An Interview With Westchester County Court Judge James Hubert

Judge James Hubert was first appointed to the county bench in 2007 by then-Gov. Eliot Spitzer. Since then he has presided over hundreds of criminal cases, from murders to low-level possession of drugs. Below is an edited and condensed version of an interview conducted last week in Hubert’s chambers. He was first asked about his particular judicial style — which includes a fair amount of stern lectures from the bench. The conversation also reminded him of a prior defendant who came to court wearing a T-shirt emblazoned with a large marijuana leaf. The accompanying profile can be found here. — Erik Shilling 

NOTE: Ellipses indicate portions of the interview that were edited out for clarity and flow.

JUDGE JAMES HUBERT: I don’t think I’ve met anybody who’s happy to see me under the circumstances. I don’t really think that that’s the case. I would say that I personally feel that it is important to speak to individuals that are before me, for two reasons. […] One is, to impress upon them the nature and gravity of their situation, and, number two, to impress upon them that they are being called to account for their actions, assuming they’re guilty. Depending on the state in the proceedings it will be couched in the appropriate way.

A lot of times that I’ve seen you it’s been after. They’re there for some probation violation.

JH: Of course. We already know what you did. Now it’s what’s going to happen going forward and why are you in trouble for what you did. I consider those things to be what I call teachable moments.

I think Obama uses that phrase.

JH: He’s not the only one. He didn’t make it up; that’s for sure. He didn’t make it up. I do consider them to be teachable moments. I go back to when I was a kid. Teachers, various people, parents, various people had a definite ability to impress upon you the seriousness of your situation and how important it was for you to change your approach, adjust your attitude, embark on a different course, whatever. So I think that it’s part of my job to make that impression on them if I can.


JH: I had a mother not very long ago. I was at the supermarket, and she walked up to me and she introduced herself and she said, you know, “Judge Hubert? You’re Judge Hubert aren’t you?” Words to that effect and I said, “Yes.” She said, “You don’t remember me.” And that’s when I usually start to get a little nervous, because I’m not good at remembering most people. I was scrolling through my memory banks there. Then she said, “My son was in front of you.” Then usually I find out exactly where this is going. She said to me, “You sent him to jail.” And I’ll try to say, “I’m sorry, please tell me your son’s name.” I’ll try to see if I can wade into it somewhat slowly, figure out where this is going. They’ll answer me and tell me and, whenever this has happened — and it’s happened, I’m going to say a good dozen times or so — the feedback is always the same, which is, in summary, you spoke to him in a way that no one’s spoken to him before. The general thing is, he did the time, and he’s a changed person. He’s much different now. And he’s really taken to heart everything you’ve said.

I had the clerks tell me once, and one of the kids, he walked in, and it was a bail situation. He came in with like a marijuana shirt on, with like a big leaf of marijuana or something on the front. I forget what it said, but it said everything other than, “Arrest me because I’m selling marijuana.” It said everything else on it. And I said to him, I said, “Why don’t you have ‘Arrest me’ put on the back of your shirt?” I said, “Because you may as well because that’s what your shirt is telling police.”

You made a decision when you woke up this morning to wear that shirt.

JH: Yeah, you made a decision to wear that shirt and you’re telling people, whether you believe it or not, you’re telling people about yourself. And I said, “So, you shouldn’t be surprised that you’re arrested because, after all, your shirt just about tells people, tells any person who’s a police officer, that there’s just the possibility that you might have marijuana.

That might be probable cause.

JH: [Laughs.] I don’t know if it’s probable cause, but it’s certainly a big step along the way. OK? Let’s be clear about that. And I said, second of all, I have to decide whether to let you go home or send you to jail. I usually say to them, I say, “Have we ever met before?” And I say, “That’s a good thing, but now you’ve met me. I don’t like to draw assumptions about people when I first meet them so I’m going to give you a chance. I’m going to send you home today. Now you’re going to have to come back tomorrow. You’re going to have to do one of two things. You might not come back tomorrow and I’m going to have to issue a warrant for you is what’s going to happen. Or you’re going to come back tomorrow, which brings me to the second part of this. If you come back wearing that shirt, then I will know for a fact that you want to sell marijuana; that’s the career path you’ve chosen for yourself. I will know that, because you’re telling me, and I’m going to set bail on you, because I can’t rely on you to stay out of trouble.” And so the kid came back the next day in a suit and a tie. And his mother was sitting in the back, and she was sort of like, “He’s here,” said, “Remember him?” So when he came up, I told him, I said, “You’ve changed your clothes.” So we went over what I had said, so I said, “I’m going to take a chance on you. I’m going to release you. You’re going to have to come back to the courtroom but you’ve proven you can change.

You’ve shown a small ability that you can listen.

