Drug smuggler: A Hamilton woman’s journey from St. Lucia to prison

She’s smiling, talking, shifting back and forth to get comfortable.

Maybe she’ll order a sandwich.

Normally, she’d be drunk by now, but it was early this morning when they checked out of the resort — too early to pound back 10 drinks as usual — and she wants to be sober to face what’s about to happen.

The tension is unbearable.

This flight from St. Lucia feels so long — even worse than when she travelled to Indonesia a few years ago for a eight-week internship after she graduated university.

All she wants to do is get off the aircraft in Toronto and get this over with.

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• Dec 31, 1969

• Dec 31, 1969

THE JIG IS UP

It’s 9:40 p.m. on July 4, 2015.

She feels so obvious.

Her eyes dart back and forth as she shuffles through Pearson airport and pulls down her already shin-length dress.

The long, blue-and-white-patterned garment she’s wearing is a far cry from the Vans brand skateboarding tank-top and shorts she’d normally wear back from a tropical destination.

But this outfit isn’t a fashion choice.

Slender with purple and blonde hair, she and her travel partner arrive at the secondary screening area together. They are separated for examination.

She wasn’t given much direction on what to do at this point, except to say she’s his girlfriend.

The questions from the border services officer begin.

Has she done drugs before? (Yes.)

When was the last time? (A couple weeks ago in Vegas.)

Does she have any drugs in her bag? (No.)

At some point, the officer notices something under her clothing.

Is there anything concealed on your body, he asks her.

She doesn’t respond and looks away. Her face turns white.

The officer asks her to look at him and repeats the question.

AN ORDINARY CHILDHOOD

Born in Hamilton on Nov. 3, 1988, Emily Ann O’Brien was brought up on a tree-lined street in Westdale in a three-storey brick home she shared with her father, mother and two sisters.

Raised in a middle-class Catholic family, she grew up a tomboy and an introvert at heart. While she had a couple of girl friends, she preferred to spend time at the library reading books and borrowing CDs than with other people. She was into musical theatre and sports, mainly basketball. She spent summers at camp and her family’s cottage.

High school brought out a rebellious side of O’Brien.

She remembers being caught with the drug ecstasy and telling her mom she sold it. She’d run away for nights and get into screaming matches with her parents.

She started to drink, which made her more social and took away some inhibitions.

“I liked that feeling,” she recalls. “It’s not something I had in elementary school.”

She tried cocaine and liked it.

After she got in with the wrong crowd while at St. Mary Catholic Secondary School in Hamilton’s west end, O’Brien transferred to Westdale Secondary School in Grade 11.

That’s where I first met her. We were in the same grade, but neither of us can recall a time we’ve seen each other since I graduated high school in 2006.

After she graduated, O’Brien took a gap year before she headed to the University of Guelph to study international development.

For birthdays and other holidays, she longed for experiences instead of things, and so she received a month-long volunteer trip to Costa Rica where she spent two weeks in the rainforest and another two weeks saving sea turtles.

It was her first solo venture.

After that, she spent a few summers in Western Canada. While at university, she led a Habitat for Humanity trip to Texas, and when she graduated, she went to Indonesia on an internship with the Ministry of Foreign Affairs.

When she returned, O’Brien moved back with her parents before heading to Toronto to study international business at George Brown College in January 2014. She and a friend from university got a place together in Liberty Village — a trendy neighbourhood for young professionals.

It became her Toronto party summer. While she already drank and had used cocaine, her use of both became excessive — exacerbated by family issues with which she struggled to cope.

Their apartment was littered with a life-sized Justin Bieber cutout, paintings and crafts created while on drugs.

While she partied a lot, she also worked to build her business, a small social-media venture.

She would work hard during the day and then go out at night.

She got involved with a few start-up communities and made sure to attend local networking events.

But her personal and professional business mentor from the United States started to call her out for not developing the company as fast as he thought she should.

O’Brien justified her behaviour — she wasn’t drunk all the time — and she had been focused on building her reputation for social media.

That’s how she met her co-accused.

She reached out to him on social media to offer him a free trial of the app she had been working on.

He hired her to do social media for his company.

At the same time, the two started to develop a casual romantic relationship.

