Private Investigator and former Peekskill resident Ed Webster is featured in the current Dateline Podcast, “The Thing about Helen & Olga” hosted by Keith Morrison. His widow, Diane reminisces about the man and the fascinating case.

Gumshoe. The word conjures up the image of a tough, tenacious, doggedly determined Private Investigator—colorful characters like Sam Spade in the movie The Maltese Falcon, or Jim Rockford in the ’70s hit TV show The Rockford Files.  

Ed was the quintessential P.I. Although he had an office in Manhattan, one block south of Canal Street in Chinatown, he often worked out of his home in Peekskill. Licensed to carry, he strapped an ancient Smith and Wesson .45 to an ankle holster, hidden by his signature cowboy boots, before he left for work each day. He even had his suit jackets cut and tailored a certain way to obscure his gun if he wore it on his belt. In his 40-plus years as a P.I. he never had to use his weapon—he always managed to defuse a tense situation with humor.

Ed not only looked the part, he lived the part. Today, when almost everything is done on a computer through the use of databases—from background checks to financial statements, employment searches and criminal records, Ed was about as old-fashioned as a P.I. in a noir film. He believed you had to hit the street to get the real story. Like a classic gumshoe, he pounded the pavement, knocked on doors, peeked in mailboxes, talked to neighbors, sat endlessly on stakeouts observing the comings and goings of a “subject,” worked the phones and scrutinized written records with a fine-tooth comb.

In 2007 Ed was working for MONY (Mutual of New York) as the Director of SIU—the company’s Special Investigations Unit. His job was to investigate multi-million-dollar insurance fraud cases—people who faked their own deaths, or husbands/wives who killed their spouses for big insurance policy settlements. The “Killer Granny” case, as Ed referred to it, started out as a routine assignment to cross-check details on the policy to see if they jibed with the facts surrounding the death of the insured person.

At first blush, it appeared to be a straight-forward, open and shut hit-and-run case. A middle-aged man, ostensibly changing a flat bicycle tire was found dead in a back alley behind a Los Angeles strip center.  After reviewing police and autopsy reports, visiting the site, talking to shop owners and viewing video tapes from a camera positioned in the alley, Ed’s hackles went up. Something just wasn’t “right” with the scene. When he reviewed the insurance policy, he knew something wasn’t right.

Information gleaned from the policy indicated that the insured was a key-man in a local business – and was the fiancé of one of the partners. Ed snooped around and found that the business address was phony; the business didn’t exist, and there was something “off” about the fiancée—one of the beneficiaries of the insurance proceeds.

Further investigation revealed the victim was a homeless man who frequented a soup kitchen in LA’s Bowery District, and there were two little blue-haired ladies in their 70s “helping” men by offering them a place to stay and some money for living expenses. It was hard to believe, but Ed came to the conclusion that the women, Helen and Olga, had fashioned a diabolical scam to target a vulnerable victim, gain his confidence, and then kill him for the insurance money.

Ed built his case and took what he found to the LAPD and suggested that this might be a homicide for profit, not an accident. It turned out that years before, another homeless man was found dead in an alley, and the beneficiaries of his substantial life insurance policy were Helen and Olga. That incident ended up in a “cold case” file—until Ed’s investigation prompted the police department to take another look and connect the dots.

Ed worked closely with the LAPD and the FBI to catch these cold-blooded killers, who were ultimately convicted and sentenced to life without the possibility of parole. Their story, and Ed’s participation in bringing these women to justice, was featured on an episode of Dateline, and is now a six-episode Podcast, “The Thing About Helen & Olga,” hosted by Keith Morrison.

Ed passed away in 2019. The legacy he leaves behind goes far beyond his talents as an investigator. He was a beloved husband, father and friend.

Diane Webster was the publisher from 1999 to 2000 of the print edition of the Peekskill Herald.