Suspicion | The Billionaire Murders: The hunt for the killers of Honey and Barry Sherman: S2 The Billionaire Murders | E6 Family Matters

But I see my shriek now every week where I usually see him every two weeks.

I am clean and sober like, but I don't want to relapse.

Okay, wait till you taste that, Kevin, delicious.

Carrie Winter and I are in line at a hot table restaurant shortly after police announced

his cousin Barry and wife, Honey, were victims of a targeted double murder.

Carrie encourages me to try the lasagna and the steaming tray, and he's right, it's excellent.

He's the first of the extended Sherman family who has agreed to talk.

I want him to tell me about Barry the person, his connections to family, and the role his

immense wealth played in those relationships.

Carrie says he'll do his best, but he wants to make it clear he still thinks it's murder

suicide, and Sherman lawyer Brian Greenspan is part of the cover-up.

But this family's worth billions, and Barry actually snapped and killed Honey, but tried

to stage it like a suicide.

Because of their billions, and they have the access and the money to hire a guy like

Greenspan, they shouldn't have the right to rewrite history.

If Barry snapped and killed her, it's done, it's finished.

I'd picked an out-of-the-way table, but two guys sit down nearby and one does a double

take, recognizing Carrie from a television interview where he revealed he'd long fantasized

about cutting Barry's head off and rolling it down the Apatec sidewalk.

The guy gives Carrie a thumbs up.

After lunch, Carrie starts telling me about the good days he had with his cousin Barry,

before their relationship went off the rails.

I mean, there was fifteen years.

That man didn't just give me lots of money and banged for all my custom home business,

but he was a real mensch today, he was very kind to me.

Carrie's six feet tall, has a thick head of wavy dark hair, he's got big, powerful

hands from years of working construction.

I notice his face has bright red marks on it.

This is early in my investigation when one theory out there was that Carrie was the

killer.

I'm wondering if he's been in a struggle or a fight.

He says no, he's getting laser treatment to heal a skin condition.

Carrie starts talking about the old days with Barry.

His voice, well, he sounds like a radio DJ to me, energetic and expressive.

Here's a story.

Every year, you get these little photos of your children from school.

And he'd often ask me, bring your kids up to see me.

This is back in the early 90s.

And I always tell my kids, we're going to go and see cousin Barry, go in and give him

a big hug.

And he'd always take those pictures and put it on his desk in these frames right beside

his own shoulder.

Very few people could walk through the security doors of Apotex, literally walk through the

security doors, go down the hall, second door to the right, Jack's office, third door

was Barry's.

Honey could do that, and me.

Carrie and his three siblings, Tim, Jeff, and Dana, were the children of Lou Winter,

Barry's uncle.

Lou was a generic pioneer who gave Barry his start.

When Lou died, Barry purchased Lou's company, Empire Drugs, then sold it, and a couple

of years later, Barry founded Apotex.

Barry and his brothers were little kids when that happened.

Barry was in his 20s.

They reconnected when Carrie was an adult, and he would often just hang around the Apotex

office.

We would talk.

We talk of a love.

We talk about his unhappiness.

We talk about his unhappy marriage.

As Barry started his meteoric rise, he began funding enterprises started by Carrie, Jeff,

and Dana, and bought them houses, cottages, funded businesses, about $15 million in total.

Generous for sure.

But later, Carrie would see these as financial handcuffs.

Still, they were family.

But I'll never forget one time we were talking, and he looked at me and he says, you know

why I like you?

She didn't know why I like when you come up at sea.

He said, no.

I said, because you're always so euphoric, you make me laugh.

He said that.

I think you laugh as you make me laugh.

From the Toronto Star, I'm Kevin Donovan, and this is The Billionaire Murders, The Hunt

for the Killers of Honey and Barry Sherman.

Barry Sherman's mantra, how he liked to make money and give it away, didn't leave

a lot of time for family.

Other than a safari in Africa when the kids were very young, I haven't heard of too many

trips with honey and Barry.

But if someone was in trouble, Barry was there.

He liked to fix problems.

That pattern was laid down with his four young cousins.

I was on and off drugs the whole time I knew Barry.

