The No Good, Terribly Kind, Wonderful Lives and Tragic Deaths of Barry and Honey Sherman: Chapter Four: The Winters are Coming

Uncover from CBC Podcasts brings you award-winning investigations year-round.

Infiltrate an international network of neo-nazi extremists.

Here, granted, with racist language.

Discover the true story of the CIA's attempts at mind control.

Their objective was to wipe my memory.

Or dig into a Crypto King's mysterious death and a quarter billion dollars missing.

There are deep oddities in this case.

With episodes weekly, Uncover is your home for in-depth reporting and exceptional storytelling.

Find Uncover wherever you get your podcasts.

Alliance Gate Sound and CBC Podcast Production

Do you watch Succession, the HBO hit series about a ruthless billionaire family, the Roy's,

fighting over who will take over their father's media empire?

None of the kids get along.

They're all competing for their dad's favor.

And he has no problem setting one kid up against the other.

Sometimes to help the business, but sometimes it seems just for sport.

It's sick and dark and really addictive.

Succession's wild popularity is partly because we're fascinated by the rich.

The dysfunctional elite.

The warring relatives fighting over huge fortunes.

Which helps explain why the deaths of Honey and Barry Sherman

have captured so much of the public's attention.

Just like the fictional Roy's, the Sherman's were billionaires.

And just like the Roy's, the Sherman's were involved in a cutthroat industry filled with intrigue.

What we haven't told you about yet is the family in-fighting.

And just like Succession, the story behind it all, it's a doozy.

Welcome to the no good, terribly kind,

wonderful lives and tragic deaths of Barry and Honey Sherman.

I'm your host, Kathleen Goldhardt.

And this is Chapter 4, The Winters Are Coming.

Like most family dramas, to understand them, you have to go back to the very beginning.

Remember when I told you about Barry's uncle, Lou Winter?

Lou was a pioneer of the generic drug industry, who hired Barry when he was still in university.

Introducing him to the world of patents and fighting big pharma.

I met Barry and then Lou died very suddenly.

That's Murray Rubinigan, a longtime friend of Barry's.

I spoke to him and his wife, Rhoda.

We had gone out for dinner. Do you remember that with Lou and his wife?

I would say a month before she died, we didn't know she was sick.

I believe she had cancer.

But I don't remember the cause of death for him.

But it was, we couldn't get over it. We had just seen them.

And it looked fine.

And they had young kids.

Yeah. I think they had five kids.

I'm not sure.

Maybe it's only three.

Actually, it was four.

All boys, all under the age of seven.

Do you know what happened to the kids?

They were adopted by another family. I can't remember the name.

I wish I remembered. The problem with me is memory now at this age.

The tragedy was decades ago and details understandably fade.

In 1965, Lou and his wife, Beverly, died just weeks apart.

Lou unexpectedly of a brain aneurysm.

And then just 17 days later, Beverly died from leukemia.

She was 31.

Their four young children, Dana, Jeffrey, Kerry and Tim, were suddenly orphaned.

A Jewish family in the community adopted the boys.

And as they grew up, the Winter Brothers had a really tough go of it.

It's a really sad story.

They struggled with drugs and lost touch with Barry completely.

That's Canadian journalist Matthew Campbell, the Bloomberg reporter.

Really having a terribly hard time and with no idea that they were related to someone who was so

wealthy. So when they did reconnect, which was in the late 80s, Barry, as he often was,

was extremely generous. He helped them with everything he could.

He would bankroll business ideas, help them pay for things like drug rehab,

really trying to turn their lives around.

And we actually do know how Barry felt about reconnecting with his younger cousins.

When they came to see me, they were in trouble. They were drug addicts.

Kerry was a drug addict. Dana was a drug addict.

This audio of Barry was obtained by CBC News, the Fifth Estate.

They did a documentary about a bitter lawsuit between Barry and the Winter Brothers.

This clip is from a 2017 deposition.

Like they did everything I could to help them, even to start their own businesses.

