Katie Telford, long-serving chief of staff, is the last woman standing in Justin Trudeau’s inner circle

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At this point, “Gotta check with Katie,” is basically a Parliament Hill magical incantation.

She is the quiet voice that carries, the last person in the room, a first-name-only Ottawa main character.

Some prime ministers have employed their chiefs of staff as mercenaries for specific moments and replaced them when the situation demanded something different. Others have held their chiefs close for years as trusted consiglieres.

Katie Telford has outlasted them all.

She has run Justin Trudeau’s office since the 2015 election that swept the Liberals into power: eight years in October. She’s one of the most powerful people in the country by virtue of the fact that her tight bond with the Prime Minister runs this government, and Canada at large right now.

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That makes it especially vexing that there is such a resolutely unreachable quality to Ms. Telford.

Outside of her trusted inner circle, it can be tough to get a read on her because she’s so reserved, prone neither to the bombastic glad-handing that usually powers politics, nor to individual warm fuzzies.

Even in a room full of people who would very much like to talk to her, she skirts the crowd, performing a disappearing-in-plain-sight act that suggests her diminutive size is a favour the universe granted her. In meetings, it’s not uncommon for Ms. Telford to be the quietest person at the table, although that’s partly a reflection of the groundwork she does in advance and behind the scenes to set up her aims and angles.

But really, the main thing to know about Ms. Telford is that you can’t know much. When people describe what it’s like to work with her, all they can offer up is a series of pencil lines that stop abruptly short of any sense of flesh and bone.

In the early days, she was often a public face of the Trudeau government, doing interviews and speeches, but she’s now retreated entirely behind the curtain. For this story, The Globe and Mail spoke to two dozen people who have worked closely with her, many of whom were granted anonymity to speak freely, but repeated efforts to interview Ms. Telford herself came to naught.

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At first, this government presented itself very self-consciously as an ensemble cast. There was Justin and Gerry and Katie and Kate and Mike and Bill and Chrystia and Jody and Jane and all the rest – though the top of the marquee was always Mr. Trudeau, his principal secretary Gerald Butts, and Ms. Telford.

It was the bromance of the two men that used to capture the narrative energy in the circles where people get excited about these things. But everyone might have been mesmerized by the wrong duo all along.

The years have peeled away almost the entire original gang. Some took more layers of skin with them than others. Now, it’s only Justin and Katie left.

At this point, as the polls clobber the Liberals and they can’t seem to shake a staggering inertia, Ms. Telford’s longevity is evidence of the depth of Mr. Trudeau’s reliance on her – not a sign that her clock is running down.

You have these two people at the top of the Prime Minister’s Office, working in a high-stakes environment of unrelenting pressure and unpredictability. And now, with the announcement of his separation from his wife Sophie Grégoire Trudeau, Mr. Trudeau’s personal life is in profound upheaval, too, just as his political fortunes have never been grimmer.

At the very moment when it’s crucial to get some fresh perspective, the same qualities that make Mr. Trudeau and Ms. Telford so valuable to each other – the comfort and constancy, the unwavering degree to which they have each other’s backs – is precisely what might not be serving them well any more.

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It’s a common assessment that something important has gone awry in PMOLand since Mr. Butts resigned four years ago, usually blamed on the loss of his specific talents and skills since he was taken out by the SNC-Lavalin blast radius.

This is, to put it mildly, a different moment from that day in 2015 when the new cabinet strolled up the Rideau Hall driveway in golden fall sunshine that seemed to come straight from the props department.

The Prime Minister who surged from third place to win that election is now deeply unpopular with voters, and even his own caucus has gone surly, unloading their gripes to anyone with a keyboard who will listen.

The economy doesn’t seem able to right itself after the upheaval of COVID-19. Even before that once-in-a-century emergency, the federal government had been so spendy that it left itself little room for adjustment. There’s a housing crisis fuelling bone-deep resentment and anxiety, and it seems destined to get much worse before anything improves.

Conservative Leader Pierre Poilievre has declared himself both mascot and warrior for the masses who feel ignored, lectured, afraid and angry that something essential is slipping through their fingers no matter how tightly they grip it.

