These Two Undercover Agents Outsmarted the World’s Greatest Con Man

J.J. Wedick and Jack Brennan © Jack Brennan

1977, the Thunderbird Motel. J.J. Wedick and Jack Brennan—two fresh-faced, maverick FBI agents—were about to embark on one of their agency’s first wire-wearing undercover missions. Their target? Charismatic, globetrotting con man Phil Kitzer, whom some called the world’s greatest swindler. Phil Kitzer was at the center of dozens of scams in which he swindled millions of dollars, but the FBI was mired in a post-Watergate malaise and slow to pivot toward a new type of financial crime that is now all too familiar.

We were thrilled to be able to chat with the author of the Chasing Phil, David Howard, as well as J.J. and Jack. Read on to learn more about the book, the adventures of Jack and J.J., and the future movie plans for this truly white-collar undercover sting.

SIGNATURE: How long did it take to write this book? To research it?

DAVID HOWARD: This project spanned just over three years from the first conversation I had about it until publication. I did a bunch of research over a span of about six months before I started writing, but I was interviewing Jack and Jim and gathering new details and bits of information right up until I sent the finished manuscript to Crown.

SIG: How did you develop an interest in this story?

DAVID: My first book, about a stolen artifact, included an FBI sting, which put me in touch with some people connected to the bureau. One of them connected me to Myron Fuller, whose undercover work had helped start the Abscam investigation in the late 1970s. Myron and I met in New York in 2014 and talked about a bunch of things, and at one point he said, “You know, it all started with two young agents out in Indiana who spent a year traveling with a con man.”

I stopped him and said, “Wait. Say that again.” As soon as those words came out of his mouth, I knew that that was my book. Then I started talking to the guys. I spent hours on the phone with Jim in particular that first month or two, and his ability to tell a story sealed the deal for me.

SIG: What did you learn by covering this story?

DAVID: A ton about the way undercover operations are run. I learned about the strengths and limitations of a giant organization like the FBI. And I was stunned and alarmed to realize how prevalent financial fraud and white-collar crime is—how relatively easy it can be to pull off when you have a bunch of deep inside knowledge of financial systems and instruments. The world is different now than when Phil Kitzer was running wild, but I change my passwords often.

SIG: What is most important for any author to remember when writing nonfiction that is not about their own life?

DAVID: With narrative nonfiction, it’s all about bringing characters to life, creating vivid scenes where there’s some action, and finding the story’s narrative arc so you can develop tension. Know what’s at the center of your story, too. I had a lot to work with: financial fraud, and deceit, and a key inflection point in FBI history. But I realized that early on that this was really about the connection that grew between these three guys. Once I grasped that it was a true-crime story that, ultimately, is a story about friendship, I saw clearly how to tell it.

We also got the chance to talk with former agents Jack Brennan and J.J. (Jim) Weddick, who, while undercover, helped to put an end to globetrotting con-man Phil Kitzer’s schemes.

SIG: In the book, David writes that Phil was corrupt, but also capable of doing good. Do you believe this to be true of all people who do bad things?

J.J. WEDICK: Everybody makes mistakes, but most folks can be rehabilitated, I think. True evil does exist, like with guy who just shot up Las Vegas, but that’s a tiny minority. That’s why I thought there was a possibility for Phil in life after the arrest.

DAVID: Agreed. One of my core beliefs in writing stories about people is that no one is all good or all bad. Finding the layers of complexity in people is what makes stories interesting, and what makes them stay with you.

SIG: What are your feelings on “Robin Hood” figures?

DAVID: That story is several centuries old, so there’s obviously something about it that resonates with people in a powerful way. I just think you have to carefully examine each person who adopts that mantle—examine his motivations, the way he’s going about his business. Phil Kitzer was not a Robin Hood, much as he liked to think of himself that way. Someone may have incidentally benefited from one of his schemes, but he was primarily out there for himself.

J.J.: I think there’s something real there, too. But once you get your money into your greedy little hands, we all get to see how much you’re going to pass on to the poor. It doesn’t always play out that way.

SIG: With the rights for this story sold to Warner Bros., what are your thoughts on the possibility of a movie being made? Do you think Robert Downey Jr. would make a great Phil?

J.J.: Yes, because there are some qualities I think Downey sees in Phil that he might have experienced along the way himself, and he thinks he can play that part like nobody else. Phil was on top of the world, then he crashed and made his way back up. Likewise, Downey experienced some difficulty and remade himself to the extent that, look at him today.

DAVID: These guys knew Phil, so they’re the ultimate authorities on this question, but I’ll say this: I read hundreds of pages of Kitzer’s testimony, which included lots of stories. I read transcripts of times he was secretly recorded before the arrest, and got a sense of the rhythm of his speech, how convincing he could be. Based on all of that, I can’t think of a more perfect choice than Downey.

SIG: What was the most unexpected thing that came out of working undercover on this case?

JACK BRENNAN: I was surprised how the FBI went from reluctance and opposition to this case to acceptance and even support for the idea of white-collar crime being a significant organized-crime problem.