With Kerry here, I said to him, as to what is it you want to do, Kerry?

You got to make something out of yourself. He said he wanted to do renovations.

I said, fine, I'll finance a renovations business for you.

Get some training, buy a property, work on it.

And Kerry, who was only four years old when his parents died, took him up on that offer.

I had this billionaire who was about to give me anything I wanted.

He said, I want to help you make a life for yourself.

It slowly started off with a couple hundred thousand, but within three, four, five years,

it was houses and cottages and sports cars. And literally,

it steamrolled and snowballed into about 15 years later, being about five, six, seven million.

In his deposition, Barry said he believed he did right by the Winter Brothers,

that he did everything he could to help them.

And Kerry concedes that Barry did totally support his lifestyle and his business.

Barry also backed his brother, Dana's jewelry business,

and helped his other brother, Jeff, with his travel company.

So I'm simply saying that I'm a person who does like to help friends and relatives and

other people to the extent that I reasonably can.

The rest of the audio from Barry's deposition is a bit hard to make out.

What he goes on to say is that, quote, I think I'm a generous person.

Who else would spend 15 million dollars trying to help his cousins establish careers for themselves?

And for a while, things were getting better for both men.

I mean, they had had a very close relationship, Kerry and Barry,

and they would talk. They enjoyed being in each other's company.

They spent a lot of time together.

But then things began to unravel.

I don't think anyone else in his right mind would have done for them what I did.

I spent about 15 million dollars trying to help the three of them all down the drain,

trying year after year after year to help them make better lives for themselves.

This is the actor Saul Rubineck again, reading from Barry Sherman's deposition.

It outlines how Barry did help the Winter Brothers,

how he took Dana under his wing, getting him a job at Apotex,

hoping it might kickstart a career.

Then I moved him up to Deerhurst Resort.

He worked there for a long time.

Then he was dealing in drugs there.

Then he moved him out to B.C. and he was dealing in drugs there.

And then he got involved in a murder case.

Remember I told you this story was a doozy?

In 1995, Dana, who had been dealing drugs,

was charged with conspiracy to commit murder of a man who Dana believed

had ratted him out to the police.

Barry was asked about this during a deposition.

Were you involved in that murder case, sir?

The lawyer is being read by an actor here.

I was involved to the extent of going out, flying out.

You didn't help him commit murder, did you?

You heard that right.

The lawyer just asked Barry if he helped Dana commit a murder.

No, no, no.

Let's look at that.

I did fly out to B.C. and get him out on bail.

And when he was out on bail,

you flew out yourself.

Yes, I put a $100,000 bond to get him out on bail.

Hired the criminal lawyer in British Columbia, got him out on bail.

And he was dead a couple of weeks later from an overdose.

Dana died of an overdose while he was out on bail.

He was just 33.

The relationship between the remaining Winter Brothers and Barry

stayed strong for a few more years.

But that all changed when Jeffrey Winter

discovered something about the sale of Empire Labs,

his late father's business.

Barry bought Empire Labs when lose children were still very young.

But Barry had agreed to include a clause

that stipulated when lose children came of age,

they would have the option of buying 20% of the company.

Six years after Barry bought Empire Labs,

he sold it for $2 million.

And he used that money to help start Apotex,

a business that would eventually be worth billions of dollars.

When the Winter Brothers learned about the clause,

they felt cheated out of a fortune.

They wanted their 20% and since Empire Labs was gone,

they believed they had a right to a portion of Apotex,

a claim that would have been worth about a billion dollars at the time.

And that was the basis of the lawsuit they launched

against their cousin Barry,

the one that really ripped the families apart.

Sure, Barry used the $2 million he got from selling Empire Labs

to help start Apotex,

but he didn't believe that the Winter Brothers

had any claim to his new business.

And according to Barry,

Carrie Winter was furious.

One day,

Carrie, I can't remember when,

Carrie phoned me up and he was absolutely wild.

