Inside the Mind of the Golden Boy Killer | Behind the Interview

Added: 2026-05-23

[00:00:00]It's Friday, so that means a new episode of the award-winning original series Interview with a Killer is airing this weekend. And we're going to watch together investigative journalist David Scott confront a Princeton graduate who fatally shot his father after his weekly $1,000 allowance was slashed to $300 a week. And the jury didn't buy his attempt of an insanity defense after details of the crime show that he placed the gun in his father's hand in an attempt to make it look like a suicide.

[00:00:30]an entitled golden boy, a paranoid arsonist, a violent murderer. That's the Tommy Gilbert Jr. we'd been learning about. I wanted to meet him for myself.

[00:00:42]So, we asked him for an interview and got back one sentence scribbled in handwriting that looked more like a child's than a Princeton graduates. It was our first clue that Tommy was unwell.

[00:00:54]Our second clue came shuffling into the prison interview room.

[00:00:59]>> How are you? Please join me here.

[00:01:03]I'm David Scott.

[00:01:05]The Tommy Gilbert I met there was a far cry from the so-called golden boy.

[00:01:11]>> Joining me now is the host of Interview with a Killer, investigative reporter David Scott. David, wow, what a fascinating way to prep us for this interview. I mean, just seeing the letter that he wrote to you, that is so revealing. Tell us more about this particular interview.

[00:01:30]>> Well, when you interview killers for a living, things don't always go as planned. And and this is one of those cases. In fact, this might be the most curious case we've covered so far. Um, a case of inexplicable patraside, the killing of a father by his son. In this case, the father was a wealthy hedge fund uh founder in New York City. And his son was the golden boy, blonde, 6'5, Princeton graduate, athletic, uh somebody who really had everything money can buy, but he also had something else.

[00:02:03]Uh a history of psychiatric problems.

[00:02:06]And uh and after they argued over over money of all things, uh Tommy Gilbert Jr. shot and killed his father in cold blood. Uh, and nobody has seen or heard from him since. That was more than 10 years ago. Uh, we tracked him down in a prison in upstate New York. And, uh, and, uh, it is a very different interview with a killer, but I think very revealing.

[00:02:30]>> Yeah. Incredible insight that you're able to get from someone who grabbed all of those headlines a decade ago. Uh, I want to play for our viewers some of your interview where you talk about his upbringing and whether or not that has any impact on where we are today.

[00:02:47]>> As you look back, what what does it look like to you that that uh that sort of elite world of, you know, the New York City uh wealthy socialite?

[00:02:58]>> Um, just a normal up upbringing. Um I think uh um just like anyone else would go to school and do uh regular things.

[00:03:07]>> Were you aware of your privilege as you came up?

[00:03:12]>> Um no I don't think so. I think I uh took everything as a fairly normal existence.

[00:03:17]>> Was there anything something that you were missing as you were brought up?

[00:03:24]>> Um no not really. Not really. Usually, this is the easy part of my interviews with killers, but Tommy Gilbert would barely discuss how he grew up and how with great privilege came tremendous pressure. I know that one of the things people don't see from the outside is the enormous expectations put on children in that world. Is that fair?

[00:03:48]>> Yeah. Yeah.

[00:03:51]David, it seems like there may have been some difficulty getting him to answer fully or have long questions. Is that something that you ran into with this interview?

[00:04:00]>> Yeah. Well, exactly. I mean, it's it's not even clear that he's capable at this point of having a conversation. Um, and certainly he wasn't willing to to try very hard. You could see he's his eyes are are shifting around. He's growing more and more uncomfortable. Um, more and more monosalabic.

[00:04:20]um you know the uh the the first part of these interviews is usually the the easy part uh where we just ask them to sort of reflect back on their lives but he would barely engage with me. Um and uh and you know for a decade there's been a debate about uh Tommy Gilbert's mental health. Um is Tommy insane or is he just bad? Is he mad or is he bad? And uh the jury certainly decided that um despite his long history of psychiatric problems, uh there was enough evidence of rational thought in the crime uh to preclude an insanity defense. Well, 10 years on, he does seem like he has slipped further and further into a state of mental unwwellness and um and uh and and we we come face to face with a a killer who is who has descended further almost into oblivion. Um and it's a fascinating window into uh into you know just this intersection between mental illness and uh and criminal liability.

[00:05:27]Um, and I think uh I think the viewers will um will uh will will really u find it very interesting to dissect um what the golden boy has now become.

[00:05:38]>> Oh, really interesting because of course there's so many arguments to be made that there are those who are not legally insane, but that does not mean that they do not have mental health issues, very serious ones that are surrounding this entire case. David Scott, thanks so much for breaking that down for us. I know our viewers are going to really learn a lot when they watch this episode.

[00:06:00]>> You've maintained your silence all these years.

[00:06:04]The whole golden boy gilded rage narrative that took hold in the media.

[00:06:10]You're cast as this 30-year-old spoiled manchild.

[00:06:16]>> Narrative misses a lot of the the facts of the case pertaining to my innocence.

[00:06:19]>> You regard yourself as innocent.

[00:06:23]Interview with a Killer. New episode Sunday 8:7 Central only on Court TV.