
Kimberly Guilfoyle’s resignation as ambassador to Greece on October 13, 2026, brought a high-profile diplomatic appointment to an abrupt end.
Her departure followed reports alleging improper financial requests and other conduct connected to her political and diplomatic relationships.
Guilfoyle has strongly denied wrongdoing.
Days later, former Fox News colleague Lisa Kennedy Montgomery published an account describing alleged behavior from Guilfoyle’s earlier television career.
Montgomery claimed that Guilfoyle showed colleagues intimate photographs of a man alongside images of his American Express card.
She also alleged that Guilfoyle frequently discussed her romantic and sexual relationships in the workplace.
Those claims remain allegations.
They have attracted attention partly because of the separate dispute involving Republican donor Eric Deters and a reported $100,000 American Express payment request.
Deters has filed a defamation lawsuit, while Guilfoyle’s representatives continue disputing his account.
At the center of the larger controversy are questions about professional conduct, financial relationships, political influence, and accountability in public office.
The confirmed facts establish that Guilfoyle has left her ambassadorial post and that legal and public disputes surrounding her conduct are continuing.
They do not establish that every allegation against her is true.
As the situation develops, further evidence and any findings from legal or official proceedings will be essential to determining what actually occurred.
For now, her unexpected departure from Greece and the renewed attention to her Fox News years have placed multiple chapters of her public career under intense scrutiny.