He actually was instrumental in getting me off drugs, because Dan and my younger brother

also had a severe drug problem, and he had bankrolled at least one, if not two, treatment

centers, which was like 20 grand at the time.

Carrie's late brother, Dan, was, honey's friends have told me, charming, with a movie

star good looks.

He worked at a golf resort Barry owned, but was fired because he was sleeping with a female

golfers.

He also had a serious drug problem.

Barry funded a couple of rehab treatments, none successful.

Dana wound up dealing drugs and was charged by police in western Canada with a murder

for hire plot over unpaid drug debts.

Barry hopped on a plane and bailed him out, but just a few weeks later, Dana was dead

of a drug overdose.

For Carrie, a graduate of a good British college, drug addiction started with a form of cocaine

while he was backpacking in Peru.

Barry used to say, you're on drugs too, you're on drugs.

I'm not in minimize.

He said, I'm not so bad, I'm not so bad.

And then we made a deal.

He said, if you can't stay up drunk, I'm going to send you to a treatment center.

And I had a fear of treatment centers, because it was a revolving door for my brother Dan.

The idea of a treatment center didn't sit well with Carrie.

He proposed a different plan.

So I said, I'll tell you what, bro.

Let me work in the warehouse for three months.

He gave me a pair of boots and I pushed this little trolley cart up and down, just pulling

drugs off the shelves.

I was like an order picker.

And then I take it to this big table where they package it up.

It was like in the shipping to burger.

And I'll never forget the 90th day I walked in Barry's house, I dropped the boots on the

floor and he says, so you go into treatment.

I said, no, Barry, I'm coming up to 30 days clean.

His eyes opened up.

He says, say that again.

It was around this time that Carrie says Barry made a most unusual request.

One that Carrie would announce in shocking fashion to the world five weeks after Barry

and Honey's bodies were found.

There's Carrie in an interview recorded by the Daily Mail and played on city news in

Toronto.

In an interview with the British tabloid, the 56 year old claims his pharmaceutical tycoon

cousin had once asked him in the 90s to help hatch a plan to kill his wife, but eventually

decided not to go through with it.

I made a call knowing that my friend Louis could easily set it up because he was a quasi

gangster.

He knew a lot of bad people and he said, the body will go missing.

There's not going to be a bullet in the back of the head or a car exploding.

She's going to go missing.

And I said, Barry, Louis wants you to know that if we push this button, there's no turning

back.

I've changed my mind.

You know, you're right, taking out my wife, you know, it's not a good thing.

Now Carrie made the same claim to me and others in the media.

He told me he suggested that Barry simply divorce Honey.

But I know that he couldn't handle her getting half his money.

And I said to Barry, you've got so many billions hit.

All you do is give her a couple of billion and he says, you don't get it.

She's not getting the money.

I found his claim impossible to verify, though I did speak to an old friend of his who recalled

Carrie talking about the murder plot back in the 1990s.

But I've always thought there was a less sinister explanation that Carrie, when he was hanging

around with bad people, was talking big one day.

Barry called him on it.

I know Barry had a nerdish, almost scientific fascination with the rough side of life.

Yes.

He often asked about what it was like to take drugs.

He wanted to know what that was like.

I said, Barry, crack is a really bad drug.

So when you smoke it, you get this fucking rush because what's that rush like?

So I described it to him.

I said, but after you get really paranoid, it was wide.

I said, I know it's like the psychosis sets and you get them fucking weird and start looking

around and get all weird.

He goes, if that what happens to you when you do that?

I said, yeah.

He asked what it was like to shoot an arrow and I told him.

I said, I'd like doing that drug.

I put it to Carrie that maybe Barry was not serious about any of this drugs or murder.

Just curious.

And perhaps Barry said one day, hang on, Carrie, you say you have all these underworld drug

connections.

How bad are they?

Are they killers?

And you egged him on and Barry said, are you telling me you could get someone killed?

Like my wife?

In the restaurant, Carrie sat back and listened quietly to my theory.

His fork towing with a last bit of lasagna on his plate.

I think it might be rocket, but I know for sure he talked about it.

Carrie was adamant about one thing, Barry and honey did not get along.

