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Dicking Around

Gil Whitlock wears a leather jacket and aviator shades. On his website, he poses toughly in front of a black sedan, arms crossed and chin tipped slightly upward. His face, complete with husky moustache, has the jaded, callous glaze of a man who’s seen it all- and perhaps he has. Whitlock is a private investigator, based about 25 miles outside of New Haven in Newtown, Connecticut. Fifteen years ago, armed with several decades of crime-fighting experience, raw determination, and a big dream., he founded Associated Research and Investigations, Ltd.

In person, Whitlock has none of the swagger that one might expect from his digital identity. Paternal, earnest, and instantly likeable, he says things like “silliness” and “gee, that’s cool.” He talks slowly, chewing on his words as though mulling over ways to make his work sound exciting. Whitlock is amicably self-effacing, jovially prefacing his interview with “Pardon me, I’m not a Yale graduate.” His slick website persona and burly credentials-criminal justice major at Western Connecticut State University, military policeman for the U.S. Army-seem little more than a window display. He runs his private investigation business out of his suburban home and speaks wistfully of a childhood spent idolizing the stars of Magnum, P.I., a TV show featuring the glamorous escapades of a private investigator in Hawaii. “I just thought: ‘what a cool way to make a living,'” he remembers.

Whitlock’s dream was once to join the FBI. When he talks about it now, he grows prim and matter-of-fact; he knows everything there is to know about the Bureau, and is proud of it. He knows the feds have a series of exacting physical prerequisites, including restrictions on height. “Short agents don’t project the right image,” explains Whitlock. He launches into a tale of FBI agents caught in a shoot-out after an armored car robbery in Florida. One agent lost his glasses, and, rendered blind and defenseless, was killed while feeling around for his gun. Incidents like these have resulted in the agency’s stringent vision requirement. Whitlock has failed it twice. “So that’s why I didn’t pursue my dream.” He concludes the story with a forlorn sigh.

Instead, he went to work for the sheriff’s department in Fairfield County. Eventually, he attended the State Police Academy in Connecticut and was sworn in as a police officer with the fraud unit in the labor department. “I did not like working for the state,” Whitlock says. “I always had a problem with all the red tape. I spent as much time writing reports about what I was doing during the day as I spent doing it.” He felt all the glamour and romance of his childhood fantasy-high-speed chases, stealth investigations-fading into a relentless bureaucratic labyrinth. Looking to avoid a wearily plodding professional future, Whitlock did some research, talked to some investigators, and decided to venture out on his own. It was a risk, he knew, to abandon the stability of a life nestled securely in the arms of the state. Gil had to turn in his government-issued car upon his resignation. He recalls that the manager of the garage was unable to believe that anyone would relinquish a free car. “He looked at me like ‘are you an effin’ moron?'” says Whitlock.

The licensing process to become a private investigator in the state of Connecticut usually takes about six months. It involves a thorough examination by state police, extensive paperwork, fingerprint submission, and five years of full-time experience as an investigator with a law enforcement agency. Then, explains Whitlock, it’s all a matter of getting your name out there. His meager staff consists of his fianc�e, his son, and a couple of other agents, but it’s clear that the venture is primarily Gil’s own project. His company tackles an array of legal and personal issues. “This is no normal nine-to-five job,” he says with a tinge of bravado.

And unless your business conducts insurance fraud investigations, uncovers relationship infidelity (his website proclaims: “Is your significant other no longer interested in sex? Find out why!”), upbraids deadbeat parents, or uses a polygraph, he’s right. It’s a vast and varied field. “We’re always doing something different,” Whitlock explains. “People want to file lawsuits over the silliest things. These days, everyone is so litigious.”

Whitlock readily launches into colorful accounts of specific investigations-no names included, of course. Once, he got a call from a woman in Israel who had found his site on the internet. She told him that she’d come to him for help because his name meant “joy” in Hebrew, and she was convinced that he would be able to find her mother. She’d been adopted in Canada and believed that her birth mother was living in Connecticut. Adoption cases, Whitlock explains, are difficult, as many of the records are sealed. But in the end, he was able to find the absent parent, who lived just four miles from his home. “Wow, talk about fate,” he says, still awestruck. “That is
just fate.”

Recently, another woman contacted Whitlock with a very different issue. She’d been dating someone new, and though things weren’t serious yet, she had thought they were starting to take off. When her boyfriend asked her to loan him sixty thousand dollars, she agreed. Shortly thereafter, as Whitlock pithily puts it, “he screwed her and took off.” Whitlock has been charged with the daunting task of tracking down the runaway beau.

Often, insurance companies ask him to monitor employees who have allegedly been injured so badly on the job that they are seeking compensation. In such cases, he has videotaped “gravely injured” employees waterskiing, playing 18 holes of golf, or up on ladders painting houses. Whitlock often has to testify in court. Sometimes, people get angry. “You think about the danger,” he says. “But I’m trained to use firearms and I have a gun. I’m a brown belt in karate. And there’s always pepper spray if you need it.”

Compared to Whitlock’s childhood heroes, his investigative tactics are fairly standard: internet research, special databases, surveillance, which generally includes videotaping and following people. According to Whitlock, “It’s all pretty old-fashioned. Being in the right place at the right time. Sometimes nothing will happen all day.” Other days, he says, he’ll be out tailing people, making sure they don’t know they’re being followed. “Tailing someone is really an art,” he adds. Tracking devices are a legal grey area, so he stays away from them. But he does use night-vision goggles and certain specialized cameras, which he describes with boyish gusto as “all the little toys which make it fun.”

Whitlock’s exploits have attracted some local attention. Several years ago, The Newtown Bee ran an article outlining Whitlock’s successful mission to track down the girlfriend of a dead soldier. In the photograph, he poses at a cluttered desk, hands clasped solemnly over mounds of paperwork. With his lopsided smile, button-down shirt, and wire-rimmed glasses, he looks every inch the suburban dad-which, in fact, he is. Whitlock has two sons and one daughter, all of whom are already out of the house. His voice swells with pride as he describes his daughter-she works in a nursing home, “just brightening people’s lives”-his younger son studying to be a surveyor, and his eldest son, who now runs his own private investigation business in Rhode Island.

At 55 years old, Whitlock is salt-and-pepper-haired, somewhat paunchy, not quite the smooth-talking, sharp-shooting FBI agent that he once imagined. But he has worked long and hard at this business of intrigue and inquiry, and has managed to forge a career for himself that is somewhat in line with the aspirations of his youth. His biggest challenge has been competing with national investigative agencies that have a much broader reach and impact. Whitlock’s small enterprise is holding its own, though he worries that competition will grow stiffer. “It’s kind of like how the big supermarkets come in and force the mom and pop markets out of business.” He pauses and exhales, pondering. “But,” he says with a smile, “I guess they call that progress.”

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