He bought her a watch, dessert wine, a sound system. He would babysit her dog. And in May 2015, he helped her move into a place on her own.

In hindsight, she says she should have known something was up when the $500 cheque he paid her with bounced.

And then there was the $10,000 she gave him for a car she never received months before they left on their trip. Something kept going wrong with it, but he promised his friend would pick them up from the airport in it, ready to go, when they returned.

She felt he charmed her and got her to trust him as she spiralled out of control with drug and alcohol use.

He seemed to know the right questions to ask given the vulnerable state she was in.

Afterwards, she felt so pathetic and realized how ignorant she had been.

“Emotions take over,” she said in a recent interview. “Every single human runs on emotions and every single human on this planet wants to be loved and feel like they’re good enough for that person.”

Despite everything she’s been through, O’Brien doesn’t want to name her co-accused. She wants to separate herself from him and doesn’t want to draw attention to him and his family. As far as she knows, his case is still before the courts.

TELLING THE TRUTH

O’Brien sits in a holding cell at the airport, ignorant to the severity of the crime she committed.

Perhaps surprisingly, she’s relieved. She knows she did the right thing when she told the truth — a welcome break from the panic she’s felt for the last three days since she realized she wasn’t coming back to Canada without drugs.

She can’t remember how long she stayed in the cell, but because it was a weekend, O’Brien was eventually moved to Vanier Centre for Women — a Milton jail — where she remained until she appeared in court the following Monday for a bail hearing.

Her dad hired a criminal lawyer.

In a Brampton courthouse, O’Brien’s parents put up $50,000 bail, using part of their mortgage as collateral. She was placed under house arrest and lived at her mother’s home in Westdale. Her mom, dad and two aunts were her sureties.

She still didn’t believe she was in that much trouble. She had a flight booked to Boston the next month, which she thought she could keep if she pushed the trip back.

She was shocked she had been arrested.

“I was so naive. I had no idea,” she said. “I was never a big-time criminal, so I had no idea how the justice system worked.”

At the same time, O’Brien was “walking on eggshells” around her family. They were hurt and confused and didn’t feel like she was taking the situation seriously.

Had she been living some sort of double life? Had her past travels to Asia, Argentina, Peru, Turks and Caicos Islands and Colombia been motivated by drugs instead of the volunteer work and exploration she’d said?

Travelling wasn’t new for O’Brien. She started to spend her own money on it when she was 18 and it remained a large part of her life. She wonders now if her trips combined with her substance use made her a target for recruitment.

THE PLAN IS HATCHED

It was a summer day when he started to send her cryptic text messages, saying he had something he wanted to ask her. He came over. She had been drinking.

He told her he wanted to take her on a trip. He would be bringing drugs back to the country. He wanted her to smuggle some, too.

He tried to assure her nothing would go wrong, and if it did, he would take the fall.

She believed him. The two had a close relationship, and she took him at face value. She liked to believe the best of people.

So later that night, when he started to text her again about the trip, she agreed to go.

“Part of me is like I know this isn’t a good idea,” O’Brien said.

But a week later, they were on a plane.

She saw it as a vacation, determined she would not be coerced into bringing anything back.

She knew what he was doing was wrong, but she also felt people often cover up for others when they’re in a relationship.

O’Brien arrived at the airport thinking they were heading to Puerto Rico for a week.

The tickets purchased by her co-accused said something else.

She said she was told the destination had been St. Lucia all along, and that her drinking and drug use left her confused.

She blamed herself. She still doesn’t know the truth.

THE UNCOMFORTABLE HOLIDAY

They flew into St. Lucia on a late June weekend. The all-inclusive resort provided plenty of opportunity to mask reality with alcohol and pretend everything was fine.

She partied throughout the week.

But on Wednesday, things changed.

She was told she had to get in a car and go to “work.”

“There was no decision for me,” she said.

Her disposition flip-flopped from whiny to stoic, and she demanded her co-accused get her drugs so she could feel braver.

That day, a car came to pick them up from the resort. It was driven by a quiet, local man who didn’t say much.

O’Brien stared out the window blankly, trying to avoid taking in anything around her.

“I just knew I was in it so I kind of ignored my surroundings,” she said.