He has tapped something deep and real in the public mood, and Mr. Trudeau and the Liberals look frozen in place, unable or unwilling to respond better to the moment.

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The summer cabinet shuffle was advertised as a major reset, but given that one of the most common criticisms of this government is the tight-fisted grip the PMO and Ms. Telford maintain on every issue and decision, cabinet ministers might not have been the most relevant deck of cards to half-heartedly redistribute.

Mr. Trudeau has said time and again – because he’s been asked often enough that it’s surely starting to feel like a rude hint – that he’s not going anywhere and will lead his party into the next election. It’s equally clear that Ms. Telford is in it for the long haul. She’s already bested the next most durable chief of staff in a PMO, Jean Chrétien’s legendary “Velvet Executioner,” Jean Pelletier, who held the job for seven years and four months; most tenures are much shorter.

So a long-serving leader, beset by voter fatigue and accumulated sin, faces an upstart challenger the incumbents loathe too much to take seriously. If Mr. Trudeau or Ms. Telford were inclined to seek unconventional advice about the situation, Stephen Harper might have some harsh lessons about the error of viewing your opponent as a self-disqualifying dingbat.

As the Prime Minister’s top adviser, Ms. Telford’s job is a strange thing, because chief of staff is a role that exists on its own terms, in that it has a list of standard duties and lines of responsibility. But the specific shape of the job and qualities of the person who performs it are dependent on the elected official they serve; one is the photographic negative of the other.

A chief of staff marshals everything from the politics of caucus relations and public opinion polling to policy implementation and administrative duties like staffing. But it is also knowing how your person thinks, what they care about, and what they need to read and hear to make sense of things. It is being both the pipeline that carries everything to the boss, and the filter that determines what gets through.

“It is about sort of co-managing a life,” says Marci Surkes, who was chief of staff to Ralph Goodale as public safety minister, and later executive director of policy and cabinet affairs in the PMO. “From ensuring that the trains run on time to making sure that they have a sandwich when they need it, and a cup of coffee, and that they have their media lines. You’re their last point of contact before they do just about everything.”

If a politician and their chief of staff are puzzle pieces carved out of each other’s flanks, people who know them well identify two qualities of Mr. Trudeau that help explain his deep dependence on Ms. Telford.

First, contrary to his gift for working a room – a political skill more than one person describes as cultivated rather than innate – the Prime Minister is at heart an introvert who trusts very few people, and Ms. Telford is pre-eminent among them.

Closely related is the fact that when Mr. Trudeau trusts someone and recognizes that they possess expertise in an area he needs, he gives himself over entirely to that. At some point along the way, a benediction on all things from the chief of staff he has described as “hard working, tough, honest and wicked smart” became his security blanket: ever-present, reassuring, needed.

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Close observers also commonly explain Ms. Telford and Mr. Trudeau’s bond and working dynamic as a bookended push-pull. People start from the notion that they share a core set of values centred on the importance of feminist advancement and other forms of equality. But those same people quickly add that the other essential ingredient in the partnership is Ms. Telford’s devotion to the truth serum of good data and her willingness to tell the boss what he needs to hear.

“The saying is that you want the fearless advice and the loyal implementation, right? I’ve never met a staffer more fearless than Katie,” says Jeremy Broadhurst, who has worked closely with her on campaigns and in the PMO since Mr. Trudeau became leader a decade ago. “She will always be prepared to challenge a consensus in a room or a person who is senior, like the Prime Minister, if they are making what she perceives to be a mistake or making a lazy argument or an unfounded argument.”

But there’s an inherent contradiction there when you’re talking about two people who look at what the country needs in order to be a better place, and see the same thing. How do you speak truth to power – even if you want to – when you and the power source see things in fundamentally the same way?

This might be why in critiques of the Trudeau government, and specifically the functioning of the PMO and Ms. Telford’s role as chief of staff, the term “groupthink” comes up a lot.

In aviation safety, there’s a concept known as the “Swiss cheese model” that explains how accidents happen and how to prevent them. The idea is that complicated systems work together like slices of Swiss cheese stacked randomly on a plate. A problem in one system – a hole in one slice of cheese – won’t doom the whole project if the slice under or above it covers the gap. With airplanes, redundant systems and safety checks offer reassurance that a problem in one layer won’t cause a catastrophe because so many tiers of defence have been deliberately built in.