He not only had to stain for her and that she would needle out, but then he had a terrible

temper, treating them like a piece of garbage and also the nagging from honey and making

derogatory comments how he could dress himself.

And one time she just says, did you believe this, Carrie?

Your cousin's going to come home tonight and I have to dress him because he couldn't

coordinate a pair of slacks and a jacket shirt and tie.

Like just bitter, cheap.

That there was turmoil between Barry and honey in years past comes up in the police interviews

with the four Sherman children.

These are statements taken at a time when police were still chasing the murder suicide

theory.

Cops were looking for an explanation as to why Barry would kill honey.

Lauren, the eldest, told a detective that growing up her parents were the swearing and

screaming type, but their arguments never got physical.

Daughter Alexandra called her parents' relationship difficult, but this improved over time and

Lauren said that in recent years her parents were getting along better and were seen holding

hands in public.

Carrie's knowledge of Barry and honey's relationship sounded historical, not current.

The guys beside us get up to go.

One of them insists on shaking Carrie's hand.

I can see Carrie likes the notoriety.

You have to understand, my hatred of Barry, my disdain for him was only because of his

portrayal and his lies.

The dispute began when his brother Jeffrey stumbled over an option agreement from Barry's

purchase of Empire Labs back in the 1960s.

If you recall, Lou Winter, Barry's uncle and the owner of Empire had died suddenly, leaving

behind a wife and four young children, Carrie, Jeffrey, Dana, and Tim.

Barry saw this as an opportunity to get into generic drugs.

He included the option to make his offer more attractive to the trust company looking after

affairs for the winter children.

Carrie and his siblings would later argue in court that this option entitled them to

a one-fifth share in Apotex, roughly $1 billion today.

Without Empire, they said, there'd be no Apotex.

In turn, Barry argued the option agreement was worthless, that it lapsed when Barry sold

Empire two years after he bought it.

It would only have been exercised if Barry still owned Lou's company when the four

kids reached 21.

I think that option is one of the earliest examples of Barry Sherman creating a legal

document to advance his own interests.

But just before the cousins took Barry to court, Carrie brought his kids to an Apotex

Christmas party for one last time.

I give you everything you want.

Why do you want to come after me?

The lawsuit got vicious on both sides.

Carrie said at one point he decided, forget the money.

He wanted something bigger.

His father lose name on a hospital and something else.

I said to Barry once, I don't want 20% of Apotex.

I don't want anything, Barry.

I just want you to tell me the truth.

Why do you keep lying to me?

Do you know how many years he lied to me about the option?

In the fall of 2017, Carrie and his siblings lost their fight.

The case over, Barry asked for $1 million in legal costs.

The judge knocked that down to $300,000.

This is another piece of information that feeds into my perfect storm theory, events

just before the murders.

But for now, let's think of the sad family tale that took 50 years to write.

I've talked to friends of Barry and they say the lawsuit both saddened and angered him.

Frank D'Angelo, who was on the receiving end of Barry's generosity for years, has this

take on why Barry fought his cousins so hard.

Dr. Sherman, this is the type of guy he is.

Barry will give you the sky, the sun, and the moon.

But if you fuck with Barry, you hit Barry with a fly swatter, he's going to hit you

with a fucking slide jabber.

We'll be right back.

It's funny, the Sherman wealth is so much a part of their story, but I don't think

Barry or Honey were ever comfortable with money or cared about how much they had.

I think Barry would have happily continued to fund his cousins if they'd not asked for,

in his opinion, too much.

This awkward relationship with finances influenced how the Shermans managed, or rather did not

manage, the expectations of their own children.

If you stop and think about it, growing up incredibly wealthy comes with its own set

of problems.

You see, Barry and Honey were millionaires by the time they were 40, billionaires in

their 50s, but they weren't spenders.

Their clothes were cheap.

Honey wore those same workout shorts for 20 years.

She bought belts on sale at Canadian Tire.

Barry had his uniform, khaki pants, white shirt, brown jacket, but he was happiest wearing

an Apodex lab coat.

And just look at their two aging vehicles.

Both had accidents the year they died.

Barry had a fender bender on Highway 401 heading home, and Honey hit a deer driving home from

a friend's cottage.