JH: Yeah, you’ve taken a first step. And I said, “But I’m telling you right now, you screw up, you’re going to jail. Do you have any reason to believe I’m kidding you? Do you have any reason to believe I’m not serious? You may, but you can try.” And so the clerk came back to me later and said that he was out in the hall and he was yelling at his mother. And I said, “What was he was yelling at his mother for?” He said [the boy] said, “If I had a father who talked to me like that I wouldn’t be in this trouble that I’m in.”

Hubert outlines a stump lecture before discussing the limits of such lectures and, more broadly, the criminal mind.

JH: I’ve had a lot of mothers and fathers come to me, and one of the things I typically say to them, especially if [their children] are locked up. They’ll come to me to make a bail application, and I’ll have to make a decision about that. And I always ask them, “How’d you like being in jail?” And they say, “I didn’t like it.” And I say, “Don’t shake your head. Don’t tell me you didn’t like it, because I’m looking at your record here and you’ve been in jail quite a bit. So let me ask you a question. Do you like Brussels sprouts — the vegetables? They say, “I don’t know.” And I say, “I don’t like Brussels sprouts. I don’t like them. And I don’t eat them. If you put Brussels sprouts in front of me I won’t eat them, because I don’t like them and I know I don’t like them. And, you know, I think I’m like most people. If I don’t like something, I don’t do it. On the other hand, I like ice cream. If you put ice cream in front of me I’m going to eat it. I’ll eat it even when I’m full. The impression clearly will be that I like ice cream. So, I mean, if you don’t like, why do you keep going back?”

It’s funny. I’m not saying that people don’t think of it that way, but it’s odd to look at their expression when I say that to them, because what are they going to say at this point? Because they can’t deny that they’ve been to jail a lot. And it’s logical to assume that if somebody keeps going back to jail they might like it. So, they’re kind of stuck in a moment of self-reflection. Now, not everyone responds. Some guys get tough on you, get this real tough look. But others get, like, maybe you have a point. I have no idea whether that will ultimately dissuade them. But I think they do begin to try to at least get them to think about their behavior, think about why it is they’re in the situation they are, because there is a tendency among people to rationalize whatever their situation is. People don’t typically blame themselves for what happens to them. And sometimes it generally isn’t your fault. Sometimes people go the opposite. They blame themselves for things that are not their fault at all. But I think people also go in the other direction.

A lot of them are low-level, and at this point, at least, they’re not true criminals. They’re not people I see over in federal court.

JH: You’re not going to talk to a mobster like that. They don’t care. They’ve made decisions about their life long ago. When I have older people with long criminal records — oftentimes substance abusers — I’ll ask them, “How old are you?” I try and prick their conscience. “What do your kids think of you? Your kids will remember everything you did or didn’t do. They will say, my father always had my back. Or they will say, my father was never there for me. It doesn’t matter. That will happen. You’re going to have a legacy. Do you care what it is at all? You know, you’re getting kind of old now. Are you going to spend the rest of your life in jail? Because you’ve spent a great part of it there.”

And I’ve had one or two, you know, I’ve had the attorney come back and tell me, he walked out of there, and he went over to the center and signed up. He’s going into rehab. I didn’t tell him to do that, I didn’t require him to do that, he just did it. And I saw this one guy, he kept coming back to court, kept coming back to court. And over the months he appeared before me his appearance really changed. He dressed better. He shaved. He cleaned himself up. He looked better. And he was very proud to tell me that he was trying to change his life around. I don’t know whether he ultimately did or not. My belief is that, if you talk to them, some of them will listen to you. I think that is part of my responsibility.

Some other judges, it’s like you’re going shopping, and you’re just moving people along through the system and you’re the checkout guy.

JH: It’s easy to just punch people’s ticket. And that’s all you’re doing, you’re punching their ticket. My own personal approach to it is really based on the years that I spent practicing.


You can’t save everybody. I don’t measure it that way. My attitude is, maybe 10 drown but if I save one, or I can reach one, that’s one more than it would’ve been. Some of my approaches, it’s the Wizard of Oz, that’s what it is. So there’s the Wizard of Oz. There’s Dorothy and the scarecrow and the tin man and the lion cowering before the great and powerful Oz. And there’s lightning and thunder and bombast and there’s, you know, “Silence!” Oz has spoken! Meanwhile, the guy who’s Oz is this guy behind the curtain. So to me, the robes are like the curtain. The robes are on and you see this disembodied head of the great and powerful Oz. No robes, and here I am. So who is the person behind the robes? That’s who I am. You can look at the story of the whole Wizard of Oz and you can say, Dorothy became a much better person.  The lion found courage. The tin man found a heart. The scarecrow found a brain. The wizard scared the shit out of them, sent them off on their journey, and they found themselves.  And they came back better people.