Eventually, they arrived at a house on a hill. There were people there. It was the middle of the afternoon.

They spent an hour having their measurements taken for custom “granny panties” bricks of cocaine could be stitched into.

“I knew at this point I wasn’t going to call the police,” O’Brien said.

People at the house took her to the mall to pick out a “drug smuggling” dress. A woman who went with her took her passport and told her to pretend they were shopping. She pointed out the type of dress O’Brien should choose.

The woman kept the dress and they headed out to the parking lot.

Back at the resort, O’Brien tried to act normal. She was “obliterated,” lying on the beach drunk and taking pictures to send to her family.

But she also had work to do for her business.

She said her co-accused started to act paranoid and give her “attitude” when she was working up at the bar. He was at the pool and wanted to know where she was.

O’Brien started to be mean to him and ignore him all together. When she was drunk, he’d try to get her excited about what they were doing, but as soon as it would wear off, she’d “be a bitch again.”

“It was just so confusing and so difficult a situation,” O’Brien said. “I didn’t know what to do.”

“I didn’t want to be a rat ... because that’s even more dangerous,” she added.

She feared she might be trapped in the country or have her hands chopped off.

She was never physically threatened or hurt, but she didn’t know what might happen if she said no.

“I didn’t know this world,” she said.

She just wanted the days to pass.

The next weekend, a car came in the morning to pick them up and drive them to the airport.

But first, they headed back to the house to put on their customized underwear, which by now had more than two kilograms of cocaine stitched inside.

“I’m now officially in the drug trade,” O’Brien remembers thinking.

FEMALE MULES

Close to 14 per cent of women at Grand Valley Institution for Women are serving time for importing and exporting drugs, according to numbers provided by the Office of the Correctional Investigator.

In Canada’s six women’s institutions, five per cent of inmates are serving a sentence for importing and exporting, figures provided by the ombudsman for federally-sentenced offenders show.

Cases like O’Brien’s are “quite typical,” according to Daniel Brown.

Women are often an “easy target” for drug trade recruiters because of their socio-economic background, their race and other factors that make them “vulnerable” and likely to take an opportunity to make quick money, said the Toronto-based criminal defence lawyer with experience in drug importation cases.

Importers also suspect female mules are less likely to be stopped at the border, Brown added.

“So they’re specifically chosen because they don’t have criminal records — because they don’t fit the typical courier profile,” he said.

In addition to having clean records, women recruited are usually young and lured through the promise of cash and free travel — often to a “sunshine resort destination” in the Caribbean or Mexico, said Arun Maini, a criminal defence lawyer for more than 20 years and a former federal prosecutor in Brampton.

Typically, the introduction to the trafficker occurs in a “seemingly legitimate way,” like an encounter at a club, a gym or through a family member or friend, said Maini.

After trust has been established, the woman is offered a trip or a chance to make some cash, he said.

“It often sounds too good to be true, and it is,” Maini wrote in an email. “But the target is usually too naive or trusting to question it, or is willing to set aside her suspicions.”

“It’s a bit like human trafficking ... except that instead of being forced/persuaded to trade sex for money, the transaction involves drugs,” he added.

Women are often encouraged to participate for a variety of reasons, said Brown.

“They’re told that there’s no risk they’re going to be caught, and there’s normally some financial benefit for them at the end that’s menial in relation to the amount of profit that the actual person behind the plan stands to make on the sale,” he said.

Some of the women are considered “expendable,” Brown added.

“They normally have a number of women cross the border carrying drugs, and they hope that the border security’s simply not going to catch them or not going to catch all of them and those that do end up as casualties of the process,” he said.

Given the profitability of drug trafficking — especially cocaine, heroin, fentanyl and other synthetics — traffickers can afford to recruit couriers and absorb losses when some are intercepted by authorities, Maini said.

The use of “young, naive women” to import drugs has been going on for decades, he added.

Once the arrangements are made and the ticket has been purchased, Maini said women can be faced with threats to herself, her friends or her family if she tries to back out.

“Too embarrassed or scared to walk away, she holds on to the belief that she will not be caught,” he wrote. “And given how busy airports are, couriers often do make it through.

“Some will enjoy the easy money and do it again.”