But working with people who like you and think similarly, and basically believe you mean well, is like stacking up pieces of Swiss cheese cut from the same block. When your blind spots line up, things slip through the gap.

There is no other way to explain, for instance, the howlingly dumb decision for Mr. Trudeau to go to Tofino, B.C., on vacation on the first National Day for Truth and Reconciliation in 2021. The only reasonable response to that idea, wherever it came from, would have been whatever is the PMO equivalent of chucking your friend’s car keys in the bushes if they’re bent on driving drunk.

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The common understanding of Mr. Butts’s and Ms. Telford’s talents and roles in the PMO was heart-versus-head, or narrative and tactics. So, the thinking goes, it’s no surprise the Trudeau PMO seems to have lost the plot since its chief storyteller resigned in 2019. A more straightforward explanation is that Mr. Butts was never replaced as principal secretary and the workload at the top is simply inhumane for one person to attempt.

But that makes it especially confounding that a near-universal complaint about this government is that everything is so closely supervised by “the centre” that absolutely every decision of any scale goes through Ms. Telford.

One person who dealt with the PMO at close proximity was struck by the intensity of the instinct from staffers to run everything past her, no matter what the adviser suggested. Someone else with extensive experience in senior government roles says flatly, “It is the tightest controlled operation I’ve ever witnessed.”

Another person points two fingers at the ceiling and loops them in little circles to mime what they viewed as Ms. Telford’s tendency to “pontificate,” which to them meant endless queries about whether people had thought about this angle or asked that person what they thought. Some people view that as her way of making sure everyone is heard; others see it as a way to delay decisions indefinitely.

People also describe being taken aback by the degree to which Mr. Trudeau’s every interaction is pre-briefed by Ms. Telford and even scripted out. One senior staffer was about to have a call with the Prime Minister to discuss a decision, and minutes before, someone from PMO tipped them off that they would be pleased with the outcome. The issue had already been decided by internal deliberation and the phone call was little more than courtesy theatre.

Even people who are generally fans of this government concede that issues and decisions are getting slowed down by some bottleneck at the top.

One common theory is that many of the star recruits who landed cabinet roles early on were new to politics, and that gave rise to the practice of checking with the PMO on everything. Rather than the training wheels coming off once everyone found their balance, it became ingrained habit.

However, another person with close knowledge disputes the premise that there is a traffic jam caused by Ms. Telford’s insistence on running everything off her own desk. There are 38 cabinet ministers all clamouring for their files, they say, and wheels must grind into gear across multiple departments for anything to happen. Their view is that what looks like a chokepoint that can be conveniently blamed on a control-freak chief of staff may simply be a frustration familiar to any preschooler at the playground: waiting your turn.

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It would be unsurprising if there was a tendency toward centralization and insularity in this government. Looking out for one another and listening to the inner circle – and only the inner circle – is how they came to govern Canada in the first place.

Back in 2011, when the Harper Conservatives won a majority, the federal Liberals were in pitiful shape. They’d been out of power for five years, had lost three consecutive elections, and their caucus had been whittled down to 34 MPs as Jack Layton’s NDP “Orange Wave” became the official opposition.

Mr. Trudeau had first been elected as an MP in Papineau in the midst of this flailing. When he began to seriously contemplate running for Liberal leader, the first person he talked to was Mr. Butts (who declined to be interviewed for this story). His second recruit was Ms. Telford, whom he’d met when she ran Gerard Kennedy’s earlier leadership bid in 2006.

Mr. Trudeau would eventually walk away with 80 per cent of the votes on the first ballot at the 2013 convention in Ottawa, and when the federal election campaign geared up, Ms. Telford was named campaign director and national campaign co-chair.

She consulted with Jen O’Malley Dillon, a Democrat strategist and one of the key architects of Barack Obama’s 2012 re-election campaign, then set about combining Democratic campaign school tactics with her own predilection for data.

