Open this photo in gallery Steve Vogelsang, shown at Drumheller Institution in Alberta earlier this month, spoke with The Globe and Mail about the circumstances that led him to rob banks in Western Canada. He is serving a six-and-a-half-year sentence, but comes up for parole in March. Todd Korol/The Globe and Mail

If there was a moment Steve Vogelsang realized his metamorphosis to “scumbag” was complete, it came just after 9 a.m. on July 8, 2017. That’s when he walked into a Royal Bank in a strip mall in northeastern Regina wearing a fake bomb duct-taped to his chest. He was 53 years old. It was his first heist.

Mr. Vogelsang slid the teller – a husky, no-nonsense Prairie woman in her 50s – a note he’d printed at a nearby Staples. “Give this man $50,000,” it read.

“Please help me,” Mr. Vogelsang whimpered through tears. “They’ve got my grandson.”

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The teller, clearly unmoved, slammed $400 in 20-dollar bills onto the counter. “That’s all I got,” she snapped.

The tears, cardboard bomb and half-baked kidnapping were all a ruse, but Mr. Vogelsang’s fear was not. He was so freaked out that he fled without ever picking up the money.

Over the next five months, he robbed five more banks in Saskatchewan and Alberta – four of them in an eight-day stretch in October, 2017, the tail end of what he calls his “long fall.” In all, he amassed a paltry $11,265 from the heists.

In the 1990s, Mr. Vogelsang was one of Manitoba’s best-known broadcasters, covering sports for CTV’s suppertime news. The Saskatoon native went on to head the newsroom before leaving at 39 for Red River College, where he created one of the country’s top broadcasting programs. A number of Winnipeg reporters still privately credit their careers to him.

But by the time he was arrested in October, 2017, he was broke and living in his 12-year-old Ford F-150, his only remaining possession.

The behaviour was so bizarre that on social media, some speculated that an addiction, perhaps gambling or drugs, must be to blame. Even his lifelong friends were blindsided.

“This is a puzzling case,” Saskatchewan provincial court judge Lane Wiegers said before sentencing Mr. Vogelsang to 6½ years in prison, where he remains today. “You’re a 55-year-old man with no prior record who’s been productive and successful and well educated . … It’s not a typical situation one sees before the court.”

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Open this photo in gallery Bank surveillance footage shows Mr. Vogelsang, disguised with sunglasses and a hat, in one of the five robberies he conducted in Saskatchewan. Saskatoon Police Service

Reporters who knew him before his descent into crime say Mr. Vogelsang was a joy to be around. He never read from a script and always nailed the first cut. “He was a big, goofy, clowny guy,” says Rick Fickes, who worked with him at CTV, then known as CKY. “He was always laughing, always had a story to tell. His writing was superb, laced with lighthearted jabs at the athletes.”

TV news at the time was still formal and rigid. Mr. Vogelsang, who began his career in Prince Albert in 1989 before moving to Winnipeg in 1992, was provocative and spoke directly to the viewer. He referred to Edmonton’s CFL team as the “filthy Eskimos.” Often, his “plays of the week” were a lowlight reel, with NHLers tripping over the blue line and banking pucks into their own nets.

He saw that sportscasters alienated viewers by only talking to diehard sports fans, and made a point of addressing the uninitiated.

One of his more memorable pieces was about a one-handed star quarterback from Dauphin, Man. Another focused on the national volleyball team’s setter, a Winnipegger who worked as a concert pianist. Every time she stepped onto the court, she risked breaking a finger. “At the end of the day, people don’t care who won or lost,” he says. “But these stories stick with them.”

It was the last of the gilded age of local TV news. Mr. Vogelsang had a car allowance, a golf membership, a wardrobe supplied by Harry Rosen. He didn’t even pay for haircuts. The celebrity routine was part of the job, and he emceed hundreds of charitable events, and sat on the boards of the Humane Society, Winnipeg Harvest and the Winnipeg Symphony.

For years, there were billboards with his “big, giant head” all over Winnipeg, his friend Dean Sawatsky recalls. “Is that the size of your ego, Stevie?,” Mr. Sawatsky used to kid.

A sample of Steve Vogelsang's sports broadcasting from 1997.

But when the Jets left for Phoenix in 1995, a lot of the excitement of the job went with them. Mr. Vogeslang decided to move into upper management, taking over as CTV Winnipeg’s news director. He didn’t love it. There was no creative outlet, he says – instead, his job was to provide resources and administrative support to his staff. The internet had not yet taken hold, but he could see the writing on the wall: “A 60-minute newscast that came on every 24 hours was no longer a growth industry.”