Whether they know whether it’s real or not, it doesn’t matter.

JH: Yeah, you know, is it real? Is it theater? Can it have a positive effect? I believe so. It can, as long as you don’t make it to ridiculous. Every once in a while my staff says, “Listen, you gotta dial it back.” You were doing fine up until that last little lit bit you throw in there.

Some of the court officers groan.

JH: I get the eye-rolls. Some of them like it, some of them don’t.

At another point in the interview I brought up perhaps Hubert’s most high-profile time as a private practice lawyer, in 1994, when he represented Jeffrey McClain, who accused Pelham police of roughing him up and calling him racial epithets while he was in custody. Hubert at first dimly remembered the incident, before launching into the story of the case, in vivid detail. The case was closed in 1996 after both parties reached a settlement.

JH: That’s a blast from the past. What happened to him? He got beat up in Pelham. It was ultimately settled — he died. He died during the pendency of the case. He was on his deathbed and they had offered to settle the case. It was clear he was not going to make the trial date. And he told me to settle the case, and I settled it. As he put it, “Just get enough to put me in the ground and get a little for my kids.”

He had been charged with possession of a controlled substance —a Class A misdemeanor in New Rochelle. And he didn’t show up for court. I wasn’t his lawyer [then]. And they issued what was called a bench warrant for his failure to appear. And then one day, he was staying at his father’s place which was on the border between New Rochelle and Pelham, and he walked down the street, crossing from New Rochelle into Pelham, and the cop rolls up to him — the Pelham cop rolls up to him — and he says, “Are you Jeffrey McClain?” And he says, “Yeah,” at which point [the cop] says, “Come here,” and Jeff says, “No,” and runs away, runs back into New Rochelle, hops over a fence or something like that and runs into his father’s apartment, and hides under the bed. The Pelham cop calls New Rochelle, because he can’t make the arrest in New Rochelle and New Rochelle comes, and they all go in, and they arrest him.

What got the legal action going was two things. First and foremost, New Rochelle, instead of taking him back to New Rochelle on the warrant, and bringing him to the judge on the warrant, and doing whatever they were supposed to do, lock him up, whatever they were going to do, they give him to the Pelham officer to drive him back to Pelham.

Probably because he was steamed that he didn’t get him originally.

JH: That was certainly true. But, even if they would’ve arrested him and transported him to the Pelham precinct, New Rochelle would’ve still needed to bring him to New Rochelle. He was going to end up in New Rochelle one way or another. There was nothing to clear. He hadn’t violated the law in Pelham.

He had run away from the cop, though?

JH: Maybe, maybe. But here’s the thing, they go back to the Pelham station house and they take him inside. He’s not charged or booked with any offense in Pelham. And the cop takes him into the back, and, according to my client, he is beaten up. He ended up in the hospital for three days.

Or, they would say, that he beat himself up.

JH: They said he injured himself when he was running away because they say he vaulted a fence and hurt himself and fell. That’s how he hurt himself. The problem is, is that when he was brought in, the duty sergeant or the duty officer that was at that desk was talking on the phone to a woman who was complaining about a barking dog. And everything on the phone is recorded. You can hear him talking to the woman about the barking dog. He’s obviously very bored. He doesn’t want to deal with it. And all of a sudden, you hear shouting in the background, and he says, “Hold on, hold on,” and he puts the phone down, and the line is still open. And you can hear what sounds like someone getting beat up, and you can hear the Pelham cops say, “That’ll teach you not to run from a Pelham cop.” This is all recorded.

So then they take him to New Rochelle, and when they get to New Rochelle, the New Rochelle sergeant won’t  take him. They say, we ain’t taking him. He directs that they send him to the hospital, because they don’t want any responsibility for his condition. So they refuse to take him. He’s ultimately taken to the hospital, and then he’s just released. Now he finds me and he hires me. I have no idea how he found me. I don’t remember that.

Drug possession charges against McClain by New Rochelle police were also later dropped.

JH: He told me, “I know I’m not guilty of drugs.” And I’m looking at him, like, sure go ahead, tell me why you’re not guilty. Sure. I’m not busy today. And he said, “Because it’s beat stuff.” He said, “I sell to the stupid teenagers, cocaine, but it’s not cocaine. It’s nothing. It’s beat stuff. I’m just beating them out of $10. That’s all I’m doing. I said, “Oh.” So I call them up, and I said, by the way, do you have a lab report on the thing. They were snarling at me. “Is this Jeffrey McClain? We know him.” I said, “No, no, please, just look.” And sure enough, they had it before the warrant was even issued. And it said no controlled substance. It was nothing.

Possession of flour is not a crime.