And he told me that he figured out that I was helping them

because I didn't want them to find out

that I was involved in some conspiracy

to deprive them of their inheritance in the 1960s.

Carrie Winter began to believe

that Barry's years of generosity

was really part of a convoluted conspiracy.

That Barry was placating them

so they would never go after the 20% of Apotex

that the Brothers believed they would do.

Of course, I told Carrie,

the whole thing was ridiculous.

The implication is that I anticipated

that they were going to sue me

and I lent them money and lost millions of dollars.

That somehow that would give me control over them,

that they wouldn't bring an action.

Which if preposterous makes no sense,

I had no idea they were going to bring an action

in any event.

How does it stop them from bringing an action?

In typical Barry fashion,

after the Winters sued him, he sued them back.

And he didn't just ask to have the millions of dollars

he lent his cousins over the years repaid,

he wanted his legal fees covered too.

So for 14 years, it was okay to help the Winter children,

but now that they have sued you, it is no longer okay.

That's an actor representing another lawyer for Carrie Winter,

Ely Scarlett.

Incidentally, Ely is also Carrie's ex-wife.

Well, let's assume there is a connection there.

So what?

Are you suggesting I have an obligation

to support people who are suing me?

And you've always loaned them money.

Lent. Loaned is not a...

Lent them money.

Lent them money, yes.

Allow me one digression.

At the Sherman's funeral,

more than one person spoke about Barry's tendency

to correct people's grammar.

They made it sound endearing.

It's not.

It's condescending.

If you're telling me I was foolish

and should have cut him off much earlier,

that's probably true with hindsight.

I'm not telling you anything.

I'm asking you questions.

That's all I'm asking right now, Dr. Sherman.

I'm not telling you anything.

I think your tone of voice is saying certain things.

We all know that this was not Barry's first legal battle.

But usually, Barry employed the legal system for business.

Very impersonal fights.

Clearly, this one was personal.

This is what Carrie Winter alleges Barry said to him.

He said,

You know, not too many people have a cousin, Barry.

Do you know what I mean by that, Carrie?

Do you hear what I'm saying?

And he leaned forward and he looked at me and he says,

You won't beat me.

Do you understand that?

Do you know who I am?

And Barry was right.

They didn't beat him.

On September 15th, 2017,

more than 10 years after the court battle began,

and three months before the Sherman's were found dead,

the winter's case was dismissed.

The judge who threw it out called their claim

wishful thinking and beyond fanciful.

The court decided that original agreement

applied only to Lou Winter's former company, Empire Labs,

which Barry Sherman had sold off before he formed Apatex.

Even worse, his cousin Barry was calling in

all the IOU's Carrie Winter had signed

for the cash advances he'd been given over all those years.

So Carrie Winter now owed Barry Sherman $8 million.

Carrie had to sell his house and a cottage to pay up.

It should have ended there, right?

I mean, the case was dismissed.

The Sherman's were dead.

But no, a day after the funeral,

lawyers representing Barry filed an appeal.

They wanted an additional $900,000 in legal fees.

It's as though Barry Sherman was litigating from the grave.

So I was heartbroken. I was betrayed.

And so a month after the Sherman's were found dead,

while the theory was still murder-suicide,

Carrie Winter agreed to do this interview

with the Fifth Estate on CBC.

It proved to be incredibly controversial.

He wasn't this loving, kind person giving money away,

pillar of the Jewish community.

He cared about one thing, money, making lots of it,

and not caring who he destroyed, who he stepped on,

or who he fucked over, like me and my brothers.

That's Carrie Winter,

clearly emotional and full of spite for Barry Sherman.

This whole documentary is wild.

Remember, this aired just seven weeks after their death.

And here was Carrie on national television,

saying his cousin was essentially an asshole.

But that's not all.

The CBC did more than one interview with Carrie,

and in the next clip,

they talked to him inside a busy Toronto coffee shop.

And that's where he said this.

Not only does he tell the CBC

that he's fantasized about killing Barry,

Carrie also tells them exactly how he'd do it.