The person arrested for importing is typically not the one who comes up with the idea to commit the crime or who stands to benefit financially from the sale of the drugs, Brown noted.

He pointed to a 2003 case R v. Hamilton (and Mason) in which the trial judge took into account circumstances faced by black women when delivering the reasons for sentencing these drug couriers in a way that would keep them out of jail.

The case was overturned at the Court of Appeal of Ontario, sending mules trafficking large amounts of drugs to the penitentiary for a significant period of time, which “really set the tone for the sentencing policies over the last 10 or 15 years,” he said.

“So when we have somebody in jail who says ‘There’s lots of others like me,’ it can all really be traced back to the decision in that case to overturn one judge’s attempt to keep these vulnerable women out of jail and the ramifications are still rippling through the court system today,” he said.

FACING PRISON

O’Brien’s bail conditions meant she needed a note to go anywhere except her mom’s house and work and she couldn’t use drugs.

But it didn’t prevent her from drinking. For the first few weeks after her release, she was holed up in her room drunk.

“There was a lot of angst in the beginning,” said O’Brien’s mom, Heidi.

O’Brien was scared about what might happen to her if the higher-ups from the drug world found her. She slept with weapons in her bed and took self-defence classes.

But after she was caught breaching her bail conditions by going out for cigarettes without a note, she was thrown into the Barton Street jail and her mom had to get her out.

She knew she had to clean up her act.

She didn’t want to let what happened dictate her future.

She managed to live a double life.

She spoke at events at the Hamilton Public Library and Communitech in Waterloo Region as well as on a panel on building a personal brand.

She also started to attend several treatment programs, including ones through the Centre for Addiction and Mental Health, for more than a year and a half.

Once she knew she would be sent to prison, she told the people who worked for her what was going on.

She worked with clients until a week before she was scheduled to surrender and then tied up loose ends with her social media company.

She had hoped her employees could take over the business but it was too difficult to communicate with O’Brien while she was incarcerated.

Two-and-a-half years after O’Brien brought close to five pounds of cocaine into the country, it was time for her sentencing hearing.

In 2017, she had entered a guilty plea and understood the severity of her crime.

But the case seemed to drag on forever — from the preliminary hearing, to having her case separated from her co-accused’s so she could be tried on her own, to changing judges, to getting the prosecutor to agree to a joint sentence.

Despite her plea, it still took close to a year for her case to work its way through the court system.

She knew she was going to prison — the question was for how long?

In his reasons for sentencing, Justice Bruce Durno said the joint submission of four years was appropriate given O’Brien’s case had “significant distinguishing factors from many others.”

Importing is a “serious offence” that involves “planning and deliberation,” and the amount in O’Brien’s case is “significant,” he said.

But there are also “some very significant mitigating circumstances, some very unusual for this type of offence,” including O’Brien’s guilty plea, which is “indicative of remorse and the potential for rehabilitation,” he said.

Durno pointed out that O’Brien admitted her involvement to Canada Border Services Agency early in the process, which he said is “rare,” and that she has an “enormous” amount of community support as reflected in her letters of support and the number of people in the courtroom on the day of her sentencing.

“It shows a number of things: That there are those in the community who will assist her, and it also shows her background, how the offence is out of character, the significant contributions she has made and the potential she has to make further positive significant contributions,” he said.

He also said he accepted the role O’Brien’s drug and alcohol addiction played in the offence and noted the steps she took afterward to address this.

On Jan. 16, 2018 — her mom’s birthday — O’Brien was taken into custody and her sentence started.

That’s when her “new life” began.

“Now that I’ve accepted it, this is going to be my time to change and start over,” she recalled thinking to herself.

Having played basketball growing up, she felt a game reference best described her situation.

“I had full-court press,” she said. “But now I was done playing defence and it was time to take the offence.”

Her lawyer advised her she would probably spend 10 months in custody.

She saw this as just another hoop she had to jump through. She was determined to make productive use of her time.

“I knew I’d be able to do something and turn my life around,” she said. “I knew that I was really good at finding ways to accomplish things because that’s what entrepreneurialism is — you jump through hoops.