Rather than captain a sinking ship, fate intervened. In 2002, Red River College opened a new campus in Winnipeg’s Exchange District and hired Mr. Vogelsang.

He was a hardworking, well-loved instructor, who once emceed the news competition he created in drag. On their first day, incoming students would introduce themselves. Mr. Vogelsang would go around the room, repeating every name without error, one of his students recalls. For years afterward, he continued meeting many of his former students, coaching them on career moves, putting in a good word with the right editors, the student says. Tammy Karatchuk, another former student, wrote on a blog after his arrest: “A reference from Steve Vogelsang was like the last golden ticket.” Another called him “the most inspirational teacher I’ve ever had.”

But after nine years, he began to worry he was becoming his own worst nightmare: a journalism instructor out of touch with the industry. When Laura, his wife of 20 years, was offered a job in Nelson, B.C., where they had bought a retirement property, they decided to make a move. He could teach communications at the local college. It was just the two of them – they never had children. Steve would slow down. Finally, they would make life, not work, their main priority.

When he announced he was retiring, #SteveDontLeave trended on Twitter. More than 300 people packed into Winnipeg’s King’s Head pub for his farewell party, dubbed “Steveapalooza.” Mr. Vogelsang hired a band and a Hummer limo to chauffeur his family to the event. His closest friends flew in from Calgary, Edmonton and Saskatoon.

But as Mr. Vogelsang says from the visiting room at the medium-security prison in Drumheller, Alta., quoting James 4:6: “Pride goeth before destruction, and a haughty spirit before a fall.”

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Open this photo in gallery Mr. Vogelsang says career troubles, depression and personal secrets began to weigh on him heavily when he and his wife moved to Nelson, B.C. Todd Korol/The Globe and Mail

The transition to being a “total nobody” in Nelson was not easy. Mr. Vogelsang admits to being arrogant, even narcissistic, and his haughtiness rubbed people in the small, closely knit town the wrong way. “Everyone hated me,” he says plainly. In his three years there, he applied for 50 jobs and got one: a three-month teaching contract at Selkirk College. In desperation, he briefly found work at a Toyota dealership in neighbouring Castlegar before his declining mental health made it hard for him to get out of bed in the morning.

Throughout his adult life, Mr. Vogelsang had secretly struggled with depression. He swore Laura to secrecy. She figures he didn’t want anyone to know he wasn’t the brilliant, confident man they saw on TV. Even his closest friends were in the dark: “We grew up in the sixties on the Prairies among rugged, proud, self-reliant types,” Mr. Sawatsky, a former gym teacher, explains. “Men of our generation don’t talk about feelings.”

Mr. Vogelsang had been taking anti-depressants since 2008, but he felt so good leaving Winnipeg that he decided to go off them. Within a few months, he crashed into what felt like a “complete emotional collapse.” He was listless. He cried without provocation. Laura would come home in the afternoons and find him in his bathrobe. He spent his days sleeping, watching TV and smoking pot.

“You’ve got to fight it,” Laura would tell him, urging him to at least walk their dog, Mabel, or tackle the dishes. “You have to try." But all her husband ever wanted was to go back to bed.

Then, in 2014, Mr. Vogelsang was offered a job as vice-president of human resources for the Jets’ parent company, True North Sports and Entertainment. He and Laura decided to return to Winnipeg. “It seemed like finally I was landing on my feet,” he says.

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But the job didn’t pan out. He didn’t have the HR experience and quit before he could be fired. The disappointment, on top of three soul-crushing years in Nelson, pushed him over the edge, he says. “I was shattered, unable to function.”

And he was hiding another secret. While teaching at Red River, he’d fallen in love with a former student, an on-again-off-again relationship that went on for years. They’d split up when he left for Nelson. But when he returned to Winnipeg, they reconnected.

In May of 2015, he decided to tell Laura he was leaving. He had given himself one year to be sure it was what he wanted. While Laura was at work, he packed his stuff into his truck. He’d practised his speech dozens of times. He figured he had 90 seconds to do it without destroying her. “I was sobbing – almost hysterically,” he recalls.

He had changed, he told her, leaving out the part about the affair, which he thought would only hurt her more. Laura, who thought she was coming home for a dinner date at their favourite restaurant, was taken completely by surprise. (She only learned about her husband’s illicit relationship when she read about it in The Winnipeg Free Press after his arrest.)

