New York Magazine – What obsessed Angelo Haligiannis was the bracelet. Every white-collar criminal hates the bracelet. At home with nothing to do, they can’t stop looking at it, fussing with it,trying to wish it away. It was the same piece of ankle jewelry that Martha Stewart wore, the same one she’d joked about having learned how to disable on the Internet. For the fourteen months thatAngelo had been under house arrest at his parents’ place in Manhasset—grounded, essentially, at Mom and Dad’s, while he awaited sentencing—the electronic monitoring device had emitted a tiny radiosignal to record every time he came within 150 feet of a receiver the government had put in the house. Twice a day, as a condition of his bail, Angelo was required to check in by phone with thefederal court’s Pretrial Services division. To make sure he wasn’t really calling from, say, the French Riviera, the Pretrial Services officer would check the bracelet. If the signal was received,all was well; if not, a set of protocols kicked in, starting with calls to friends and relatives and culminating with alerting airports and enlisting federal marshals to start a manhunt.

To someone like Angelo, who at 33 had made it as far as he had in life by mastering the most sophisticated financial game in the history of capitalism, the bracelet must have seemed ridiculously vulnerable—less like the device that tormented Will Smith in Enemy of the State and more like something you’d pick up for your feisty border collie at Petco. The bracelet itself was plastic—“tamper-resistant,” the government called it, but not tamper-proof. There was no command center with a phalanx of military personnel staring at a tiny light blipping on a digital screen, tracking his every move; there was no satellite that tipped off the police if he stepped too far from the front yard. The real weakness was obvious and therefore never likely far from Angelo’s thoughts: the absurd length of time it takes for anyone to recognize that a convict has gone missing.

The government, strangely, doesn’t monitor its home-confined white-collar felons directly or around-the-clock. Instead, it depends on a subcontracted private company to use the bracelet’s signal to draw up reports on every “program participant,” noting every early departure or late return home and each failure to return home after an authorized absence. Those write-ups only come out daily. Until the following day’s report, what Angelo did between his breakfast and dinner phone calls was entirely his own business. Angelo’s prosecutor had warned the judge about this very loophole a year earlier, in an impassioned, failed request to deny him bail: Anyone can cut the ankle bracelet. Anyone with a little money can buy a fake passport, slip into Canada or Mexico, then board a plane for who knows where. Anyone can disappear with an eight-hour head start—gone until dinner before he’s even missed. Most don’t, of course, because in the great cost-benefit analysis of life, the cost of leaving usually outweighs the benefit: There is the near certainty of more jail time if you’re caught, for starters, plus bail and the property put up as collateral behind it, not to mention the loved ones you’re forced to leave behind. The trick, if you decide to flee, is not minding the consequences—having, perhaps, an unhealthy appetite for risk.

January 10 was supposed to be Angelo’s last day of freedom, the day before he was expected to be sentenced to at least fifteen years in a federal prison. That morning, he awoke in Manhasset and made his usual call to the federal monitoring center before eight o’clock. Shortly after he hung up, he drove with his father, Vasilios, to his father’s welding and ironworks company in Maspeth, Queens, where the court had allowed him to spend some weekdays. He was expected home at four-thirty or five.

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