How, exactly, has Manitoba Premier Brian Pallister been able to ride out every controversy he's created in his decades-long political career?

Brian Pallister figures it must have taken his father, a lifelong farmer and a man of few words, more than a week sitting on his tractor to formulate a response to his son’s first political win.

It is 1992 and Pallister the younger has been elected to the provincial legislature. “He says, ‘Congratulations, boy. If you leave politics with your family and integrity intact, you’ll be a wealthy man with the experience.’ ”

While the judgment of history and the electorate are still pending, the Manitoba premier’s self-evaluation is more certain. He considers himself wealthy indeed—damn the howling critics and the string of controversies.

Pallister—a Progressive Conservative who upended 17 years of NDP rule when he was elected premier of Manitoba in 2016—is a difficult man to read; a public man who seems to need long periods alone in nature, reportedly unreachable by his staff. At times, he is self-effacing and dry-witted, at others, assured of his own righteousness. He waxes lyrical about the importance of journalism and becoming a writer, then goes on to explain why he’s suing the local newspaper.

He says he is an advocate for Indigenous people in Manitoba—particularly for First Nations women. Yet he’s alienated and offended the Manitoba Metis Federation and won’t apologize for using the term “race war” to describe tensions between Indigenous and non-Indigenous people over hunting at night.

He speaks about hard work and farm values like integrity; he’s been caught lying about taking out-of-country trips to spend time with his family.

He does not apologize. Pallister has maintained a role in the public eye for almost 26 years, an improbably long stretch for someone so prone to speaking his mind. Yet he has a Donald Trump-like talent for gliding through gaffes and controversies. He now sits among a growing rank of conservative premiers—Doug Ford, Scott Moe and, potentially, Jason Kenney in Alberta—reclaiming the mantle of right-leaning leadership at the provincial level in stark contrast to a Liberal Ottawa.

Pallister is a fourth-generation Manitoban. His great-grandparents homesteaded a plot near Edwin, Man., a short drive from Portage la Prairie. The brick home, built in 1913, still stands in a secluded patch surrounded by other small farm homes. It can be found at the end of a dirt driveway off a dirt road off a secondary highway, and it’s still owned by his brother, Jim. A wood sign reading “Pallister Trail” and a white-and-green wagon mark the path.

“We weren’t poor. I mean, everybody was poor, come on. It’s a rural environment with small farms. I think we were all in the same boat,” Pallister says in an interview with Maclean’s. “I don’t want to romanticize it or vilify it.”

Pallister describes a childhood that was not unhappy, but solitary, and certainly bereft of expensive charms and toys. He and his younger brother and sister kept each other company and made up their own games. During his early childhood, Pallister says he was the only boy in his grade in his country school and didn’t have many friends. “I still enjoy, very much, the freedom of hiking along a trail or going into the bush and exploring things like that,” he says. “That came out of being a child on a farm where we had virgin forest.”

With hard farm chores and little else to do, the Pallisters took well to sports. It was clear by his teens that Pallister wasn’t going to stay on the family farm—farming was in Jim’s blood, not Brian’s.

Jim went on to expand the family farm and now runs a large white-bean operation. Pallister studied at Brandon University, discovering his love for basketball there (he is an imposing six foot eight). He credits the game with giving him the confidence to pursue teaching and, later, sales. “I don’t think I could have gotten up in front of a group of students. I was very shy,” he says.

After a pep talk from his brother on the eve of his own wedding—“He says, ‘You’re always going to be in good shape, you’re going to be successful and you’re always going to have good friends, but you’re never going to have a relationship if you don’t stop just working and playing ball’ ”—Pallister set off to do some soul-searching, ironically while still playing ball—fast pitch softball, this time—during a stint in New Zealand. “This sports experience was an amazing time for reflection and planning, and I reflected not just on what he said, but on my life goals,” Pallister says. “My spiritual goals, my physical goals, my emotional goals . . . I made an actual chart.” Politics was not on it.

About a year after he returned to Canada in 1983, Pallister met Esther, who became his wife of 35 years. The pair bought a historic house in Portage la Prairie and fixed it up. They built up their business, selling insurance and financial advice, while Pallister got more involved in community politics. He became particularly engaged when the federal government announced it would cut the air force base in Portage.