His finances were also a mess. He and Laura had lost $85,000 on the sale of three properties they owned in Nelson. When they returned to Winnipeg, they bid high in a bidding war for a house they loved in River Heights, the city’s most desirable neighbourhood. Two years later, when they tried to sell it for what they’d paid for it, no one would bite. Mr. Vogelsang, who owed more on the mortgage than the house was worth, couldn’t stomach another big loss and tried to hold out a few more months for a buyer. He was teaching on contract at Red River College, but it wasn’t enough to cover the $3,200-a-month mortgage on his own. (The house was eventually sold after Mr. Vogelsang’s arrest.)

By 2016, he was lost in a fog of depression. His debts were mounting. He was lying to everyone. His Winnipeg friends were gone, lost to the divorce. He was packing on the pounds. He stopped answering the phone. His behaviour grew increasingly erratic. A new bitterness emerged. He was cruel, Laura says, and emotionally abusive. The “old Steve” was gone.

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His relationship with his former student had also grown volatile. It ended “spectacularly badly,” in 2016, Mr. Vogelsang says. The woman was granted a protection order, which Mr. Vogelsang broke three times. She told the judge she didn’t recognize him any more. No one did.

Then came more bad news. In August, 2017, a week before the fall session at Red River began, his boss texted to tell him his contract wasn’t being renewed.

By then, Mr. Vogelsang was destitute. He’d borrowed $10,000 from a friend, $2,000 from an uncle and another $2,000 from his college roommate. He had $15,000 in credit card debt. He was eating bulk rice and beans from Superstore. By October, the house was facing foreclosure. “Rather than do the right thing – declare bankruptcy and beg a friend to let me stay in their basement – I convinced myself that people had expectations of me. That I needed to maintain my image, my reputation,” Mr. Vogelsang says. “It was delusional thinking.”

That’s when he came up with a plan he now recognizes as absurd: rob banks to clear his debt and start over. He told himself that a bank was an institution, not a person. He wasn’t hurting anyone. “It’s completely insane thinking,” he says. “I didn’t recognize how far gone I was.”

And so began his spree, with that first bungled heist in Regina. He chose the RBC branch because it was located farthest from a city police station, giving him a few extra minutes to make his escape. Although he ditched the “bomb” after the first robbery, from then on, his MO rarely deviated.

He’d case a bank on the edge of a city and find somewhere nearby to park. He aimed to hit it near closing time, when fewer people would be inside. He would give the teller a note asking for $2,500, what he figured was a small enough sum for a teller to find quickly without freaking out or alerting anyone.

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He never ran. He’d park his car a few blocks from his target. After exiting with the cash, he’d shove his jacket and sweats into a garbage bin, then walk off in the blazer and jeans he wore beneath them, looking like the professor he once was. Once, Mr. Vogelsang ducked into a nearby Earl’s and watched police scream up to the bank as he ordered a drink.

Open this photo in gallery A surveillage-footage handout from Medicine Hat police shows Mr. Vogelsang before his arrest in October of 2017. Medicine Hat Police Service

On his last night of freedom, Mr. Vogelsang washed down a steak and escargots with a sturdy martini at a Medicine Hat chophouse. It was Oct. 20, 2017. He didn’t know it then, but he’d been made the night before. He’d hit a Royal Bank just before close, but he had made a big mistake.

Until then, he’d escaped from each robbery on foot. But that night in Regina, the RBC lot was empty. It was late. He was feeling lazy. So he parked in the lot.

On his way out of the bank, $4,100 richer, a car pulled in at the exact moment he was driving out. As the driver passed by, she locked eyes with him. Later, when the police came, she was able to give them a description of Mr. Vogelsang’s dirty red truck with its distinctive black cap.

The next day, the RCMP – working on a hunch that their bank robber wasn’t local – began checking the Gas City’s 13 hotels, looking for the truck. They found it behind the Medicine Hat Lodge, where Mr. Vogelsang had booked the jacuzzi room.

Around 3:30 a.m. on Oct. 21, he received a strange call from the front desk. A carbon monoxide alarm was going off, the receptionist told him. He was momentarily confused.

Then she asked him to “attend to” the front desk. Cop lingo, he thought to himself. The gig’s up.

The moment he stepped out his door, three armed officers rushed him from the stairwell. Nine more were scattered throughout the hotel. “Freeze!” they screamed. “Get on the ground!”

As he started to kneel, an officer kneed him sharply in the kidneys, flattening him. He lay on his belly, breathing into the beige carpet. It wasn’t fear or shame that washed over him. It was relief.