“So I was like this is just another hoop. This is just another place I’m living, and I’m going to use it as a way to learn from it but also share my story because at the end of the day, everyone thinks that it can never happen to them. I was one of those people that looked at those signs at the airport and was like, ‘Yeah, what idiot wouldn’t pack their own bags ... how could this ever happen?’ But then you don’t realize it doesn’t just happen like that.”

Back she went to Vanier, which was “pretty horrific,” O’Brien wrote in her blog.

Inmates get 15 minutes of outdoor exercise — “yard time” — a day. She was served previously frozen and processed food served on trays and didn’t sleep well in her cell because the lights are never turned off.

Ten days later, the paddy wagon came to pick her up and take her to her new home — Grand Valley Institution for Women, a women’s federal prison in Kitchener.

While on bail, O’Brien volunteered with an organization that employed women who had been to prison. She met someone who had done time at Grand Valley for importing.

“She was kind of like my coach,” she said.

Through researching life behind bars and speaking with this woman about her experience, she learned more about the prison and was happy to be headed there.

IN CHAINS LIKE AN ANIMAL

The paddy wagon with “cushiony seats” has two sides lined with inmates.

When the 50-kilometre trip from Milton is over, they get out at the facility on Homer Watson Boulevard with their hands and feet shackled to one another.

“You shuffle up because obviously it’s hard to walk, like you’re in chains like an animal,” she said.

The shackles are removed, and the inmates are directed to stand against a wall while drug-sniffing dogs are called in.

After waiting for guards, inmates enter the facility where they are strip-searched.

Once checked in, women have their palms printed — O’Brien was asked to “karate chop” — and their photos taken for an identification card that must be carried with them at all times.

Any belongings O’Brien carried with her at Vanier were confiscated, including a winter coat, because it had a hood.

SETTLING IN TO HER NEW HOME

As O’Brien struggles to get her belongings inside her new home, one of her roommates offers to help.

“House 5” — one of the prison’s 16 “cottages” where 10 to 12 women live together and prepare their own meals — is a medium-security unit where she will spend the next four months.

The living room has a plum couch with a metal frame that “looked like something you would see in the lobby of a retirement or funeral home,” she wrote in a journal entry at the time.

In the kitchen, there is a refrigerator along with a metal table shoved against a wall with three plastic chairs underneath.

The five inmate bedrooms are up 14 carpeted steps. At first, O’Brien has to share a room but gets her own as soon as some of her housemates transition out of the two-storey home.

Thankfully, a woman she met in the holding cell when she was first arrested at the airport happened to be transferred to Grand Valley at the same time and became her roommate.

The room she shares is 15 feet by 15 feet, with two beds, a desk and cupboards with shelves below.

A spacious bathroom contains a tub, a massive mirror and a sink area.

At first, O’Brien felt isolated and lonely.

It was three weeks before she could to talk to her family. In what’s dubbed the “quiet period,” inmates submit phone numbers they want to call to Correctional Service Canada. The agency has to connect with the people before inmates can call them. Inmates also have to load their phone cards with money.

Each house has their own land line.

Inmates in medium- and minimum-security units have access to their own food they order off a more than 400-item grocery list that contains staples like eggs and sugar, fresh fruits and vegetables like apples and broccoli, baking supplies, spices, canned goods, cereal, frozen meat as well as halal, gluten-free, vegan and vegetarian options.

Each woman is given $38.01 for groceries a week.

In the beginning, it doesn’t seem like a lot of money, but it’s easier to stretch once you stock up on spices and dry goods, O’Brien says.

“The budget really stressed me out the first few weeks and I even went to see the psychologist to help me,” she wrote on her blog. “It’s not that I didn’t know what to eat because I definitely did, it’s just that I had no idea how to spread out the $38.01 over everything I needed.

“In real life, I would spend that on an ahi tuna salad and some truffle fries.”

In a few weeks, the anxiety passed with some help from her housemates and her counsellor.

In O’Brien’s house, the knives and scissors were chained to the wall. The guards locked them in a cabinet at night.

When inmates arrive, they’re given $30 as a “start-up allowance.” They line up to buy canteen items, but on their first day, they get to jump to the front of the line. On the Friday night she arrived, O’Brien bought Diet Pepsi, chips and soap.