Around that time, the MLA for Portage la Prairie resigned, and Pallister and his wife weighed a run for the seat. “We had just expanded our business and had a one-year-old. I will always remember that night we decided. I did a Ben Franklin thing and made a list, reasons for and against,” he says. The reasons against were numerous. It just didn’t seem like the right time.

Pallister tears up when describing what happened next: Esther turned to him and said, “When would be a better time?”

“That changed everything. I had decided that this was not going to happen. She hit me with the duty that my mother had instilled. You’ve got to do this, you can’t not do this. You’re needed now,” Pallister says. He won that first election in 1992, and every one—except one—since then, with margins as high as 70 per cent.

The election Pallister lost came in the late ’90s, when he found himself on the losing side of the split between the Reform Party and the Progressive Conservatives. In 1998, he launched a long-shot bid against Joe Clark, Hugh Segal and David Orchard for the leadership of the federal Progressive Conservative party and lost, finishing fourth on the first ballot.

He went on to win the seat for Portage-Lisgar in a bitter race under the Canadian Alliance banner in 2000, then sat as a Conservative MP. Although he was appointed parliamentary secretary on a number of files, Pallister never made cabinet in Stephen Harper’s government—a fact he largely shrugs off today. “I would rather people ask why I wasn’t in than why I was,” he says. He wasn’t actually there for long. The Harper government was elected in 2006. By 2008, Pallister had announced he wouldn’t seek re-election.

At the time, he said he planned to retire from politics and return home to Manitoba in time for his daughters to develop a relationship with their surviving grandparents, but politics is a strange addiction. Instead, Pallister returned to Manitoba and quickly became disillusioned with the direction of the province under the NDP.

And, well, there was an opening.

Greg Selinger had taken the mantle of NDP leadership from Gary Doer in 2009 and, by most accounts, Selinger’s reign was both gaffe-prone and fractious, culminating in a caucus coup and leadership race in which he succeeded in replacing himself. Selinger managed to cling to the premier’s seat, despite often earning himself the title of the country’s least popular premier. Whoever succeeded outgoing PC leader Hugh McFadyen would have a clear-cut path to power.

In 2012, Pallister ran for the position and won. By several accounts, he was a hard-driving leader who pushed his caucus to outsell and outwork their NDP competitors. “He’s always been that ambitious—he wants something, he goes out and gets it and he works hard. It doesn’t matter if it’s business or in sports, he always works very, very hard, and with a goal in mind,” says Earl Edmondson, who has worked with Pallister on his campaigns since 1992.

While the PCs were able to easily upend the wildly unpopular NDP in 2016, Pallister only ever seemed to inspire tepid approval from Manitobans.

According to the Angus Reid Institute, Pallister was the second-most-popular premier in the country after he was elected, but his approval rating has slowly but steadily declined since then. Only two years into his mandate, he has an approval rating of 37 per cent. That puts him in the middle of the pack in comparison to the rest of the country’s premiers.

By the time he was the presumptive replacement for Selinger, Pallister was also attracting increased scrutiny for his wealth, lifestyle and personal quirks.

In 2012, he purchased a lavish Tudor-style mansion in an upscale Winnipeg neighbourhood on the banks of the Assiniboine River for about $2 million (the average house price in the city is about $300,000). Built in 1935 by a grain magnate, the 9,000-sq.-foot home features a multiple-car garage, sloping roofs and castle-like stonework. “It’s restored beautifully. It’s just a wonderfully comfortable, beautiful home,” he says. “It’s a class-warfare thing—it’s been a traditional NDP tactic to try to generate a sense of deprivation. If someone else does well, it must mean they have a negative quality or they are unhappy or some such myth.”

At the time, Shannon Sampert, an associate professor of political science at the University of Winnipeg, criticized the premier, pointing out that the message he was trying to convey—that hard work could land a mansion—was a “continuation of this neoliberal idea that if we just really work hard we’ll all do well, and that’s not the case. We can’t all become millionaires. It all comes down to who you know, who you hobnob with—that’s how you get ahead in the world,” she said. “It’s kind of insulting to everyone else who works hard but lives in west Winnipeg in a $150,000 house.”

