‘Black Widow’s’ ex-boyfriend warns men as she gets out of prison: ‘Watch out’

Click to play video: 'Nova Scotia’s ‘Internet Black Widow’ set to be released'
Nova Scotia’s ‘Internet Black Widow’ set to be released
WATCH: Melissa Ann Shephard, known as the "Internet Black Widow" gets out of prison Friday with a long list of conditions. As Ross Lord, authorities aren't convinced the so-called "Internet Black Widow" won't reoffend – Mar 15, 2016

Melissa Ann Shephard, an 80-year-old woman dubiously nicknamed the “Internet Black Widow,” is out of prison once again.

But one of her ex-boyfriends and former victims believes her third stint in prison probably hasn’t changed her ways.

Alex Strategos remembers all too well how he struck up a friendship with the then-73-year-old Shephard, a woman he met on the Internet in late 2004, and whom he believes drugged him as she swindled him out of $20,000.

Melissa Ann Shephard was released from a Nova Scotia women’s prison Friday. Halifax Regional Police warned Halifax residents the 80-year-old is a high risk offender and must abide by a series of conditions. Handout via Halifax Regional Police

It was late 2004 and Strategos, then known as Melissa Friedrich, reached out to Strategos through a website called They hit it off. She moved in quite soon after and began taking care of him.

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“Well, I thought she was,” Strategos said from his home in Pinellas Park, Florida. He laughs as he recounts that. But after Shephard moved in, he said, she began spiking his ice cream with the tranquilizer benzodiazepine.

READ MORE: Several conditions placed on ‘Internet Black Widow’ ahead of release

He didn’t know Shepherd had three husbands before they met and that she served time in prison for manslaughter in the death of one of those spouses, or that the family of another husband suspected her of having had a hand in his death.

He said was lonely and she filled a void in his life.

WATCH: Extended interview with Alex Strategos
Click to play video: 'Internet Black Widow’s victim believes she could strike again'
Internet Black Widow’s victim believes she could strike again

Shephard pleaded guilty to stealing Strategos’ money in 2005 — three counts of grand theft from a person over 65 years or older, as well as other charges related to exploitation.

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Doctors found benzodiazepine in his blood, after he had been hospitalized several times and his son checked him into a care home. Police found a stash of pills in Strategos’ home. But police involved in the investigation couldn’t prove whether Shephard had anything to do with  his condition or the benzodiazepine in his blood.  In a 2012 interview with CBC’s the fifth estate, Shephard said:

“I can’t say that I didn’t personally give him benzodiazepines. If he had them in his system… we already knew, he knew and I knew, that our relationship was not going to continue.”

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But the police investigator who helped put her behind bars, has little doubt that’s what she was up to.

“I truly do think she was either trying to incapacitate him enough to perform the crimes that she was doing, or actually end up ultimately killing him which is what I think what would have happened to him,” Pinellas Park detective Sgt. Mark Lynch said in an interview.

Pattern of behaviour

Strategos said he doesn’t regret meeting Shephard and he doesn’t carry a grudge. He does, however, have a warning to any man who may cross her path: “Watch out.”

But if Shephard should happen to find love again, she’s going to have to tell the police about it first.

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It’s one of the nearly two dozen conditions Shephard will have to abide by after being released Friday from the Nova Institution for Women, after serving two years and nine months behind bars.

That’s because Shephard did find another unsuspecting victim after Strategos.

Following her release from a Florida prison in 2009, she was deported back to Canada and settled into a retirement complex near New Glasgow, N.S.

She married 75-year-old Fred Weeks in September 2012, after a whirlwind romance.

It was just a few days later, on their way home from a honeymoon to Newfoundland, when Weeks fell ill at a Cape Breton inn.

His new wife, according to an agreed statement of facts, had been slipping tranquilizers into his coffee. When police searched the room where they had been staying, they found notes with words like “lawyer” and “will.”

READ MORE: Friend wanted police to warn newlywed about ‘Internet Black Widow’

She was initially charged with the attempted murder of Weeks, but pleaded guilty in June 2013 to lesser charges of failure to provide the necessities of life and administering a noxious thing.

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WATCH: judge urged the public to be cautious “Black Widow” was handed her sentence.

Even though she has served her time — her third stint behind bars in relation to one of her husbands or lovers — authorities are skeptical she’ll be on her best behaviour.

It’s not just because of a rap sheet that dates back to the 1970s, but because of what counsellors and Parole Board of Canada officials saw during her time in prison.

According to the Parole Board, she hoarded six bottles of prescription eye drops, which the parole documents noted “was excessive and inappropriate use could have the potential to cause harm.” The parole documents also state she had a stash of antibiotic medication in her unit and was institutionally charged for improper storage.

Shephard also demonstrated that she tended to “fabricate stories to perhaps deflect blame” and to play the victim, according to the Parole Board. She also claimed a family member abused her as a child and that led to her actions later in life.

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Ex-boyfriend Strategos, on the other hand, thinks she is driven by a “love of money.”

READ MORE: Cape Breton inn owner recounts experience with ‘Internet Black Widow’

Just four months before her release this weekend, the Parole Board panel ruled Shephard remained “likely to commit an offence causing death or serious harm to another person” if she were to be released early.

Shephard, according to the Parole Board documents, didn’t believe she poses a risk to the public — just to her spouses.

But as far as Strategos is concerned: “She’s getting away with murder.”

Who were the other men who fell for the ‘Black Widow’?

Shephard was married three times before meeting Strategos, but it was her second husband, Gordon Stewart, who was her first victim.

She drugged him with benzodiazepine and ran him over on a remote road near the Halifax airport in 1991. She was not convicted of murder and instead served four years of a six year sentence for manslaughter.

They were only married for a few months. Documents from her parole hearings reveal Shephard gave Stewart drugs “to keep him quiet and especially to avoid sexual activity.” She claimed Stewart sexually assaulted her the day she killed him and that she backed over him in order to get away. She ran over him twice.

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Shephard became a widow again in 2002, with the death of a Florida man she married after meeting at a Christian retreat.

Robert Friedrich died of cardiac arrest after a series of fainting spells. Friedrich’s son suspected her of being involved in his death after reading about her manslaughter conviction online and that her previous husband, Stewart, had benzodiazpines in his blood when he died.

She denied that in the 2012 interview with CBC’s the fifth estate.

There was no way to know whether Shephard had slipped Friedrich drugs, as she is did with other men, because he was cremated immediately after his death.

With files from Global News reporters Natasha Pace, Ross Lord and Heide Pearson, NBC News reporter Mark Lynch and The Canadian Press.

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