It’s over, he thought.

Open this photo in gallery Mr. Vogelsang says he'll always be remorseful for what he's done. 'This is how I’m always going to feel. None of that’s ever going to go away.' Todd Korol/The Globe and Mail

For the past two years, Mr. Vogelsang has occupied a nine-by-15-foot cell at Drumheller Institution, an aging, medium-security prison an hour’s drive from Calgary. Immediately after his arrest, when he was still in remand custody, doctors put him on anti-psychotics, but it took him a full year to get well. He recently saw the prison psychologist to make sure he was still sane. (She assured him he was.)

Now 57, Mr. Vogelsang says he has nothing to complain about inside. Respect has never been an issue. The inmates think it’s “cool” that an old guy like him had the “balls” to rob a bank. He’s made good friends. Most nights, three or four cellmates drop by to chat between dinner and final count. “The level of conversation is really quite good.” Everyone on the “range,” their cell block, knows not to speak to him from 7 to 8, during back-to-back episodes of Jeopardy, his favourite show.

He’s busy. He has a good job as a painter and works two shifts a day. He’s down 35 pounds since his arrest, and tries to ride the bike in the weight room every day. He gets his head shorn once a week by an inmate called Chad, who wears an apron fashioned from an old mattress pad.

In Block 10, everything is painted a minty shade of green, even the “bubble,” the officers’ watch station. The stale air smells of metal, chlorine and sweat. His two closest friends there are both older men. One is a deeply spiritual career safe cracker. The other is an engineer turned money launderer. He lost a third friend to a prison stabbing last summer.

At meals, Mr. Vogelsang tends to seek out the young guys. He tries to build them up and give them the attention and respect he senses few have been shown in their lives. There are few “evil people” in jail, he says. He believes as many as 80 per cent are there for committing crimes to feed their addictions. “It’s become a homeless shelter for addicts,” he says.

Three rules govern the place, he explains: Wait your turn, pay your debts and don’t rat anyone out. “That’s how we keep the peace. The distance to violence is shorter than on the outside.” The worst thing you can do, he adds, is back down from a fight. That’ll get you labelled a “goof.” Goofs are pariahs, punished with a communal shaming, the same method favoured by Prairie Mennonites. Right now, there is one goof on their block. Mr. Vogelsang figures he’s the only one in the prison still speaking to the man.

Mr. Vogelsang spent his first two years at Drumheller reflecting on how he got here. He says he is deeply remorseful for the shame he brought his family and for the trauma he caused the tellers he robbed. He has come to accept that the regret and guilt will stay with him forever: “This is how I’m always going to feel. None of that’s ever going to go away.”

But at some point in the past year, perhaps of necessity, he stopped caring what people think of him: “I have nothing left to be embarrassed about,” he says. “I have no image to live up to. I have nothing left to protect. I erased my entire life.”

However grim, there is also something freeing in this, he admits. “Very few people are called on to start over their lives from zero. I have to find meaning in that.”

His friend Kevin, the safe cracker, says he believes he needed to come here. “The person I will become will be a better version of me – less cocky, less aggressive, less angry, more humble.”

But it can be lonely. The third person to visit him in Drumheller was The Globe and Mail. Just two members of his large, extended family are still speaking to him: his sister and a step-brother.

Mr. Sawatsky is one of three or four friends who are standing by him. “I’m stuck with him,” Mr. Sawatsky jokes. “People make mistakes, some bigger than others.” If we’re honest, he adds, the distance that separates us from the damned is shorter than we imagine.

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As Mr. Vogelsang’s parole hearing draws nearer, he is starting to plan for his future on the outside. He knows he will never be welcomed back to Winnipeg. Saskatchewan is also out. His plan is to retrain as a safety inspector and settle in Calgary. Whether an aging ex-con can find work in a down economy is anyone’s guess, he says.

But he believes he still has something to contribute to the world. “This can’t be it,” he says.

That positive outlook is now enshrined on Mr. Vogelsang’s body – two prison tattoos he got last year that run down his forearms in a classic newsprint font. The artist, an inmate known as Smiley, is serving 30 years for violent crimes. The ink came from melted butter and ash.

“If you’ve only got a dollar, get your shoes shined,” one reads. As Mr. Vogelsang explains: “No matter how bad things get, you can always make the best of it.”

The second is a Joan Baez lyric. It has become a mantra. It’s what keeps him from surrendering. “Action,” it says, “is the antidote to despair.”

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