“I got where I got in my life by working hard and smart in a focused way, and I started with basically nothing,” Pallister says. “Who do you want as premier: somebody who started with something and squandered it or somebody who started with not much and made something of themselves?”

Pallister controversies tend to follow a familiar cadence, not unlike how the housing hoopla played out: an inflammatory comment or revelation, public uproar, a refusal to apologize, a return to stasis.

Take Manitoba’s ongoing night hunting controversy. A modern iteration of Indigenous constitutional and treaty rights to hunt food and prey has taken the form of night hunting—using a spotlight to shine a light in the face of an elk or deer, stilling them before the kill.

The practice is controversial and dangerous, with farmers complaining about night hunters venturing too close to private property, as well as human fatalities associated with the practice. The Pallister government introduced a bill last spring to curtail night hunting, legislation that has been opposed by First Nations groups.

In early 2017, Pallister warned of a “race war” if night hunting were allowed to continue. At first, David Chartrand, president of the Manitoba Metis Federation, assumed Pallister had simply suffered a slip of the tongue. But the premier doubled down on the comment, convincing Chartrand that the comments were racially motivated. “It’s definitely a race issue that is happening there,” Chartrand says. When asked to clarify, Pallister’s clarifications “came out even worse,” he says. “Then I knew right there that this guy was playing a race card.”

Pallister still defends this comment. The context is often omitted, he insists, but he stands by his position on night hunting. “It was a comment in answer to two white guys who said they were going to take their unlicensed shotguns and shoot the next Indian who walked across their field . . . I looked right at them and said what we don’t need here is a race war in response,” he says.

Pallister also defended a dryly mocking Christmas message recorded in 2013 wishing “infidel” atheists well during the holidays. “That’s what is so funny, how strong atheists are in their belief that I’m primitive if I believe in God. I got so many attack emails back, you have to laugh. I mean, why do you care?” he asks. “It means non-believer. I mean, look it up. An infidel is a non-believer. I mean, I know there is another context in the Middle East, I get it.”

Pallister also continues to be dogged by questions about the amount of time he spends at his vacation property in Costa Rica.

According to records obtained by the CBC, Pallister spent about seven and a half weeks in Costa Rica in 2016—though Pallister said he’s spent only five weeks abroad since he was elected that year. The broadcaster reported that he spent 10 weeks there in 2015 and more than 12 in 2014.

During floods in 2014, Pallister claimed he was attending a wedding in Alberta, but he later had to admit that he was actually vacationing in Costa Rica.

Maclean’s tracked Pallister to the villa in 2017. The premier still spends several weeks a year there, though he considers his time away a working holiday and insists that staff can always reach him.

More recently, Pallister got into a public spat with the Winnipeg Free Press when the paper ran a story claiming he owed the Costa Rican government back taxes on the home.

Pallister adamantly denies this and has served the paper a notice of libel. When asked if this response was a tad disproportionate, he says: “You’re talking about my relationships with clients. I’ve worked with their families for years and years and they put it out there that I’m not paying my taxes? Come on, that’s not fair. And it’s not based on accurate reporting, so I’ve got to defend myself.”

The newspaper says it stands by its reporting.

Many of those who work with Pallister have high praise for him. He is determined, witty and has even been known to write songs—and sing them—when he’s around trusted friends and advisers.

Eric Dalke, who worked with Pallister as his legislative assistant in Ottawa and later on his leadership campaign, believes Pallister is an exceptionally hard worker who holds those around him to the same ethic he demands of himself. Dalke remembers the premier sending back a draft of a press release a dozen times, until he was exhausted with the project. “He wanted to get things perfect,” Dalke says. “I [eventually] threw in this clever thing and sent it back to him, and you could hear him exclaim from the office across the hall that he really liked it—finally we got it. Definitely, he will work things to the bone, but I liked that, I liked to be pushed really hard.”