These cars were 15 and 10 years old, respectively, and both Barry and Honey got a mechanic to

do cheap repairs they boasted about to friends and family.

Maybe they were a little like investor and philanthropist Warren Buffett, worth over

$100 billion.

He still lives in a five-bedroom house in Omaha he bought in 1958 and drives around in

a seven-year-old Cadillac.

There was something in their brains that was just odd.

They didn't...

Well, in their way they did, I guess.

In everybody else's view, certainly in mine, they never enjoyed their material success.

That's Toronto real estate mogul Ed Sunshine.

He's also a philanthropist, a self-made man whose parents were survivors of Auschwitz.

Like Honey, Ed was born in a displaced person's camp.

He'd worked hard all his life and enjoys the fruits of his labors.

He never understood the Sherman approach.

Now they were going to build this big house in Forest Hill and maybe they were about to.

And they had a lovely house of old colony, quite beautiful.

But other than that, they, you know, in many ways I thought with Barry in particular it

was shtick, if you know what I mean.

It was like it had become his thing.

I mean, you know, and I'm not trying to brag or anything.

I happen to drive a Bentley, a convertible.

We also like, yeah, so he's selling my car, he shipped it down to Florida for the winter.

And we were in the same building in Florida.

So one day Barry and I are both downstairs and the valley, you can't park yourself.

So that way his my car comes driving up and looks at my car and his car comes driving

up and he actually didn't have his own car down there.

He had rent-threat car and, you know, he looks at my car.

The top was down already and he said, is that your car?

He said, you were at that car?

I said, no, it's my car from home.

I send it down here for the winter, you know, convertible as much as you said, oh, winter.

And he said, why don't you buy a car like that?

I said, because I really like it.

I said, it drives great.

I said, look at it.

It's beautiful.

It's a beautiful car.

And then we both looked at it and Barry, it literally was a chivette.

Senator Linda Frum, who worked with Honey on fundraising projects, recalls an interaction

with Barry that unsettles her to this day.

She'd invited them to her cottage for the weekend.

By the way, the Shermans didn't own a country place.

They thought it a waste of money.

Linda is the daughter of the late Barbara Frum, one of Canada's most famous broadcast

journalists, and she's married to a wealthy real estate developer.

Linda was helping her staff clear the table after dinner and Barry lingered in the dining

room.

And then he spoke about, you know, we had so much, we enjoy calling these beautiful things

and then people take down and then he did go further and say, you know, refer to my,

the two housekeepers who were helping in the kitchen and he said, you know, why should

we be served?

And they are doing serving and we're the ones, like, well, who decided that, who decided

that some people have to serve, some will get served.

He was struggling with this idea that the whole evening had been kind of a, you know,

sort of a cosmic injustice.

Then there's honey.

She didn't like Barry handing out millions to his cousins.

After all, she was frugal in her day-to-day life.

She'd lament that despite being a billionaire's wife, she didn't even have her own money.

Yes, she had a credit card, but Barry controlled the purse strings.

On her trips with the golf girls, they didn't charter a jet or even fly commercial.

Instead, they drove 15 hours in Honey's old Lexus and pooled money for gas, snacks, and

accommodations.

And when the three of them got to the modest condo Honey had arranged, the same thing happened

that always happened.

Honey, we did one, two, three, because we're going to get different, like, you know, we're

going to pull large numbers, right, for the rooms.

And one was absolutely enormous.

It had like a suite of its own.

Then there was like, there's like Papa Bear, Mama Bear, and you know, the baby bear.

So I pulled number one, which is the huge one.

Mata pulls number two, which is the Mama Bear size.

And Honey pulls the little one.

Any time I'd been with her, we only traveled to my husband's, we always get the better

room.

I says, honey, take the room.

She never did.

For Barry and Honey, money was for needs, not for wants.

That was Barry's credo.

Honey quoted it to her friends when they raised eyebrows over things like the used Timex

watch Barry bought at a yard sale.

When it came to flying, Apatex executives have told me that they would fly business class

to a business meeting and Barry would be an economy.

Ed Sunshine once asked Barry about his flying habits when they were getting on a plane.

I said, you know what, Barry?

