I was bail bondsman for Jay-Z, Conor McGregor, and Harvey Weinstein. Here are 5 things powerful people realize when they get their GPS-monitoring ankle bracelets

• As a high-profile bondsman, Ira Judelson fitted hundreds of powerful people with ankle bracelets.
• "Everyone feels a little violated," he says of the lawyers, doctors, and Wall Streeters.

This is an as-told-to essay based on a conversation with Ira Judelson, who over the past three decades has handled the bail arrangements for such high-profile criminal defendants as Lindsay Lohan, NFL stars Plaxico Burress and Lawrence Taylor, and rappers Jay-Z, Lil Wayne, and Ja Rule. He also fitted Harvey Weinstein with the GPS-tracking ankle monitor the disgraced movie producer wore for two years.

Here are the five things Judelson says his most high-profile clients realize after being fitted for the GPS ankle monitors, a device worn by some criminal defendants who are released from jail pretrial. The essay has been edited for length.

1. A team of actual human beings is tracking your ankle bracelet and knows where you are at all times.

When criminal defendants get their GPS ankle bracelet, everyone feels a little violated. They feel constricted. They feel not in control. They feel like people are watching them and know where they go and what time they go there. And that's all true. It really is a GPS-tracker, and I have a team of monitors who are watching where every bracelet is at all times.

I've done hundreds of bracelets over the past three decades, for doctors, lawyers, for a lot of so-called people of power who work on Wall Street. Powerful people have the most problem with that — with being watched, and being told where they can go and where they can't go. Because they're not in power.

We also set up what's called exclusion zones within the areas they are allowed to be — we don't let anybody who's on a bracelet anywhere near an airport. The device I use for my clients will basically start talking to you and say, "You are near LaGuardia Airport — get away. Get away. You are in a danger zone."

2. Ankle bracelets are ugly and feel like a clunky radio is strapped to your leg.

For two years, Harvey Weinstein was confined to Connecticut, where he had a home, and New York, where his office was.

(In 2018, a Manhattan judge ordered Weinstein be monitored pending trial on charges he raped one woman and committed a criminal sexual act on a second woman. Judelson handled Weinstein's ankle bracelet, and wrote the bond when the disgraced movie producer's bail was increased from $1 million to $2 million. Weinstein's 2020 conviction was upheld on appeal in 2022; he is serving a 23-year sentence.)

I put the bracelet on Harvey. He was telling me as the bracelet was going on how uncomfortable it was, and asking what are the requirements here, and how strong is this bracelet. What do I have to do, can I call you at any hour of the night. Just a lot of questions.

He was not very happy. He was a client who was not very used to having anyone dictate to him what needs to be done. He's always been a man of power. I think he felt very uncomfortable and maybe very vulnerable as that bracelet went on.

I think you get used to it. And it's definitely better than being in jail. But at first when you have it on, and you're walking around, and you feel something heavy on your ankle, it's not a great feeling. It's like you're carrying a radio around on your ankle. It might be an embarrassment. And it's also a reminder that you're in trouble.

3. Ankle bracelets, diabetes, and high blood pressure do not go well together — just ask Harvey Weinstein

Harvey had a lot of medical issues. He had diabetes, and high blood pressure, and his ankles swelled up. And obviously, when you're on the bracelet, if your ankle swells up it gets very uncomfortable.

My monitoring team would call me, and say, you know, Harvey has an issue.

So we had to swap out the bracelet a couple of different times. For the earlier bracelets, they had the iron-clad one, which is iron around the ankle. Then later on, they came out with a rubber strap, which was more comfortable.

In my eyes, the strap has to be snug. With the rubber strap, you could put a thumb in there, and that's ok. With the metal, if they could put their thumb in there, I didn't like it. I have skin in the game. I have a very big bond I could lose. I wanted it to be tight.

I would send my team there to Harvey in Connecticut, to his house in Westport. We'd have to unscrew it if it was metal, and if it was the rubber one we'd cut it off. And either way we'd alert the monitoring company that we were cutting it off and putting it back on.

4. You have to recharge the thing every day

The biggest problem when you're wearing our ankle monitors is you have to charge them every day, at least once a day, which means staying in one place for a couple of hours while it's plugged in.

If you don't recharge it, and it goes dead, it sends an alert right away to the person that's monitoring it. And then they think that there could be something going wrong, and a defendant could be trying to flee.

I did one in Brooklyn for an Orthodox rabbi, and it was a $2 million bail on a high profile case with a sexual charge.

(That client, Baruch Lebovits, was sentenced to two years prison on a 2014 plea to felony sex offenses with a minor.)

And the rabbi was on an ankle bracelet. And I had to make sure he charged it on Fridays before the Sabbath began at sundown.

We get these frantic calls at one in the morning, you know, that the bracelet, the red light's going on. And 95% of the time it's the battery's dying. And the battery dies for a lot of reasons, but almost always it's because the battery hasn't been charged.

5. Ankle bracelets are not indestructible

I did have a client that slammed a bracelet. This was a Wall Street client that was going through a revolving door. And he must have damaged the bracelet in the door, and it set off an alarm to us, but he didn't know that.

And then I was getting the alarm, and I couldn't get ahold of him. I called the family and kind of threatened them.

And they were like, he's at work. Within 20, 30 minutes, we got ahold of him. We realized he got it caught in a revolving door. And then obviously we had to send somebody down there to fix the bracelet. In the end, we had to swap it out. The technology is always improving, but it's not perfect.

I've had clients that have been on the bracelet for a couple years. I have a couple of doctors in Brooklyn that had Medicaid malpractice cases with the state attorney general's office from before COVID.

And the judge ordered bracelets, and I put them on them. And then COVID. Everything got backed up two, three years, and the guys are still on them.

But I think if you gave someone the choice of whether they'd want to be in jail or be on an ankle bracelet — the answer is always that they'd rather be on an ankle bracelet. One hundred percent.