The relentlessness does not go over well with everyone. Inside the legislature, there were rumours that Pallister would award a wooden buffalo—a “buffalo of shame”—to MLAs who screwed up or failed him, although a spokesperson for Pallister says the story is the invention of a disgruntled staffer.

From the other side of the aisle: “Things aren’t adding up, and you can’t quite put your finger exactly on what it is,” says Dougald Lamont, leader of the Manitoba Liberal Party. “For whatever reason, he is always the odd man out.”

Philip Houde, the premier’s chief of staff, is one of Pallister’s biggest fans, yet says that the man “doesn’t fit the mould a lot of people see in their leaders. He likes to have his own principles in how he governs himself and he isn’t going to change them, no matter what people think he should do.”

Another controversy: In a shocking move earlier this year, most of the board of the publicly owned utility Manitoba Hydro resigned en masse. Led by Sanford Riley, a well-respected businessman hand-picked by Pallister, the board—largely considered to be aligned to the PC government—had been brought in to fix Hydro’s enormous financial problems.

Pallister says the Hydro board resigned when he rejected a proposal to pay $70 million in “hush money” or “persuasion” money to the Manitoba Metis Federation.

According to Manitoba Hydro, the 50-year agreement was intended to address Indigenous rights connected to various transmission projects, including the Manitoba-Minnesota line. “What happened is we’re not going to pay people not to object to a hydro project,” Pallister says. “Riley didn’t get the answer he wanted on an issue where cabinet gets to decide.”

Riley has a different version. He says the proposal to the Manitoba Metis Federation had been sitting on the premier’s desk unanswered for months. Over the past year, the board and the premier had ceased to communicate as the depth of the financial quagmire Hydro faced became clearer. “At that stage, it was clear to us that we didn’t have the confidence of the premier for whatever reason. He didn’t like the answers we were giving him,” Riley says.

Riley contends the board was on the verge of resigning when he received a call asking him to shift his role to another Crown corporation.

That was the last straw, Riley insists, prompting a mass resignation. “I thought it was cynical of him to shift the ground to the Manitoba Metis Federation when the real issues were the financial problems at Hydro and his unwillingness to come to grips with them. And that manifested in an unwillingness to have any kind of dialogue with his board.”

Pallister responds by saying that it isn’t the premier’s job to meet with boards—that is what his ministers are for. “That’s fine, that’s fine. His perceptions are his,” Pallister says. “We disagreed.”

Chartrand sides with Riley’s version of events. He says he was one of Pallister’s supporters until the premier took office. After that, the meetings and solicitations stopped. “He grabbed our file and said, ‘Here are the bad guys. It’s not me, it’s these guys,’ ” he says. “Then he fundraised on it. I couldn’t believe it. Why are you bringing something back that this country is trying to overcome? Racism, division, this style of politics . . . why the hell are you taking us down this road again?”

Chartrand believes that Pallister’s personality makes it impossible for him to concede a mistake. “His ego is so strong, so big, he will not admit he’s wrong. He will not admit failure. He will blame everybody else,” he says.

Late last year, Pallister got lost while hiking alone in New Mexico; while trying to reach his rescuers, he fell and shattered his left arm. The injury, and his near-fatal misadventure, wasn’t made public until several days later, prompting further complaints about Pallister’s penchant for going off the grid and offline during his long absences from Winnipeg.

Pallister jokes that getting injured while hiking alone is a “good way to receive unsolicited advice.” He insists he has nothing to apologize for: “The real mistake would be not hiking the Gila Wilderness. That would be the larger mistake.

“I have a dry sense of humour that gets me into trouble. I confront issues, that gets me in trouble. I’m plainspoken and I don’t think I’m likely to change now, and, yeah, that gets me in trouble because it’s politics,” he says.

The premier is also very defensive of his family’s privacy, which goes some way toward explaining his evasions on the Costa Rica trips, which Pallister considers sacrosanct family time. “I’ve got a strong relationship with the woman I met 35 years ago, and I am going to keep that. I have a strong relationship with two beautiful daughters, and I’m going to keep that, too,” Pallister says. His family remains close-knit. His two adult daughters still live at home on the family estate on the Assiniboine River, the home itself a testament to the fact that Pallister counts himself a wealthy man.

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