This week, Prime Minister Justin Trudeau and his Cabinet met for a three-day retreat in Hamilton to plan for the government’s legislative and policy agenda for the upcoming parliamentary session. One voice who wasn’t around the Cabinet table but may be in the near future is Charles Sousa. The former Ontario finance minister will officially join the Liberal Caucus next week after winning the Mississauga-Lakeshore byelection in mid-December 2022. 

While captaining a tight fiscal ship hasn’t been a top priority for the Trudeau government, Sousa’s impending presence may lend some much-needed fiscal credibility to its policy agenda, particularly if a cabinet shuffle places him in an influential role.

With a lengthy history in the business and corporate world, Sousa is almost a throwback to previous generations of Liberals from the banking and finance sector who would lose sleep over budget deficits. ​Prior to the byelection, Sousa sat or directed several boards, led numerous real-estate developments, and was involved in financial services consultations.  

“Most of the colleagues that called on me to do this run was to…be a strong voice, a positive voice to engage with the business community and the economic growth plans that need to be done in order to sustain the programs that matter to people,” says Sousa. 

Founding a small financial services company in 1982, Sousa went on to work in high-level positions at Royal Bank from 1987 until 2007 when he was elected as an Ontario Liberal MPP for the Mississauga-Lakeshore riding, named identically to its federal counterpart. 

Sousa became Premier Kathleen Wynne’s finance minister in 2013, and was described as “arguably the second-most powerful individual in the province.” That lasted until 2018 when he lost his seat, though by a closer margin than most other Liberal incumbents, who were typically blown out of the water in that year’s provincial election. 

Sousa’s re-entry into politics, this time federally, coincides with the Trudeau government’s professed plan for less-unbalanced budgets than usual as the Bank of Canada hikes rates to combat inflation. 

“I think he knows and understands the business community because he’s been part of it, both big and small. So I think that’s a good perspective to have in the Liberal caucus,” says Bob Richardson, a former Ontario Liberal chief of staff. 

However, with an election likely within the next three years, retaining Toronto’s suburbs might take precedence over reassuring the Chamber of Commerce. Choosing Sousa as the byelection candidate might have been Trudeau’s latest bid to convince Golden Horseshoe families not to vote Conservative. 

Richardson says Sousa brings “suburban sensibilities” to the table. 

“He understands what’s going on in communities like Mississauga, as an example, the growth that’s going on, what’s required from a transit perspective, some of the pressures that they’re having on services as well. I think having that knowledge is helpful,” says Richardson. 

Sousa was born in 1958 and raised first in Toronto’s Kensington Market before his family moved to Mississauga, where he still lives. He makes sure to point out that, like thousands of other GTA residents, he always made the daily commute to and from Queen’s Park as an MPP. 

When talking to people in his riding, Sousa says the primary concerns he hears about are the welfare of their families and being able to get good jobs, rather than partisan loyalty. 

“They don’t care if I’m a Liberal or a Conservative, they don’t care if I’m the mayor, or the counselor, or provincial or federal, all they care about is ‘What are you guys doing to get my life in order’,” says Sousa. “These people all have the same concerns, regardless of where they’re from.” 

A recent Abacus poll suggested more Canadians currently trust the Conservatives than the Liberal government to handle health care, the economy, and the rising cost of living. 

“Given where the Conservatives may be going…having someone who is aware of those bread and butter issues, those economic issues is going to be important, given the fact that the leader of the Opposition is also focused on those issues,” says Ali Ghiassi, Sousa’s former chief of staff while he was Ontario’s finance minister. 

Ghiassi says his former boss’s entry into federal politics reflects Canada’s changing economic climate, which commentators say bodes poorly for Justin Trudeau’s preference for deficit spending. 

“I think in the last 15 months, things have really changed when it comes to inflation…having a voice in the caucus that has heard from constituents at the electoral box in the last few weeks is particularly important,” says Ali Ghiassi. “I think the dynamics have changed, and I think the government is quite aware of that.” 

Wynne and Sousa’s Liberal government posted just one balanced budget during his five years on the job, perhaps against Sousa’s own instincts. 

A staunch free marketer and fiscal conservative as a younger man, Sousa’s views changed by the time he became a politician. However, he is still often described as more moderate than many of his colleagues. 

While Sousa did cut small business taxes while Ontario’s finance minister, he also helped craft one of the largest infrastructure spending plans in the province’s history, to the tune of more than $130 billion. 

“I’m not extreme at any spectrum of the political realm, so to speak, I am very much a centric guy,” says Sousa. 

With the Conservatives only needing to win a modest share of Greater Toronto Area ridings to defeat the Liberal government in the next election, Ghiassi says Sousa can help attract more centrist, and perhaps even some centre-right voters, to the Liberals. 

“Having someone with his background, both in the private sector and also in provincial governments where you tend to be a little bit closer to program delivery, I think would benefit the Trudeau government. Whether they choose to put him in cabinet is ultimately their decision,” says Ghiassi. 