“I love numbers because they don’t lie, and because numbers tell stories,” she explained in a fundraising video. This would become her reputation and identity – Katie loves numbers, numbers do Katie’s bidding – and it blew Liberal minds. From our current vantage point, when everything is optimized by some algorithm, that 2015 awe feels a bit like medieval villagers watching with mouths hanging open as a travelling shaman dazzles them with a shadow-puppet performance.

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To make sense of why Liberals anointed Ms. Telford their modern campaign genius, it helps to remember that the Conservatives had been miles ahead in data and campaign techniques for years, segmenting the electorate into personas like “Zoe,” the organic-eating downtown dweller (not even close to gettable), or “Dougie,” the twentysomething tradesman who loves outdoor life (very Tory-friendly).

The Liberals, in contrast, had been languishing in the political hinterland long enough that their experienced talent was half a generation out of the game. Ms. Telford’s focus on data provided both a practical campaign boost and the psychological reassurance that their party wasn’t roadkill after all.

Which isn’t to say that everyone was sold on the shadow puppets. Within the Liberal establishment, there was a lot of cranky second-guessing.

“Until I guess late August or early September, when our numbers turned around – as we thought they would – we faced a fair bit of internal discussion, shall we say,” says David McNaughton, the Ontario co-chair of the campaign, and later Mr. Trudeau’s ambassador to Washington. “In the early stages, it was really Gerald and Katie and I who were hanging in against a lot of people who thought that we were not running a good campaign.”

Mr. McNaughton had a name for them: “The boo-birds.”

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Ms. Telford, meanwhile, was using her truth-telling numbers to make the ground game a laser rather than a shotgun, tailoring their door-knocking and phone calls to the voters and households where it would pay off most.

Her favourite sessions were the RAP meetings (short for “research, analytics and pathways”) she convened multiple times a week, based on practices learned from the Obama campaign. They combed riding-by-riding data to figure out the relative strengths and weaknesses across the country, and where a tweak was needed. Who could use a fundraising or volunteer boost, and who was doing just fine? Where was there a strong ground game so that a visit from the leader might put them over the top?

“Politics, there are a lot of people who want to make it like the secret society, where it’s an enclave of brilliant people, and they go into a room and there’s all art and mystery to it,” says Mr. Broadhurst. “Whereas I think she really wants to say this is a science, as much as anything else.”

Ms. Telford often opened meetings by asking people, “What’s your number?” She still favours that as an ice-breaker and focus exercise. The number could be how many doors your crew knocked on that week or how many endorsements you landed from a certain sector – anything to which you could assign a quantity. Her goal was to keep people focused on data, but to reinforce that numbers don’t mean anything without a story.

The election was a thumping win that took the Liberals overnight from 36 MPs to 184 of them, with full control of the House of Commons.

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Ms. Telford’s status as campaign whisperer was on display the following year, when she delivered a keynote speech to a rapturous, packed hall at the Liberal convention in Winnipeg. That willingness to be in the window – unusual for a backroom operative – was prominent in the early years of the Trudeau government, when Ms. Telford, Mr. Butts and other key figures often did interviews and speeches. She described that visibility at the time as both the unavoidable reality of a social media age when no one can hide behind the curtain, and a feminist project built around a “see her to be her” philosophy.

And then, at a certain point, it simply stopped; staffers like her, who in an earlier generation would have stayed in the back rooms, returned to them.

In spite of her natural shyness, when she was on a stage with a microphone, Ms. Telford was a terrific public speaker – witty, a storyteller who made you feel like you were getting a confidential debrief, on message with enough finesse that it didn’t feel greasy. After their victory, when they went out together on a Liberal “roadshow,” Mr. Broadhurst always spoke first because there was no way he was going to follow an act like that.

“Despite the cynics who thought a positive message would never beat attack ads about our leader’s nice hair, that young people would never actually turn out to vote so we shouldn’t waste time there, we persevered, we worked hard,” Ms. Telford told the Winnipeg crowd in 2016. “And I think it turned out pretty darn well.” She delivered the last line with a crooked little smirk of conspiratorial understatement.

The boo-birds had been silenced, inside the tent and out.