I said, I don't know why you like to sit in the back.

And he looked at me and he said, if I could get a cheaper fare and I flew standing up,

I'd take that one.

I said, okay, Barry, good luck on finding that fare.

Once kids were added to the mix, that frugality got complicated.

Some got more, some got a lot less.

The line between needs and wants blurred.

Here's Jonathan during his eulogy, describing his father's very generous financial support.

You were also my business partner.

When I entered your office about five or six years ago with my good friend, Adam, we told

you about our plan to start a business together and you were so incredibly supportive and

excited.

We had the world's shortest shareholder agreement, which basically said anything, anytime.

As our third partner, you watched from the sidelines and gleamed with pride as we began

building our businesses.

You were always available to help us with funding and guidance.

Jonathan has told me his father gave him roughly $125 million to fund his self-storage business

and a cottage marina.

From my research, I think it was actually much more.

Lauren, the eldest, also received a lot of money from Barry.

Friends say they were told he gave her $100 million to invest in stocks and businesses.

Contrast that with the youngest Sherman child, Kaelin, who had for years been asking Barry

to buy her a $60,000 car, an Infinity QX60.

Days after her parents died, Kaelin ordered one from a dealership, telling family, that

is what he wanted me to do.

Alexandra, the third child, certainly received money, but nowhere near what Jonathan and

Lauren did.

It's clear Barry and Honey had different theories on wealth and how to bring up children, but

they were allied on one thing from day one.

They wanted kids.

Like many young couples, they test drove other kids before they had their own.

Barry and Honey babysat Joel Ulster's children, and Barry loved to roll around on the carpet

playing with the toddlers.

But having children proved a struggle for Honey.

She wanted kids desperately, but she had such a problem.

That's one of Honey's oldest friends, Bryna Steiner.

She and Honey went to teachers' college together, and she and her husband Fred were starting

a family the same time the Shermans wanted to.

Honey had a series of miscarriages, but gave birth to Lauren in 1975.

She's the only one of the four who have both Barry and Honey as a biological parent.

After Lauren was born, the Shermans turned to surrogacy, which was relatively new at

the time and not common in Canada.

Using Barry's sperm and, in each case, a different surrogate mother in the U.S., using

an egg from that mother, came three more Sherman children, Jonathan in 1983, Alexandra in 1986,

and Kaelin in 1990.

Barry flew the mothers to Canada so the children would have Canadian citizenship.

As the Sherman family grew, the daily duties of raising the children went to Honey.

But friends say that as the children grew older, it was Barry they would call for help.

Here's Barry's friend, Joel Ulster.

You know, when his kids were older, and of course he wasn't home a lot, but he was always

available.

To say the relationship between Honey and the children was strained is a gross understatement.

Mary, Honey's sister, told me that Honey referred to her children as the Nazis, a horrible

descriptor, particularly coming from someone with Honey's upbringing.

She told her friends that the children controlled her.

In the family pecking order, she was at the bottom.

And perhaps as a reaction, Honey was tough on the kids.

Here's one example.

After Lauren's seventh birthday party, Honey gathered up all the presents and put them

in a room, not letting her open them for several weeks.

Honey's friends think she was trying to stop their firstborn from being spoiled.

The children grew up to see Barry as a softer touch.

Because he was easier and more, I guess empathetic, he was less, you know, he had strong ideas

of what they should do and stuff, but it didn't matter that they didn't do it.

The Sherman home was not a happy one.

Tensions over money, tensions over lifestyle.

Honey was not accepting of Jonathan when he came out as gay, and neither Jonathan's

long-term boyfriend Andrew, or his eventual husband Fred, felt comfortable around Honey.

There were also tensions over what they were doing with their lives.

Barry wanted his kids to work at Apodex with an eye to one of them rising up through management.

None were interested.

This turmoil led to years of therapy.

One of my sources shared emails between Barry, Lauren, and Jonathan.

These were also shared with the police.

They're upsetting to read, and they give a very different perspective from those of

Barry's friends, who paint a picture of Barry doing his best to help his kids.

Here's one from Lauren in 2008.

She was 33 at the time, living in Western Canada.

You say that you love us kids, but your actions show that you don't.

