This Delaware Private Investigator Is an Insurance Fraud Sleuth

Super Sleuth: At 67, Dorothy Wesley is the oldest working female private investigator in Delaware who owns her own agency.

Dorothy Wesley doesn’t think of herself as a senior sleuth, though she still thrives on the adrenaline rush she’s felt since 1970, when she was a parole officer in Chicago, and years later as an internal affairs investigator for the Illinois Department of Corrections and police corruption was at its height.
Wesley was the only African-American female dealing with such hardcore assignments then. She’s had a knife held to her throat, and was threatened at gunpoint. She worked in an “all boys” club at the time.

“I was used to being around tough boys growing up,” says Wesley, “and my dad always told me to hold my own.”

And hold her own she did. Affectionately known as Foxy Brown by her colleagues, Wesley was a force. She always packed heat. When she assigned law enforcement duties, she got a rush providing security for entertainers like Chaka Khan, Smokey Robinson, the Rolling Stones and James Brown—and she went on tour with the superstars. It was a fast-paced, exciting life, but in 1979, she walked away from it all.

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Wesley spent the next four years earning a degree in Theology. Her law enforcement colleagues said she traded a gun for a Bible.

After marrying and moving to Delaware in 1986, Wesley was ready to settle down and become a housewife, but she got bored. She longed for the career as a private investigator, which more women were gravitating toward. This time, she called the shots and started a firm called Alpha & Omega Investigations, based in New Castle.

Today, Wesley, a grandmother of five, employs 20 licensed PI’s in the tri-state region, but she still enjoys cracking cases herself.  She doesn’t look a day over 50, she wears disguises—once posing as a hooker— and is often spotted wearing an Afro wig or a hat and glasses. Her mini-pin camera is usually hidden in her purse.

Like many private investigators, Wesley tracks down cheating spouses, though these days, she often talks herself out of those gigs. When the producers of the TV show “Cheaters” wanted to hire Wesley, she turned them down.

“Nobody is ever happy in the end, and I just wasn’t interested,” Wesley says. As for the potential clients who suspect their partners of cheating, Wesley counsels them by phone, rather than going for the quick buck. “They thank me later for not wasting their money because they’re either back together or happily divorced,” she says.

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Wesley now hunts down a different kind of crime: insurance fraud. According to Frank Pyle, the deputy director of the Fraud Prevention Bureau for the Delaware Insurance Commissioner, it’s a job Wesley does well.

Pyle recalls a case in which Wesley videotaped a Newark man who was collecting workers’ compensation for alleged back and neck injuries. Records show after visiting his doctor during the day and reporting his pain level at a high level of eight, it was Wesley’s firm that secretly videotaped the claimant that very night at a local roller rink.

“He wasn’t just roller skating, he was roller dancing,” says Pyle. “He was doing things that I couldn’t do in my sneakers, like spins, splits and twists.”

The videotape still makes the staff at the Insurance Commissioner’s office chuckle. Still, Pyle stresses that fraudulent insurance liability and workers’ comp cases are serious business. The National Insurance Crime Bureau reports insurance fraud is a $260 billion dollar a year problem in the United States, which adds $700 a year in health care expenses for the average American family.

“That angers me because our insurance goes up because of them,” says Wesley. “I think it speaks to the moral fiber of how we live now. People are always trying to get something for nothing.”

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Wesley has considered writing a book about her life, beginning with the birth-father she didn’t met until she was a teenager. Even though she wasn’t raised by her biological dad, who was a policeman, Wesley thinks law enforcement is in her blood. She mentors others who want to become private investigators, but has a particular passion for speaking to women about self-empowerment and their spiritual growth.

Asked if she will retire soon, she shakes her head. “No, I love what I do,” she says. “When I walk into a courthouse, it’s like smelling fresh coffee.”

For anyone thinking about filing a false liability or insurance claim, they’d better think twice. One of Delaware’s most seasoned private investigators may be assigned to the case.