JH: Possession of flour is not a crime. All he was charged with was possession. He was never charged with a sale, according to the police. They busted him because they knew it was Jeffrey McClain. That’s why they busted him. So it turned out that they never should have issued the warrant in the first place, because there was no controlled substance.

The whole thing should have never have happened.

JH: The whole thing should never have happened. So that’s what ended up. The center of the lawsuit, of course, was him being beat up … I was told by somebody, I’m not sure who, that the cop who beat him up had been in a prior incident. I think I found out subsequently.

Those guys, it’s never the first time.

JH: I’m not 100% sure on this.

Too much of a risk.

JH: At some point when you start to actually cost them money — it’s one thing when you’re doing it and it’s not costing us anything, but when it starts to cost us money, now it’s a problem.


JH: And then he passed away. He passed away.

He was an older guy?

JH: He was middle-aged. I won’t tell you what he died of, but he had a drug problem, you can read between the lines. I didn’t even know that he was. One day he just called me up and said, “I’m in the hospital.” And said, “What the hell are you doing in the hospital?” And he said, “I’m dying,” and I said, “What?” You’re working on stuff. Sometimes you’re working on his matter sometimes you’re working on other stuff. You figure, OK, this is fine. That’s stable. I don’t have to deal with this for the moment, and, all of the sudden, something out of left field happens. What the heck?

At another point, Hubert discussed a former client in the Bronx who was emblematic of the limits of the legal system. Efforts to locate the woman this week were unsuccessful.

Do you have any judges that are role models, back then or even recently?

JH: [State Supreme Court] Judge [William] Donnino had a lot of compassion. To me he was way too preachy, even for my standards, you know, and people might differ about that. I thought he went a little bit too much. He was much more, how shall I say it, papal, in the way that he talked to people. He reminded me of a priest. I try not to lecture in that way, but I thought that he genuinely cared about it. And I had a client once, and I had her a number of times over the years. I caught her initially when she was 15 years old. She was a co-defendant on a robbery case. She was the, um, Bonnie — not even the Bonnie to Clyde — there’s another movie, which I saw on TV recently. It stars Martin Sheen as this guy and Sissy Spacek.

Yeah. Terrence Malick. “Badlands.”

JH: “Badlands.” Yeah, there you go. She was like Sissy Spacek.

The innocent tag-a-long.

JH: Innocent, although she had managed to do a lot in her innocence — very malleable and very moldable. And I was specifically asked by Donnino to represent her because he wanted to try and work with her. And she had had a horrible, horrible upbringing.


JH: Yeah, but it was even worse. The worst of it was that her father, her parents were in bad shape. Her father had walked out of her life for a long time. Her mother had a lot of family court issues, and had lost custody of her, and whatever. But we tried to put something together for her, and it worked for awhile, and then she fell back into bad times, and he called me back again, and I represented her again, and we tried more things, and this time we really seemed to get her up and running. She got back on probation. She was doing well. I would run into her coming out of the courtrooms at random times. Most times she’d be coming from her probation officer. And I remember at one point, she was very proud of herself, she had gotten some certificate or something. She was very proud of herself. And I thought that she was doing really well. And then I just happened to be doing arraignments one evening. I used to do a lot of indigent defendants stuff.

You were doing Legal Aid?

JH: It’s what they call 18B. I would do 18B. It wasn’t all I did. It was a very small part of my practice. But I would do it because it was something that I didn’t mine doing. So I was doing arraignments. Every once in a while, couple nights a year, they’d schedule you for arraignments, and you’d be there for 8 hours, catching cases, just representing people. Sometimes you’d keep them as clients, sometimes you wouldn’t. And all of the sudden they brought this woman out, and I was standing nearby. It wasn’t my case, and she looked at me, and she said, “Hi, James.” And I realized it was this girl. She looked awful, just awful. And I asked the attorney, I said, “I used to represent her. Do you mind if I just talk to her?” Whatever. He was like, “Yeah, go ahead,” and I talked to her and she was in horrible shape. What had happened was — the story she had told me was — she had gone back to living with her father, but her father had reacquired an old heroin addiction and was in for a lot of money to some dealer, and, basically, they threatened to kill him. And so he told the dealer that his daughter — meaning her — would work the money off. And she got beat up. They came and got her and they beat her up. They really abused her. They got her strung out. She was there for prostitution.

How old was she at that point?

JH: She was probably in her 20s at that time. This was probably more than 7 years after I had met her. I felt so bad for her. But she was very, you know, “Don’t feel sorry for me. You really tried to help me.” She was very appreciative in her own way for what had happened but she was just gone. She was gone. She had changed her name. She said, “I don’t go by that name anymore.” She was just gone. I remember I saw Donnino months later and he was just, “Wow.” And we talked about it for awhile. That’s the problem. You can’t — some people are just too far gone. They’re just too far gone.

Erik Shilling