You have always hated Kaelin, and it's pretty obvious that you hate John too now.

These folks are my siblings, my team.

As such, I feel hate towards anyone who hates on them.

I also despise the way that you feel about and treat me.

Our relationship is not possible under the current emotional circumstances.

Let me know if and when those circumstances change.

In the email chain, Lauren is writing in defense of Jonathan, who was upset that their father

was continuing to fund Frank D'Angelo's businesses.

That's a sore point in the family, which I'll get into later.

Lauren, who runs a yoga and therapy studio, and who herself received millions from Barry,

talks about the toxic effect of money.

You have worked very hard to make money for your whole life.

At this point, making more money won't help you at all.

In fact, I think that having produced too much money is a big part of your hour problem.

Perhaps it's time to slow down at work and start spending time nurturing loving relationships

with your kids.

On your deathbed, I doubt that you'll be thinking, gosh, I wish I made another billion

dollars.

I bet you'll be thinking, gosh, I wish I loved my kids better.

I really wasted my life.

I am so sorry.

Barry responds, Lauren, your emails are frightening.

They are increasingly accusatory and extreme.

I know without doubt that I am a loving father to all four of my children.

And there is nothing that I would not do to try to ensure your happiness.

Yet you continuously paint me as a monster.

For years, I have tried to speak to the four Sherman children.

It's actually quite normal for the family members of murder victims to speak to journalists,

especially when a crime is unsolved.

Family wants to keep the story alive in the press with hopes that it will urge police

on, not so with the Shermans.

In my almost four decades of reporting, I've never found a family veil more difficult to

lift.

Neither Lauren or Kaelin have ever agreed to be interviewed.

But in time, I was able to speak to their sister, Alexandra.

She's a nurse by training, has worked in Northern Canada, helping people with low income.

And of all the children, she's the least interested in wealth.

She has spoken of how proud she was of their father.

Like, I loved him.

I respected him.

And, you know, he did a lot of wonderful things for the world and for Apatak.

In my interviews, Alexandra doesn't speak much about her dad as a father and never speaks

about honey.

But it's clear she looked up to her dad as a business leader.

My dad had values and morality and principles and respect.

And Apatak's employees were treated well.

It's like a family, you know, like if you saw an employee struggling, he would help

no matter what the situation, and Apatak said, you know, 11,000 plus employees.

There's something else about Alexandra.

A shocking turn in the already difficult family dynamics.

Roughly one year after Barry and Honey were murdered, Alexandra began developing a belief

that her brother Jonathan was somehow involved.

It came after a visit to his cottage in Eastern Ontario.

I heard the story from numerous sources and also that she went to police with her suspicions.

Naturally, I wanted to ask Jonathan about this.

Leading up to the publication of my book and a series of stories on the case in the Toronto

Star, I asked Jonathan by email if he had anything to do with the murders.

In a letter he wrote back to me copying the Toronto Homicide Squad, he referred to the

allegations that he was involved as insane accusations.

He suggested that I was hearing these allegations from people that he considered persons of

interest in the murders of his parents.

And then in late 2020, I heard a new allegation.

You'll recall Jonathan's comments at the funeral of his father's strong financial support

for his businesses.

My sources were telling me that in the weeks leading up to the murders, Barry was cutting

Jonathan off.

Using an email address Jonathan had set up to communicate with me, I reached out.

I invited him to provide context and explanation to finally give me an interview.

On December 15, exactly three years to the day his parents' bodies were discovered, Jonathan

emailed me, come to my home north of Toronto, he said, and come alone.

Next time on The Billionaire Murders.

I could tell you things that would make you go, oh shit, there is information out there

that would make you go, holy fucking shit, it's unbelievable.

The Billionaire Murders, the hunt for the killers of Honey and Barry Sherman, is written

and narrated by me, Kevin Donovan.

It was produced by Sean Pattenden, Raju Mudar, Alexis Green and JP Fozo.

Additional production from Brian Bradley and Crawford Blair.

Pattenden Music was created by Sean Pattenden.

Look out for my book, The Billionaire Murders, and coming later this year, The Craved Documentary

by the same name.

Machine-generated transcript that may contain inaccuracies.