J.J.: For me, it was Kitzer agreeing to cooperate after the arrest. Who would’ve thought that in four month’s time, rather than go with his cronies, that he would make his bed with us? Also, the extent to which the FBI embraced undercover work, in contrast to what they did previously. J. Edgar Hoover had always been worried about undercover agents joining the dark side.

SIG: How much more difficult did your job become when you developed a friendship with Phil?

J.J: Well, the mission was always paramount. The emotional component was secondary—but I also had moments of clarity where I thought that it was conceivable that if Phillip decided to cooperate, that there could a life for him after.

JACK: Phil was considerate of both of us and at times even tender. Phil mostly treated the people he met along the way nicely. We periodically had to remind each other not to open ourselves up too much to him because it would complicate things later.

Phil Kizer in the 1960s © Minneapolis Star Tribune/Chasing Phil

Phil Kizer in the 1960s © Minneapolis Star Tribune/Chasing Phil

SIG: In order to conduct the mission successfully, you had to be in character, and put on a show. When you finally were able to reveal your true selves to Phil, how did that feel?

J.J: My heart was pounding, and my stomach was churning. The book does a good job of describing that. I started talking, which is what I do, especially when I’m cranked up. I just wanted to convey to him: Listen to me. This doesn’t have to end here.

JACK: It was difficult. When his arrest became public, Phil’s life would be in danger. Jim and I felt on a personal level bad about this, though it was necessary outcome of the undercover operation.

SIG: Do you believe the lies we tell ourselves can eventually become truth? Did you ever have moments when you had to remind yourself that you’re undercover?

J.J.: I know that have been some cases where that’s happened, which is why today they do psychological tests, but I never lost myself. Phil was too much about today, this moment. I saw no future in behaving like he did. If anything, I needed to get off the train once in a while and get back to a normal life.

JACK: We tried to stay close to who we really were throughout the undercover operation. We did have to be more flamboyant, more freewheeling and spontaneous then we normally were, and more willing to follow what Phil wanted to do than we normally would be. Jim and I were fortunate to be partnered in this. We were able to stay in balance with who we really were and not go overboard trying to be like the people we were meeting. There were times we would remind each other to be careful about what we did or said.

SIG: You both paved the way for undercover agents. How do you think being an undercover agent has changed from the 70s to now?

J.J.: First of all, I can’t believe the things I did then versus now. Today, without any training, they wouldn’t even let us go to that first meeting we had with Phil. And safety was out the window; it was all about the mission. We spent weeks trying to convince the bureau we should go with Phil to Haiti. Would I do that today? No. We felt we could talk our way out of or into anything. And I was using my own name, my apartment.

SIG: “Maybe everyone was part con man. Maybe everybody was in the game, and Phil just knew better than anyone else how to play.” How has working closely with one of the world’s most charming con men changed your view on conning? Have you viewed others differently? Yourself?

JACK: This increased my awareness of the potential to be the victim of a con or a crime. It took a personal decision not to view everyone with suspicion in order to not be paranoid about all my dealings in life.

J.J.: I’m a little more cynical, too, a little more knowledgeable about how criminal organizations can wreak havoc on our justice system and economy. These guys we spent time with—they were only influenced by the next deal, the next roll of money, the next plane departure. They don’t operate on the same schedule, or by the same norms, than the rest of us.

SIG: How did you feel when the mission came to an end?

J.J.: We were all relieved about the end of the undercover part. We were happy. At the same time, we had a lot left to do in terms of the prosecution. If it’s done right, it’s going to take another three to four years to complete it. When we arrested Kitzer, I was like, “That doesn’t mean anything.”

JACK: I was transferred down to Mobile, Alabama, but we had only reached the beginning of a very intense phase of the investigation. Because of the trials, one year following Phil’s arrest I was in Mobile less than 140 days due to travel related to prosecuting the Kitzer cases.

SIG: When you look back on your adventures undercover, have the memories faded at all? If you could relive one moment of that time, which would it be?

J.J.: There was a moment when I was in my apartment, planning a trip to Miami and then Hawaii. My roommate looks at me and says, “Where do I get a job like that?” We’d been authorized to travel anywhere in the U.S., and we had some freedom and authority to conduct an investigation to pursue Phil in a way that hadn’t been done before.

JACK: What I remember most is the feeling of team, the great partnership with Jim and the prosecutors—the support and change of direction that occurred with the FBI. And the restoration of my marriage. I’m truly grateful for Becky’s forbearance and love and I’m thankful for the many blessings that have resulted from our reconciliation.

SIG: What was it like to see a significant piece of your life turned into a book?

J.J.: Having all of those conversations with Dave gave us ability to go back in a time capsule, and relive it in a way that was more fun, because it didn’t come with the emotional trauma and danger, the stress.

JACK: I find it interesting to see how things look from a third-party perspective about what we did. It’s pretty amazing to look back and see how two guys who wouldn’t take no for an answer caused the FBI to change directions in such a significant way.