Regardless of whether he becomes a cabinet minister, Charles Sousa is entering parliament as a different kind of Trudeau Liberal. Whether he leaves that way remains to be seen. 

A sure sign of the growing influence of the Runnymede Society is that, among the 100 or so of Canada’s brightest legal minds mingling before the group’s annual conference last weekend in Toronto, a Supreme Court justice can weave his way through the crowd, chatting casually, and go relatively unremarked upon.

It may be that the group has gotten used to these legal celebrities. Supreme Court Justice Russell Brown, who gave Saturday night’s keynote speech at the conference, is the third sitting justice in three years to attend the conference.

Since it was founded in 2016, the Runnymede Society has mostly defied easy descriptions, but its influence is becoming obvious, and 2022 may have marked a watershed moment for the Canadian legal landscape and the society itself.

Founded by the Canadian Constitution Foundation as a student organization to promote constitutionalism, fundamental freedoms, and the rule of law, the Runnymede Society has since spread across Canada into all major law schools.

The society can be loosely described as right-of-centre, and its members identify as libertarian, classically liberal, and conservative. But most of all, it’s the kind of group where the big laugh lines are inside jokes about constitutional interpretation.

“Everyone in first-year law school can tell you the Constitution is a living tree…” said Justice Bradley Miller, during a fireside chat that kicked off the conference on Friday. And, with a talent for comedic timing not commonly associated with judges, Miller let a long pause hang in the air.

“That’s mostly false,” added Miller, to a wave of applause and laughter.

Inside Miller’s joke is a clue to why the Runnymede Society has grown in size and influence at a steady rate over the last seven years.

It now boasts 19 student chapters and seven chapters run out of major Canadian cities. The last four Law and Freedom conferences have hosted Supreme Court justices, with three of them currently on the bench.

The panels at the conference focused on issues like the state of academic freedom and the provision in the Charter against cruel and unusual punishment, usually finding the intersection between legal wonkery and controversial political topics. Although most of these panels feature disagreement among the panelists, the discussion on the government’s invocation of the Emergencies Act last year found consensus that the Liberal government had overreached last year when it invoked the Act.

Like Miller’s subversive humour, the Runnymede Society has been poking holes in the broad and mostly unquestioned consensus in Canadian law.

“It’s kind of anti-establishment. The thing they have in common is that their views are not really reflected in the legal establishment today. But I think you’ll find just as active disagreement among members of Runnymede as you would between any of them and the establishment,” said Howard Anglin, who has served as deputy chief of staff to Prime Minister Stephen Harper and worked as a lawyer in New York, London, and Washington, DC, along with being a Hub contributor.

As debates over the use of the notwithstanding clause in the Canadian Charter burst open last year, some legal experts noticed that the debate wasn’t as one-sided as they expected. Smart academics argued that it was perfectly reasonable to use the notwithstanding clause, while most of the left-leaning legal establishment argued against it.

But some of the most heated debates came between Runnymede members. The society’s more libertarian-leaning members resent the notwithstanding clause for providing an escape clause on Charter rights, while more conservative members support it for pulling power back to the legislature, which is answerable to the people. Other members have context-dependent positions that depend on why the government has invoked the clause.

The sheer variety of interpretations was notable, especially in a world that hasn’t always welcomed viewpoint diversity.

Miller said the legal landscape in Canada has always been marked with “hostility to novelty and different lines of analysis, particularly in constitutional law.”

The idea of learning from U.S. originalist thought is met with “deep hostility,” he said, at least partly because it’s “unfairly related” to the U.S. Republican Party.

When Miller was appointed to the Ontario Court of Appeal in 2015, a year before Runnymede was founded, his defence of originalism, which puts an emphasis on the original meaning of the constitution, was met with outrage.

Now, at least among the conference-goers at the society’s Law and Freedom conference, there is a pervasive feeling that any opinion that can withstand the stress test of a friendly cross-examination is welcome.

The debate on the notwithstanding was invigorating for the legal nerds who engaged in it, but it also provided a crucial service to Doug Ford’s Ontario government, which was battling a monumental public relations crisis over its decision to invoke the clause.

It didn’t help that the Ontario government had used the notwithstanding clause to impose a contract on education workers who were attracting widespread sympathy from voters, according to opinion polls. On the legal question, though, the government was on firmer ground.

When journalists questioned the government and TV shows convened panel discussions, the conversation was more balanced. The Ford government could correctly say that experts were split on the issue, taking a little bit of the heat off the political firestorm.

“I think it’s very helpful because conservatives are used to getting crushed in the media,” said Anglin.

It’s unrealistic to expect the average voter to understand the nuances of Sec. 33 of the Charter, but they will notice if the battle among experts is being fought to a draw.

“In some cases, the best you can hope for [in managing political issues] is to get to the point where a normal harried person who’s consuming the news in 30-second drips, looks at it and sees that there’s somebody on one side and somebody on the other and then either forgets about the issue or lets their normal prejudices kick in, such as whether or not they like the politician or the party. In those cases the goal is to neutralize an issue, not necessarily to win it,” said Anglin.