With no real money inside, O’Brien said inmates would resort to the “grey economy,” trading groceries or hair braiding for canteen items, trading shoes for protection and completing homework for stamps.

Living with roommates means having to navigate another person’s behaviours.

But unlike her days of shared housing in university, some women were more violent than others, which made the roommate experience a tad different.

“You wouldn’t hit your roommate with a frying pan or a pot or throw something on them,” she said about her university days.

Day-to-day life for O’Brien inside prison became pretty routine and she started really digging into the experience.

She signed up for all the voluntary programs she could get her hands on. Chaplaincy, computer, horticulture and parenting were among the courses she signed up for in addition to required correctional programs she had to take.

She took her forklift and WHMIS certifications.

In June, she voted in the provincial election as an inmate.

She even celebrated her 30th birthday on the “inside” — her first sober one in 15 years — where fellow inmates brought her a cupcake and made her a celebratory meal.

O’Brien also got a job as soon as she went in. She worked for maintenance, picking up garbage — a job not many people wanted so they were always hiring, she said. She made $5.80 a day.

Eventually she was able to start doing repairs around the institution, working directly with a guy named Paul. They did everything from laying baseboards, to installing ceiling tiles, to hanging drywall, to painting.

But in mid-May, O’Brien moved into the 40-bed minimum security unit that opened in 2015, which brought with it a job change as a librarian in the prison library as Paul didn’t do much work in the minimum-security unit.

She’d spend her days reading, writing, helping other inmates with their resumes and exercising. At night she would watch television in the building’s common area to give her brain a break.

Inmates were allowed their own televisions no larger than 19 inches as long as they weren’t able to able to access the internet.

She wrote and recorded a song called “Private Town” — a look at the positive aspects of prison — through the Pros and Cons Program, which brings together music professionals and federal inmates inside.

Family and friends approved by the Visiting Review Board would often visit O’Brien, and while she associated with her fellow inmates, she typically spent her evenings alone.

For someone who spent much of her time before prison surrounded by others, it was a welcome reprieve.

“It was good because it was hard to get a hold of me, so instead of people texting you all the time and wanting things or needing things, you literally got to focus on yourself,” she said. “If you really want to talk to me that bad, you’ll figure out a way to come and see me.”

On the day O’Brien started her sentence, she vowed off drinking and drugs.

Some people tell her it was a “forced sobriety,” but she disagrees.

She said she could have found homemade alcohol “brew” inside and that people snorted their pills and smoked banana peels and tea.

“There is a drug subculture,” she said. “I could have got anything I wanted.”

But O’Brien knew her drinking and drug use was a “huge factor” in what got her into prison.

“I knew that once I stopped that then my life was going to be really different, and I’m going to actually be able to reach my full potential.”

She is grateful the prison system in Canada afforded her the opportunities she wouldn’t have had if she didn’t make it out of St. Lucia.

While some inmates around her complained about their time there, at the end of the day, it’s prison.

“The law’s the law,” she said. “Canadian prison is so much better than any other prison, so I just had no time for people that complained or were just bickering.”

BOUNCING BACK

When O’Brien went to jail, she didn’t try to be someone she’s not.

She made all kinds of mistakes because she didn’t understand how the system worked.

She was late for a court date when the guards didn’t wake her up. She didn’t realize she had to have shoes to wear in the shower. She did things she didn’t realize were against the rules, like putting money in the vending machine (inmates weren’t allowed to handle cash) and opening the side door of her house, which was meant for correctional officers only.

But she had a good attitude, so everyone left her alone.

Her lowest point was when her parents paid a portion of her $50,000 legal fees. She doesn’t like to ask for help and struggled with the loss of her independence.

At the same time, she recognized she needed help.

She saw her time in prison as 10 months of rehab — a chance to get clean but also to start to think about what comes next.

She wanted to share her story with the hope of helping others before they got into the same trouble she did.

While she had written articles through her time in prison, she eventually launched a blog — typing up entries in the computer room, printing them out and mailing them to a friend to post online.

One night in April while lying in bed and staring at the ceiling, the idea hit her. She wanted to start a business that could teach people, give former inmates employment opportunities and keep the community safe.