The harrumphing establishment of this party they had raised from the grave had been proven wrong. The sneering opponents who had dismissed their leader as a brainless dauphin had been vanquished. They had taken a third-place party and fashioned a majority government out of it, led by a grinning, hugging, energetic young Prime Minister on his way to becoming a global celebrity. Not only had their scrappy little team of believers done it, but they had done it in their own dazzling new way.

As teenagers, most of us go through a phase of thinking our parents are out-of-touch buffoons who make the sound of a washing machine when they talk. Eventually, you realize you’re not as smart as you thought and that the talking washing machines know a few things, and life gets better for everyone.

But what if instead of gaining that perspective, everything went exactly as you predicted when you thought you knew everything?

Many close observers of this government make the same critique quietly that former finance minister Bill Morneau has made loudly: that the Trudeau crew was extravagantly uninterested in seeking advice.

“The decision not to rely on experienced insiders from previous governments may have satisfied the urge to demonstrate a new way of doing business,” Mr. Morneau wrote in his book, Where To From Here. “But it left open the possibility of rookie mistakes, an enduring problem for the Trudeau PMO.”

One well-connected Liberal heard complaints from experienced people that they would gladly have run boot camps with the new people occupying their old chairs, but there was no interest. Anything that smacked of the old ways was out.

Now, two things are true. Any old guard tends to be skeptical about upstarts, because it’s more comfortable to remain convinced that they could have done it all better. But also, the new-and-pleased-with-themselves are prone to getting a little high on their own supply and confidently making mistakes that someone who’d been around a bit could have easily helped them avoid.

This government has authored some howlers. There was the early scandal over $207,000 in moving costs expensed by Ms. Telford and Mr. Butts; the Aga Khan private island vacation; the farcical India trip, WE Charity handling a student support program; the appointment of David Johnston as special rapporteur on foreign interference.

What’s damning is not so much the individual circumstances of each of those cases as the fact that the potential landmines were so obvious, and yet no one in the room had the perspective to say, “Uh, this is a really bad idea and we should not do it.” Or if anyone did, they were overruled.

A government accumulating scar tissue as it ages is inevitable. What’s confounding about this crew is how many of their wounds are self-inflicted and caused by the same basic problem: They can only see themselves in a mirror, never through a window.

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Many close observers see Ms. Telford’s talents and skills as a perfect fit for campaign mode, but less so for governing. An election campaign is about building the best thing you can out of the Lego bricks available to you – people, money, time, polling, geography – and Ms. Telford’s naturally systematic brain is happy and adept in that mode.

Unsurprisingly, her political career was born and burnished on the campaign trail.

In 2001, she was in her early 20s and casting about for a path when she volunteered for a provincial by-election. Gerard Kennedy was a Liberal MPP helping out with the campaign, and she caught his attention immediately. “Very poised, very matter-of-fact, no bluster,” he says. “It was just very noticeable that somebody fairly young was keeping up and adding to what was going on.”

He was looking for a legislative assistant, so he hired Ms. Telford when the campaign ended. Over time, as her duties expanded, she started agitating to become his executive assistant; he slow-rolled it because he thought she was terrific and wanted to give her time and training to grow into things. Then one day she walked into his office and announced that it was time. “And I said, ‘Actually, you’re right,’” he says, laughing.

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He became education critic, and when the 2003 provincial election kicked off with sweeping education reforms as its centrepiece, Ms. Telford helped to run a substantial portion of the central campaign. When the Liberals won, Mr. Kennedy became education minister. It took several months for him to convince the premier’s office that his chief of staff should be the young volunteer who’d wandered in during a by-election a few years earlier.

Mr. Kennedy liked to improvise and routinely horrified his ministry by making spontaneous policy announcements. Behind the scenes, when he riffed, Ms. Telford would prod: How is that going to work? What comes next? What are the trade-offs? “She was always the one bringing it back to Earth,” he says.

In 2004, the education unions were hashing out new contracts with the provincial government and they expected the usual emissary – some middle-aged guy who would bark about what they needed and what they’d damn well get. Instead, Mr. Kennedy walked through the door with what appeared to be a high school student.

“They didn’t know if Gerard was disrespecting us by sending this neophyte into the room,” says Gene Lewis, general secretary for the Elementary Teachers Federation of Ontario at the time. “I remember a couple of them saying, ‘You’ve got to be kidding.’”