Although some conservative politicians have recently taken great pleasure in skewering experts, they still seek that authority when unveiling a new policy idea.

“It’s very important to have media support and experts in third parties that can validate policy positions. It’s pretty crucial,” said Samuel Duncan, a vice president at Wellington Advocacy who has held senior roles in both Ford’s office and in the prime minister’s office of Stephen Harper.

“It’s always helpful to understand, from the government’s perspective, who’s going to be on the other side of this? And how loud are they going to be? Do we have a voice that can counter that, to try to make sure there’s a balanced perspective in whatever is being discussed?” said Duncan.

At the Runnymede conference last week and in the broader legal community there have been some tentative suggestions that there is a vibe shift underway.

It’s been noticed by right-leaning governments, who aren’t getting crushed in the media quite as conclusively as they are used to, legal academics, and even a Supreme Court justice.

“There’s a shift happening. And there’s already more room for different points of view,” said Geoffrey Sigalet, an assistant professor of political science at the University of British Columbia’s Okanagan campus.

“I think what’s happened is Runnymede has seriously started to shake things up. I think Runnymede is the key ingredient here,” said Sigalet.

If the current legal establishment is described as a collection of overlapping left-leaning groups that mostly agree on the idea of expanding judicial power and taking an expansive view of the Charter, they are starting to see some pushback from influential places.

At his keynote speech at the Runnymede conference on Saturday night, Brown said he has seen a shift in recent years towards more judicial humility.

“As to the other feature of the first 40 years of Charter adjudication—the large and liberal constitutional interpretation—the Court has shifted around the margins there as well. And so in a few recent judgments, we’re now seeing in the Court more restrained, intentionally grounded analysis,” said Brown.

Brown argued that there was nothing inevitable about the Court’s “large and liberal” interpretation of the Charter in the first 40 years of its existence and so there is nothing foreordained about the next few decades either.

“And this is where the Runnymede Society comes in,” said Brown.

“What you’re doing at the Runnymede Society is terribly important, because there is, at these events, a refreshing ecumenicism about these kinds of questions, and I commend you for that,” said Brown.

At the fireside chat on Friday, Miller also argued that progressive living tree proponents are starting to impose some limits on how far they take that interpretation. Miller wrote the majority decision at the Ontario Court of Appeal that upheld Ontario Premier Doug Ford’s move to shrink the Toronto city council. The Ontario Court of Appeal’s decision was upheld at the Supreme Court and Miller said there was a “living tree” argument available to any justice who wanted to reverse his court’s decision, but “nobody went for it.”

Some critics and proponents of the Runnymede Society have compared it to the Federalist Society in the United States, either as an ominous warning about the group or an optimistic hope for what it can achieve.

It’s an imperfect comparison, and one that some members of the group will shy away from, but there are some similarities. The Federalist Society has mainly functioned as a networking organization, pulling like-minded lawyers together to share ideas and help promote each other. That mission mirrors the goals of the Runnymede Society.

One major difference, at least at this point in the combined history of the two groups, is the wild, almost unbelievable success of the Federalist Society in getting its members appointed to the U.S. Supreme Court. The current, nine-person court contains six Federalist Society alumni, making up the entire contingent of judges appointed by Republican presidents.

Nobody at the Runnymede Society even dreams of that kind of success, at least partly because Canada’s political and judicial system probably makes it impossible. But the existence of Runnymede should theoretically make life easier for conservative politicians.

Consciously or not, through networking events and public debates, the Runnymede Society is helping build a roster of potential judicial appoints for any future Conservative government.

That’s no small thing. While a Liberal government is spoiled for choice when it reaches into the lower courts or academia for lawyers who share its view of the Charter, the pool has always been smaller for Conservatives.

By encouraging these “anti-establishment” ideas, the Runnymede Society is building a bench of lawyers and judges who may be more inclined to take an originalist view of the Charter or who may advocate for a more limited role for judges, or who may simply believe that the “living tree” is growing out of control and needs to be pared back.

“I think the more interesting project is exposing a body of students to the kinds of debates that are happening everywhere else in the world, but less so in Canadian law school classrooms, so that there is a diversity of views among future leaders of the legal profession, which I suppose includes judges, but that’s a 20-25 year project and not, I think, a conscious goal,” said Anglin, who was involved in judicial appointments during the latter years of the Harper government.

Kristopher Kinsinger, an Ontario lawyer and the national director of Runnymede, said the society’s commitment to the rule of law, fundamental freedoms, and the ideals of constitutionalism doesn’t necessarily make it a conservative group, but that those ideals should make conservatives feel at home.

“I don’t consider them to be inherently conservative principles, or exclusively conservative principles… but I think those commitments are necessary commitments for legal conservatism, but they’re not sufficient,” said Kinsinger.

“It’s no secret that legal conservatives want our society to succeed because they have a vested interest in seeing an organization where there is a robust commitment to those principles,” he said.