HALIFAX, CANADA — The phenomenon of a “black widow” killer — a woman who murders a series of husbands or romantic partners, often to slip off with their fortunes — dates from time immemorial.
Naturally, such deviousness has taken on new power and prominence in an age of social media and dating websites. Still, it took a particularly sweet looking, elderly Canadian grandma-type to truly earn the moniker, the “Internet Black Widow.”
On May 16, 2017, Shepard celebrated her 82nd birthday — a luxury not possible for her second and third husbands, one of whom she was convicted of killing, the other of whom she remains suspected of doing in. Husband #4 almost didn’t make, either, but that was only a case of attempted murder (somehow, her first marriage ended in divorce).
In addition to the wealthy men of means who curiously seem to expire (or come close) while in her company, Shepard spent the years between 1977 and 1991 in and out prison on more than 30 convictions for fraud.
The criminal run of Melissa Ann Shepard has proven so outrageous — so far — that her story has been featured on two separate Investigation Discovery series: first, on the Deadly Women season eight episode “For the Money, Honey,” and again in 2017 on the program, Web of Lies. That’s no small achievement (nor is it one to be encouraged).Related: Broken Hearts and Body Parts — Black Widow Serial Killer Belle Gunness
The killings began in 1991. The same year Shepard did her last stretch for running a scam, she did in her second spouse, Gordon Stewart, by running him over with a car — twice.
Afterward, Shepard told police that Steward had raped her and the “accident” occurred while she was attempting to flee. She ended up doing two years of a six-year sentence, getting sprung early for good behavior.
Shepard next met Robert Friedrich on a Christian dating site in 2000, and the pair quickly wed. He died from a suspicious overdose in 2001, leaving his considerable estate to his new bride.
Friedrich’s sons filed a criminal complaint against their allegedly wicked stepmother, but authorities never produced enough evidence to charge Shepard with the crime (the sons did, however, get a financial settlement).
Cruising still more online dating outposts in 2005, Shepard hooked up with Florida resident Alex Strategos. He landed in the hospital six times with unexplained excess tranquilizers in his system while Shepard looted his bank account.
Police could not pin the tranquilizers on Shepard, but she did go down for grand theft and forgery, and headed back to jail for five more years.
Finally, in 2012, Shepard pleaded guilty to the attempted murder by drug poisoning of 75-year-old Fred Weeks, the fourth lucky fellow to take her hand in matrimony. Shepard’s plea deal knocked her stint down to just three-and-a-half years.
Among the conditions of that plea, however, was that Shepard could under no circumstances access the Internet. Regardless, in 2016, she got busted going online at the Halifax Central Library. She faced charges of breaching her agreement, but, citing insufficient evidence, prosecutors dropped the charges.
Remarkably, today, Melissa Ann Shepard is a free woman. After she last walked out of lock-up, police issued a High Risk Offender Notification. She also signed a “peace bond” requiring her to officIally report news of any new romantic connections. Canada’s Chief Justice Joseph Phillip Kennedy even warned the public: “People who have contact with this woman should be careful.”
All that seems like the polite Canadian way of saying, “If you see this sweet old lady coming your way — RUN, eh?”
Main photo: Melissa Ann Shepard mug shot [Halifax Regional Police]