She noticed inmates ordered kernels from the canteen and put their own spices on the popcorn based on what was available through the grocery list.

“Inmates can be really creative,” she said.

“Popcorn was like this simple blank canvas for women of all backgrounds to express themselves through different mixes of spices and other flavours,” she wrote on her blog.

Soon after, she asked friends and former business associates to send her market research about popcorn companies.

After she surveyed fellow inmates, she decided on the name — Cons & Kernels.

In July, Correctional Service Canada gave O’Brien approval to run her business.

She worked away at her business plan and goals, and by September, she organized her first event outside prison.

CSC granted her permission to promote the start-up at Take Back the Night in Hamilton.

“It was just nice knowing they supported it,” she said. “They actually believed in what I was doing.”

At the same time, O’Brien applied for day parole, which allows offenders to participate in “community-based activities in preparation for full parole or statutory release,” according to the federal government’s website.

She submitted her support letters and her release plan. She wanted to come back home — to Ellen Osler Home in Dundas, a residential halfway house for federally-sentenced women.

Her hearing was scheduled for Nov. 28.

APPLYING FOR PAROLE

O’Brien tells the hearing by video she’s as good as can be.

She tells the board what happened — from her move to Liberty Village, to her drug use to cope with her emotions, to the impact cocaine had on her business.

She speaks about the programs in prison that helped her. She sees now she could have asked for help.

She was too proud to think it was that serious and thought she could put the blame on someone else.

She didn’t recognize the warning signs until it was too late.

She had never been in an abusive relationship.

She was naive to what she was getting involved with. She had never been involved in organized crime and didn’t understand the risks.

“I knew what I was doing was wrong, and I just wanted to get home,” she told the hearing. “I wanted to get out of the country because I didn’t know what would happen if I didn’t.”

A parole board member asks about her DUI from 2009 in which she lost her licence for a year.

Would she be open to having to abstain from drinking establishments as a parole condition?

“Alcohol will always be (a risk factor), which is why I would welcome a condition on that end,” she said.

The board grants O’Brien day parole for six months but denies her full parole. She must abstain from drugs, alcohol and drinking establishments.

When she is granted full parole, she could live at her mother’s house or on her own. She would have to ask permission to leave the province. Some inmates with a drinking stipulation apply to have it taken off once they get full parole. O’Brien thinks it’s safer for her to keep it on.

Before she is eligible for full parole, which would allow her to serve the rest of her sentence in the community, she must build some credibility.

O’Brien understands.

“The day that I came here, I knew that I wanted to change and I knew that I would take every single step - hundreds, thousands of steps - that I was going to change my life 100 per cent,” she tells the board. “This has taught me the value of being a good person and having a good family, being honest with yourself, being honest with others, and not turning to substances because that just makes things worse. I think the more that I can share my story, the more that I can hopefully save people from going down the same path that I did because I have a pretty good network and I think people will listen to me. That would be my way of giving back ... I want to continue to share and be honest about it.”

FREEDOM

O’Brien got out of prison Dec. 3 after serving 10 months in custody.

“It was awesome,” she said. “It was just so freeing.”

Her mom picked her up at Grand Valley in Kitchener with McDonalds’ breakfast in the car. She had an Egg McMuffin, a hash-brown and a double-double.

Heidi had been to visit her daughter in prison countless times. But this time, instead of going through the security checks to get inside, O’Brien “prances out like only Emily can.”

“It was kind of surreal to be honest,” Heidi said.

The two women drove straight to the Dundas halfway house O’Brien will call home until at least June.

In addition to her parole conditions around alcohol and drugs, she has a curfew of 11 p.m.

But O’Brien doesn’t mind.

“Working in corrections I’m sure they’ve been lied to a lot,” she said. “If they have to cover all their bases, that’s fine, because I can provide it.”

She is now proud to be more than a year sober and continues to attend support groups.

By sharing her story, O’Brien doesn’t want pity.

She wants to prevent others from walking down the same path she did.

Her key message is this: ask for help when you need it.

“I think a lot of the time with social media you always think your life has to be perfect. People don’t like to share parts of their life that aren’t perfect, which is why I’m sharing it, because a lot of it is a facade and these issues are real.”

O’Brien knows how lucky she is that her family had her back.

