There are not many people who can say they have filled nearly every role in a courtroom. Philip A. Holloway is one of them.
From prosecutor to police officer to criminal defense attorney to substitute judge, Holloway has spent close to 27 years in the Metro Atlanta legal scene. He has testified as a witness, worked court security as a deputy sheriff, and now serves as a national legal analyst appearing on major networks across the country. The only role he has not held? Court reporter. And maybe bailiff (though he joked about that one during our conversation).
Holloway recently joined Daniel Matalon of A 2nd Chance Bail Bonds and host Tug Cowart on Justice Unfiltered to talk about his career evolution, his work on MK True Crime with the Megan Kelly Network, and what happens when relationships built over decades come together on some of the biggest cases in Georgia history.
A Career Built on Every Angle of the Justice System
Holloway does not just analyze the law from one perspective. He has lived it from nearly every seat in the courtroom.
That experience, he says, is what allows him to break down complex legal issues for audiences who are not lawyers. Whether he is discussing Fourth Amendment search and seizure rules or explaining the difference between a bailiff and a court deputy (yes, there is a difference), he knows how to translate legalese into something people can actually understand.
“I like to think that gives me the ability to think about things from different perspectives,” Holloway said. “And to the extent that might be something that helps my audience understand the justice system a little bit better, I try to bring those experiences to bear on the discussion.”
His military service in the Navy also shaped how he approaches his work. Both Holloway and Tug Cowart served, and that shared experience came up naturally during the conversation.
MK True Crime and the Megan Kelly Network
Holloway is now a host on MK True Crime, part of the MK Media company launched by Megan Kelly in 2024. The show, which also features attorney Ashley Merchant as a co-host, covers major cases with a legal lens that sets it apart from typical true crime content.
And big changes are coming. Holloway teased a format shift and some exciting announcements in the near future, though he kept the details close to the vest.
The partnership with Merchant is notable on its own. Merchant, a Metro Atlanta attorney, made national headlines when she exposed the relationship between Fulton County District Attorney Fani Willis and special prosecutor Nathan Wade. Holloway called her the “Erin Brockovich” of the whole situation, and her work on that case has had a lasting impact on both the legal world and the direction of the country.
When Megan Kelly brought her live tour to the Atlanta area in late 2025, Holloway and Merchant took the stage at Gas South Arena to introduce the show. Holloway laughed recalling the crowd’s reaction.
“When I walked out, I got a lot of, you know, applause. Politeness. When Ashley walked out, she got the rock star treatment.”
When A 2nd Chance Bail Bonds Met the Biggest Case in Georgia History
One of the most fascinating parts of the conversation was hearing Daniel Matalon’s firsthand account of processing bonds for some of the most high-profile defendants in recent memory.
A 2nd Chance Bail Bonds handled the bonds for Rudy Giuliani, Mark Meadows, Michael Roman (who was Ashley Merchant’s client), and David Schaefer. Matalon walked Giuliani in himself.
And the scene outside the office? Helicopters. Drones. Media everywhere.
“There were helicopters, drones. Yeah, whatever. It was good. It was fun,” Matalon said, keeping it characteristically low-key.
The whole process worked as smoothly as it did because of relationships that had been built over nearly two decades. Holloway and A 2nd Chance have worked together for years, referring clients back and forth and building the kind of trust that only comes with time.
“This deal on my side, at least, was a combination of relationships with people who have known each other for a long time and we trust each other,” Matalon explained. “And that is how you get stuff like that done at that level.”
Why Is America So Obsessed with True Crime?
The conversation also touched on a question that true crime fans have probably asked themselves: why are we so drawn to this stuff?
Holloway pointed to the O.J. Simpson trial as the first major moment that captured the country’s attention. But back then, there was no social media. No way for millions of people to have a global conversation in real time.
Now, platforms like YouTube and TikTok have turned trial watching into a participatory sport. People spend hours each day consuming true crime content, and many of them pick up enough knowledge to follow along with complex legal arguments.
“Social media has really driven this and it takes on a life of its own,” Holloway said. “And I think that is a good thing because on balance, there are some bad things I think. You know, if you want to make sure that courts, for lack of a better word, stay honest, then open it up so that the public can see almost everything that goes on.”
That transparency, he argued, is essential for accountability. Even if it means everyone suddenly thinks they are a legal expert.
Media Training: A Must for Lawyers
For attorneys who find themselves in front of cameras (whether by choice or circumstance), Holloway had some practical advice: get media training.
He went through formal training himself back around 2014 and 2015 when he started doing more work with CNN. The logistics matter (yes, learning how to powder your face in an emergency is a real thing), but understanding how journalists operate is even more important.
“If you do not know to get an agreement that what you are saying is off the record before you talk about it, then it is on the record,” Holloway said. “There are little things like that that people really need to know about.”
His other tip? Never ad-lib on live TV or radio. Have your message ready. Rehearse it. And know that even if you do not answer a reporter’s question directly, they will still use your 10-second comment on the evening news. That is an opportunity, not a problem.
The Relationship Between Bail Bondsmen and Attorneys
One thing that surprised Tug Cowart during the conversation was learning about the legal restrictions on attorneys when it comes to bonding clients out.
In Georgia, lawyers are prohibited from bonding out someone they are going to represent. So when a family member calls in the middle of the night saying a loved one is in jail, the person they really need in that moment is a bail bondsman, not an attorney.
That is where companies like A 2nd Chance come in. They are on the front lines of the justice process, often before an attorney ever gets involved.
Holloway has been referring clients to A 2nd Chance for nearly 20 years. The relationship, like so many others discussed in this episode, is built on trust, responsiveness, and a shared commitment to helping people through some of the hardest moments of their lives.
Listen to the Full Episode
Hear the complete conversation on the Justice Unfiltered podcast, available wherever you get your podcasts or watch on YouTube.
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About Justice Unfiltered
Justice Unfiltered is presented by A 2nd Chance Bail Bonds on Extra 106.3, Atlanta’s only conservative news and talk station. The podcast features candid conversations with law enforcement leaders, attorneys, elected officials, and community voices. Topics include bail reform, court processes, public safety, and the justice system.
A 2nd Chance Monitoring provides electronic monitoring and alcohol monitoring services across Georgia and Alabama, helping defendants stay compliant while awaiting trial.