The way I was going to do it wouldn't have been belts.

It was going to be in the Apatex parking lot.

That was my vision, always,

that he'd come out of the building in Apatex

and I'd be hiding behind a car.

And I just decapitated.

I wanted to roll his head down the parking lot

and I just sit there waiting for the police.

Naturally, Carrie was questioned by police.

I mean, I had opportunity, I had motive.

I can see why the police might say this guy's also a fucking nut.

Remember, the exact time of the Sherman's death is unknown.

But it's believed that it was some time

between the evening of Wednesday, December 13th,

and Thursday, December 14th.

Their bodies were found on a Friday.

Carrie says he told the cops exactly where he was.

No alibi. Wednesday night I went to my cocaine anonymous meeting.

I came home, as I usually do, watch some Netflix,

eat some Doritos, fall asleep.

Thursday night, same thing, went to work.

Very easily for me to have left work at any time

because I'm not on the clock.

I'm a site supervisor.

I can get in my car.

I can take a three-hour break during the day.

I could easily have driven over to Colony and done the deed.

I admit to that, but I didn't.

I didn't.

And that's why I'm not nervous.

And as I've told you, all these years later,

the police have not arrested anyone.

And Carrie told the CBC

that the police have told him that he wasn't a suspect.

Did you kill Honey and Barry Sherman?

Absolutely not.

I had nothing to do with it.

Toronto police have asked him to come in for an interview.

Winter says they told him he is not a suspect

and that there is no evidence he is.

The CBC interview didn't stop with Carrie professing his innocence

and saying that he had been cleared by police.

He also talked about the moment that he got the call to tell him

that Barry and Honey Sherman's bodies had been found.

And I just calmly said to him on the phone,

I don't believe it.

He finally did it.

I said, he killed her.

And to this day, in this moment in front of you,

I've never shed a tear about that and I've never questioned it.

Carrie's talking about Barry here,

implying that his cousin killed his wife and then killed himself.

And that was the original police theory.

But we know that didn't sit well with the Sherman family.

And six weeks later, Toronto police changed their theory

and started calling it a double killing.

So why was Carrie so certain it was murder, suicide?

Because he says that Barry had told him he wanted Honey dead

years before.

Carrie claimed that Barry, back when they were still getting along,

quietly asked him for a favour.

He asked Carrie to find someone to kill Honey.

He just wanted her gone.

He wanted her gone.

Carrie said that he even went so far as to hire someone to do the job.

But then Barry backed out at the last minute.

I called him and said, you know, there's no turning back, Barry.

If I push the button and he said, no, don't do it.

And that's when I said, then don't bring it up again.

And he never did.

Carrie's claim, of course, was huge, but he had no way to back it up.

Barry was dead.

And if there was a hitman out there, he wasn't talking.

So the fifth estate asked Carrie to sit for a lie detector test.

And he failed it.

The whole episode is really uncomfortable to watch.

Carrie is clearly angry and distraught.

And the audience is left unsure what to take away from any of his claims.

We wanted to ask him as well, but up to this point,

he hasn't replied to our requests.

This battle, it was between Carrie, his brothers, and their cousin, Barry.

But we've been told that when the winters launched their lawsuit,

Honey turned her back on them entirely.

Carrie especially became persona non grata.

And whatever affection or care she might have had for him, it was gone.

It must have been hard for Carrie to lose the connection he had with Barry and Honey.

He had lost his parents at such a young age.

And the Shermans had stepped in, offering a semblance of family that he must have been missing.

She'd looked after my children like her own.

That's Mary Shekman, Honey's sister, talking at her funeral.

Honey may have cut off ties with Barry's side of the family,

but she remained very close with her sister's kids.

If I wasn't there, one time I wasn't there, my kids got sick.

She's the one that would go over.

She'd get soup, she'd get things, she would constantly call.

She was the most loving, caring person.

Honey didn't just support her sister's family emotionally.

She supported them financially.