“My family has literally been my life support,” she wrote on her blog. “What if I had no one to bail me out? Or worse, what if they didn’t even want to?”

She saw people in prison with children of their own who didn’t have any support.

Heidi O’Brien knows how much worse it could have been for her daughter.

“She could have disappeared,” she said. “All kinds of horrible things could have happened to her down there and I’d never see her again.”

“I got her back,” she added. “Some people don’t ... get their kids back.”

Emily would like to see changes to the justice system to address the root cause of the problem instead of “attacking the lowest hanging fruit.”

“I think ... someone needs to create some sort of system for people to get out of that situation,” she said.

Instead of arresting mules, she sees value in monitoring them to track and gain access to higher ups in the drug world.

“Why don’t you follow me out of the airport? It’s not stopping it because they just keep doing it over and over again.”

In the meantime, she’s working to build her business.

She’s had orders, hosted events and been meeting with former Dragons’ Den star and bestselling author David Chilton.

For now, she’s producing the popcorn herself with help from others here and there but she still hopes to hire other former inmates. She knows she’s biased, but she sees the value in employing people with records. She believes they’re an asset as they’ll appreciate the opportunity and be loyal to their employer.

In the meantime, she will soon start full-time work as part of the grounds crew at a Burlington cemetery to help fund the venture.

Heidi is “thrilled beyond belief” with her daughter’s personal and professional progress.

“I’m absolutely astonished at her get up and go,” she said. “She has a way of just making things happen when she wants to.”

Emily hopes to write a book about her journey. While on parole, she would like to travel Canada — maybe embark on a speaking tour, talking to high school students.

One day she’d like to venture abroad again.

Instead of destroying her, going to prison made her stronger and more resilient. She believes she has transformed.

Of course she didn’t expect to end up a prisoner in her 20s.

“Sure as hell not,” she wrote on her blog. “But I sure as hell won’t let it stop me from doing something good with it either.”

WOMEN OFFENDERS IN CANADA

Overall, five per cent of Canadian federal offenders are women, according to Correctional Service Canada.

Women offenders are more likely to have a higher incidence of substance abuse and mental health problems compared to the Canadian average, according to CSC.

Compared to men, federal women offenders are twice as likely to be serving a sentence for drug-related offences, according to the 2014-15 annual report of the Office of the Correctional Investigator, which provides independent oversight of CSC.

They also have a higher motivation for correctional intervention and potential for reintegration, the report says.

Women offenders were more likely to be granted day and full parole than men between 2005 and 2015, CSC says.

Most women offenders are serving a sentence of less than five years, according to CSC.

Statistics Canada figures show 300 incidents of cocaine importation and exportation and 70 adults charged in relation to these crimes in 2017.

Overall, Canada Border Services Agency seized 2,859,965 grams of cocaine/crack in 2017-18.

Welcome to Grand Valley Institution for Women

Grand Valley Institution for Women opened in 1997 with room to house 70 women.

Today, it is the largest women’s prison in Canada with a capacity of 215.

A portion of the property is fenced in but the minimum-security unit is outside the fence.

When they arrive at Grand Valley, inmates are handed a fan and a bag including bedding, pillow cases, sheets, towels, a bath mat and face cloths.

Each woman also receives a sweatpants, royal blue shirts, grey sweatshirts, six pairs of socks and underwear as well as two sports bras.

There is a process inmates can follow to have their own items sent in, called “getting your boxes.”

Hair dryers, tweezers, clothing without derogatory messages, strings and hoods, shoes, CDs, CD players and Nintendos are all permitted, O’Brien said.

O’Brien received her box, which contained several books, pencil crayons, CDs, a CD player and clothes, two months after she arrived. Others waited closer to five or six months for their items, she said.

Each item has to be logged on a list called an “Offender Personal Property Record” and removed if the inmate gets rid of it.

Any money inmates have can be transferred into an account but it can take weeks to register, she said.

Treats like pop, chips, gum, Mr. Noodles, Cheese Whiz, herb and garlic cream cheese and chocolate bars can be purchased from the canteen along with stamps, stationary supplies, hair products, cold medication, body lotion, tweezers and hair dye but inmates must use their own money to do so.