He and Emily Noble, president of the EFTO, sat across the table from Mr. Kennedy and Ms. Telford during the negotiations. The education minister was charismatic and high-octane, and Ms. Telford was his exact counterbalance: cerebral, quietly determined, subtly drilling down to understand what Mr. Lewis and Ms. Noble wanted.

“We really did underestimate Katie,” says Ms. Noble. “You could not in any way bamboozle her. She knew her stuff, she knew the issues, but in a very respectful way – she wasn’t fist-pounding.”

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Today, at this more established point in her career, those who feel like they know her well see Ms. Telford’s calm and reserved nature as a rare asset in the het-up world of politics. It gets her unfairly judged as unapproachable, they say, when they see her as highly attuned to the well-being of those around her in an absurd pressure-cooker of a workplace.

“I think that Katie is an introverted, thoughtful person. And so if you’re in the banking sector, and you have an important role, and she walked past you at an event, it’s not because she was snubbing you, it’s because she was lost in her thoughts,” says Ben Chin, a senior adviser in the PMO. “There’s sometimes that kind of misunderstanding, you know, is she cliquey? She’s not an outgoing person, but she’s a completely approachable person.”

But to those who don’t feel close to her, she reads as not just standoffish, but deliberately unknowable. This is exacerbated by a broad perception that there are simply different admission tickets available to Ms. Telford’s company: some people get to be in the inner circle and others are stuck at arm’s length.

The feelings inspired by the cool kids’ table persist long past high school. But given that Ms. Telford can grant access to the centre of power in the PMO and to the Prime Minister himself, this sense of a closed-off clique has ramifications far beyond simple resentment.

Most observers agree that the circle of advice and potential dissent around her and Mr. Trudeau – never particularly wide or varied in the first place – has contracted sharply. Some of this is simple attrition as people have moved on over eight years in power, but it’s also a product of time passing in a different way.

With an endless supply of crises and partisan arrows flying at you, it’s easy to slip into a bunker mentality in the PMO. It’s not impossible to see things objectively and keep seeking out bracing external input, but you have to actively fight to do so, and it gets more difficult with every year that goes by.

Instead, there is a sense that all the concentric circles surrounding this PMO are shrinking, leading to maddening own-goals. Even caucus is an intelligence source left on mute.

It’s several bus stops past ironic that a government that first captivated the attention of the country by labelling the Harper government as out of touch and divisive has turned out to have such a tendency to shove its own fingers in its ears and hum loudly when disagreed with. Listening to voices that had been ignored – including their own, as plucky iconoclasts – was the existential ground on which Ms. Telford and Mr. Trudeau‘s deep bond was built, and it’s what landed them in the PMO in the first place.

Somewhere along the way, what they could see and hear and make sense of narrowed like the picture closing to a pinprick at the end of a movie.

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Still, until very recently, there hadn’t been much public airing of Liberal grievances. There was little appetite for looking like a back-seat whiner or listening to them, especially when things were basically going well. After the intramural Liberal wars of the Chrétien-Martin period, part of the renewal of the Trudeau era was a declaration that there were no hyphenated Liberals with factioned loyalties any more.

Instead, this incarnation of the party has functioned as a cult of personality wrapped around one man and his control centre: Justin & Katie & Co. That sort of thing creates its own convenient gravitational pull – until suddenly, one day, it doesn’t.

Stifled resentment and thwarted autonomy have just started to bubble to the surface in earnest, with a raft of recent reports of internal discontent as the House of Commons is about to return.

It’s not hard to conjure a near future in which Mr. Trudeau’s popularity remains tanked, the party’s chances for re-election dim and still he insists he’s not going anywhere, and neither is his chief of staff. They would be doing that surrounded by a Greek chorus of the Liberal old guard who have spent the last decade feeling ignored while watching the new guys step on rakes lying right out there in the open, and a current generation that feels like it’s been parked on the back benches with duct tape over its mouths.

Then it will really be only Justin and Katie. And if you want to find out if anyone else still has your back, you sure will when there are a lot of sharp objects aimed at you both.

With reports from Stephanie Chambers and Rick Cash

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