Margaret McLean, a former assistant district attorney in Lawrence, Mass., and a Boston College professor, has interviewed dozens of career criminals while researching her upcoming book on Boston crime leader Whitey Bulger, Whitey On Trial: Secrets, Corruption, and the Search for Truth (out in February). “I became close to people who had dealings with (Bulger) over the years, which included people in the Italian mafia and the Irish mob,” she says. And the one thing they all had in common? They weren’t about to be lured into an email conversation. “They never provided information over the phone, text, email, or social media,” McLean says. “They know the government has easy access to their phone and Internet records, and will use it against them in court.”

This self-preservation logic is apparently something that never occurred to Bridget Anne Kelly and David Wildstein, the two now-unemployed associates of New Jersey Governor Chris Christie at the center of Bridegate.

It's kind of ironic that for all the ink spilled (or HTML formatted, whatever) trying to explain the scandal, it was Christie who summed it up best. In his almost two-hour mea culpa earlier this month, he did a lot of finger-pointing and backpeddling and almost-apologizing-but-not-really. But he really hit to the heart of the scandal when he described the shocking behavior of his former employees—who apparently plotted by email to shut down Fort Lee’s access to the George Washington Bridge—with two simple words: “Abject stupidity.”

Are there better words for it? Can anyone in 2014 can claim ignorance that an admission of guilt in an email or text might someday be used against you? Feeling sorry for Kelly and Wildstein—or any of the twenty people subpoenaed as part of an ongoing investigation—is like feeling sorry for a relative who fell for that Nigerian prince email scam.

And yet it keeps happening. Over the past decade, incriminating emails with details on every sort of crime, misdeed or poor judgment have invariably ended up on public display. Traders have bragged about price-fixing, Google employees have brazenly claimed that they can make phone manufacturers “do things we want,” stock analysts have made underhanded deals to get their kids into top nursery schools, and big oil insiders have tried to manipulate research on oil spills they caused. Last September, racist emails written by the vice president of a national security firm—whose clients include tennis’s US Open—were leaked to the press. The guy called African-Americans “scum-suckers” and “worthless” and discussed training a new attack dog with “n***er eating exercises.” The former employee who shared the emails might as well have been talking about all email and text scandals when he gave this quote to the New York Post: “How stupid do you have to be to put this in writing?”

Which brings us back to Bulger. Boston’s most infamous mobster, inspiration for Jack Nicholson’s ruthless psychopath in Scorsese’s Departed, was sentenced in November to two consecutive life sentences (plus five years for machine gun charges). But before his capture and conviction, he thrived for decades, and some argue he survived as long as he did because he was overly cautious with every interaction. “Bulger knew better than to conduct illegal business over the phone, at home, or in restaurants due to potential wiretaps,” McLean says. “He avoided self-incrimination by taking long walks with trusted associates. Even in court this summer, he covered his face with a legal pad when he consulted with his lawyer.”

And it’s not just Bulger—you’re not going to find many mafia bosses or drug lords kicking themselves for an over-sharing email.  “It’s only amateurs who believe their electronic communications are confidential,” says Howard Abadinsky, the author of books that sound like the titles of TV crime dramas, including Law and Justice and Probation and Parole. He claims that even criminal organizations that operate transnationally, like Colombian and Russian, rarely use email. Instead, they use pre-paid cell phones “purchased by the dozens and quickly discarded,” or that old standby, face-to-face communication.

Why are gangsters and career criminals so much more tech-savvy than people with business degrees? Is it arrogance? Is it intelligence? Dr. John Suler, a cyberpsychologist at Rider University in New Jersey, thinks that white collar criminals might just be more susceptible to the illusion of “perceived privacy.” Although our rational minds tell us that anything sent via phones or computers are being recorded and available to anyone with the skill to retrieve them, “on a more subconscious and emotional level,” he says, “we perceive text messaging and other forms of online communication as private conversations. When we look into our phones and computers, and into the little boxes into which we type our messages, all our senses are telling us that we are inside a little box—in fact, a box inside a box—which feels like a private, personal space.”

McLean has another theory on why you’ll never catch a Gambino gang member with an email inbox full of confessions: “White collar guys don’t consider themselves criminals,” she says. “They think of themselves as successful businessmen who bend the rules and cut corners to achieve an advantage.” In essence, it’s the false perception that actually, you’re one of the good guys—and this has all been just one big misunderstanding.