But when Honey and Barry died,

another family was about to be ripped apart over their money.

We're just looking to get a copy of a court file that is active.

Is this, do we have to fill anything out?

Yes. What year is the file?

What year? It's 2021.

Producer Michelle Shepard and I are at a courthouse in Toronto

where civil cases are filed.

So we wrote the number statement of claim defense in my email.

That's all you need.

Yes, yes. Then I can email them to you.

Okay, thanks.

Thank you. Thanks for your time.

I appreciate it.

Bye.

Bye.

As soon as we walk off the elevator and back on the street,

an email from the clerk arrives.

I can't believe that they sent that to us so quickly.

We're just out of the building.

Yeah, that was very fast.

Honestly, court records never come that quickly.

We sit on the steps of a nearby building and open up the file.

Two files, actually, a statement of claim and one of defense.

It was filed in June 2021 and it's ugly,

involving Mary, her husband, Alan and their son, Noah.

Honey, Sherman created the trust as a tax effective means

for Mary to accumulate wealth.

In January 2000, Honey set up a fund for her sister's kids.

They called it the Schechtman Children Family Trust.

Mary and Honey were incredibly close as sisters and best friends throughout Honey's life.

Honey had very contributed fund to the trust.

However, Mary and Alan were responsible for managing the trust

and utilizing its assets to build wealth.

The trust is made up of numerous properties in Toronto worth millions of dollars.

Noah argues that his mother and father hurt him

when they transferred 15 of the properties

to either themselves or their two other children.

Noah seems to have gotten nothing.

Honey intended that Mary could take advantage of the capital

that Honey and Mary could contribute, grow the trust assets

and in turn benefit as Mary saw fit from the value so great.

Honey intended that Mary and Alan would have the final and absolute say

of how the wealth Mary accumulated was distributed.

Mary, her husband, Alan and Noah's siblings

countered that they hadn't breached any agreement.

In other words, the defense argues that Honey didn't specify

how her sister could distribute the money.

The tensions between Noah and his mother are laid out in the court documents.

In them, Noah states that his relationship with the trustees,

particularly his mother Mary, has been fractious for many years

and that, quote, Mary has displayed an open animus and hostility towards Noah.

The Shekman family uses the same words to describe Noah, that, quote,

Noah has displayed an open animus and hostility towards Mary.

So they're seeking 40 million.

Wow. Breach of fiduciary duty and breach of trust.

Once again, the Sherman's money is tearing families apart.

Just like it does in the TV show Succession.

That much money is not good for any family.

Relationships between parents and their grown children are complicated enough.

Add in millions and millions of dollars, and you can see how distrust and animosity

can take over and tear any family apart.

It certainly makes for good TV.

But in real life, it's tragic.

I wonder who the Sherman's and their families would have been

if Barry had not been so successful.

So much of this podcast has been about Barry.

But what about honey?

Honey seems to be a secondary character whenever this story is covered.

But her effect on her family, her friends, the city, and the country is huge.

So that's where we're going next time on the no good, terribly kind,

wonderful lives and tragic deaths of Barry and Honey Sherman.

There is a weird and awful irony that her violent death harkens back to the trauma

that her own family experienced.

I remember when I first heard the news, that's the first thing I think about is

that's not right.

The whole thing is just not right.

This episode was written and produced by me, Kathleen Goltar,

Michelle Shepard, and Lisa Gabriel.

It was executive produced by Charlie Webster, along with Lisa Gabriel and myself.

Andrea Varsani is our associate producer.

Our technician is Laura Antonelli, sound design and mixing by Reza Daya.

The role of Barry Sherman is played by Saul Rubenek.

Stuart Cox is the executive producer for Antica.

Special thanks to Isabella Kempf.

This is Alliance Gate Sound Co-production with CBC Podcasts.

Alliance Gate Sound engineered by Pilgrim Media Group

in collaboration with Antica Productions, exclusively for CBC.

Machine-generated transcript that may contain inaccuracies.