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Prime Minister Stephen Harper participates in a question and answer session with the Greater Kitchener Waterloo and the Cambridge Chambers of Commerce in Kitchener, Ont., on Friday, April 25, 2014.The Canadian Press

Prime Minister Stephen Harper's guiding philosophy of governing without worrying about activist judges has run smack into the Supreme Court of Canada.

Five overwhelming losses in little more than a month, all of them in areas dear to the Conservative government's heart, leave Mr. Harper with a tough choice: Make a political issue of being opposed by unelected judges or modify his agenda (and perhaps his governing style) so it will pass legal muster.

In all five cases, including Senate reform on Friday, three tough-on-crime laws and even Mr. Harper's choice for a Supreme Court judge, only one supportive voice was raised on the court, and just once. And this from a court whose eight members include five appointed by Mr. Harper.

It has been a rapid-fire education in the limits of government action – or a comeuppance – with few parallels in Canadian history, some legal observers say.

Mr. Harper's losing streak "highlights a judicial-legislative clash in ways that have not been highlighted in the recent past, and perhaps ever," Wayne MacKay, a constitutional specialist at Dalhousie University's law school in Halifax, said in an interview.

The cases amount to a test of Mr. Harper's long-held views on the proper relationship between elected politicians and appointed judges. Ten years ago, when Mr. Harper was in opposition, the man who went on to be his first justice minister described how legislators had allowed unelected judges to deprive them of their self-confidence.

"The Charter of Rights has brought about a mindset, a culture or a way of thinking among legislators that in practical terms limits the democratic institutions to act proactively or indeed to react to serious situations," Vic Toews told a pro-life conference in Winnipeg.

That speech points to Mr. Harper's more aggressive mindset. His own public criticisms of judicial activism convey the view that the Supreme Court has wrongly asserted its supremacy over Parliament, and should be challenged on it.

Dennis Baker, a political scientist at the University of Guelph, said Mr. Harper's views are not disrespectful of the Supreme Court. "It's being aggressive about Parliament's ability to make laws. Sometimes that means pushing up against constitutional boundaries. There has been no instance of the government defying a court or not accepting a decision."

Others, such as Prof. MacKay, cast Mr. Harper's views in a negative light.

"My personal, obviously biased view [as a law professor] is he doesn't adequately respect and value the role of the courts in a checks and balances system. It's almost a kind of arrogance. 'I know what is best; I'm acting on behalf of the people of Canada and therefore, why should unelected, appointed bodies be able to block my vision of what is best for Canada?' "

Either way, though, what unites all five cases in the Harper losing streak is that "there are certain limits that you cannot cross, because we have a Constitution within which you must operate," Prof. MacKay said.

The court that has handed such stinging defeats to Mr. Harper is hardly a bunch of activists. Mr. Harper has mostly appointed conservative jurists whose tendency is to defer to government, such as Justices Marshall Rothstein, Michael Moldaver and Richard Wagner. "I don't think any of these cases indicate an activist judiciary," said Joel Bakan, a professor at the University of British Columbia's law school.

"The decisions are not at all controversial when you look at them from a legal perspective. What they indicate is a government that has overreached in its power. The Harper government has gone after some very ancient and rooted common-law protections." In one case, the government imposed retroactive limits on parole. In another, judicial discretion over sentencing was constrained. In a third, habeas corpus, the right of prisoners to go before a judge and protest against the conditions of their confinement, was restricted.

The question for Mr. Harper is where to go next, as his policy agenda runs aground. He could become more conciliatory, as in last week's climb down on the proposed Fair Elections Act, which might ultimately have been challenged at the Supreme Court. Or he could make the Supreme Court's rejection of his policies a political issue.

But that, too, seems not to be a winning strategy, said Roger Gibbins, senior fellow at the Canada West Foundation, a think tank focused on the West.

The Conservative government could "run against the Supreme Court in the next election," he said, but "it's not clear that this is a wedge issue" because no single issue is truly a flashpoint between the public and the court.

The losing streak "reinforces a public perception that this is a government that is not consultative, that tends to stake out a position and bull ahead on it," Dr. Gibbins said.

Chief Justice Beverley McLachlin speaks of a "dialogue" between Parliament and the judiciary, but the five cases appear to leave little room for a government reply. On Senate reform, for instance, Ottawa has no appetite for opening constitutional talks with the provinces. (Perhaps most Canadians share that reluctance.) On sentencing, where the Supreme Court urged the federal government to be open about what it is trying to do, it may be hard to address the principle of proportionality without receiving another rebuke from the judiciary. The cases may prove more dead end than dialogue.