“Never interrupt your enemy when he is making a mistake,” ranks as one of Napoleon Bonaparte’s most famous quotes.

And it is one that a number of the politicians around Parliament Hill would do well to remember.

Last week, Liberal MP for Brampton East, Raj Grewal, announced he would be resigning his seat.

And just as the Liberal government was coping with an unwelcome and distracting event, rookie NDP leader Jagmeet Singh made a significant strategic mistake.

Singh, who has yet to find traction amongst many New Democrats — not to mention Canadians as a whole — has long been without a seat. His party, which has lost significant momentum from its 2011 high, when it obtained official opposition status for the first time, has been struggling.

The leadership contest to select Singh garnered little media attention. And since then, there have been few policy positions that the party has been able to call their own.

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Prime Minister Justin Trudeau has successfully positioned himself as the leader of the progressive movement, effectively overshadowing any attempts by the NDP to gain credibility on a host of issues. Even when the prime minister stakes out more conservative positions, such as with his vocal support for the development and construction of pipelines, the glow of progressivism doesn’t leave him.

Polling and byelection results reveal a party sputtering among voters. Polls have shown the NDP lagging far behind its rivals, and while many question the reliability of traditional political polling, the party’s results in byelections have done little to show them inaccurate.

Outside of Quebec, its results could at best be described as “middling” — and in Quebec, the epicentre of 2011’s success, the party is so far out of the game that it’s not difficult to imagine Quebec NDP MPs being a distant memory by 2020.

To make matters worse, NDP fundraising is at a recent low. The party, which has always struggled to effectively raise the money it needs to be competitive, has raised a fraction of what the Conservatives and Liberals have quarter after quarter since the last election.

The result? NDP MPs are voting with their feet: a significant chunk of the caucus have announced their plans to not run in the next election under Singh.

Not all of this, of course, is due to the fact their leader does not hold a seat. Similar struggles would not be solved by a place in the House of Commons alone.

But the fact the leader does not have a seat only serves to underscore these challenges, to make them more persuasive and to, more generally, lower morale for the caucus as a whole.

In an effort to combat a narrative that is not only developing but cementing, Singh announced he would run in a byelection in suburban British Columbia. It was a strange choice and an awkward fit: Singh had been an Ontario MPP and had little connection to Burnaby. What’s more, the seat is far from a safe one for his party.

Then, a gift appeared seemingly from nowhere: the Liberal MP who represented the very same seat in the House of Commons that Singh had represented in the Ontario Legislature, stepped down. In a byelection, Singh, a political celebrity in Brampton East and whose brother now represents the riding provincially, would have been a shoo-in.

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Inexplicably, Singh declined to take advantage of this near-sure bet and has stubbornly clung to his plan to take on a risky seat; a plan with plenty of downside.

It’s a decision that has long-standing New Democrats gritting their teeth. They wonder, rightly, why Singh is risking his entire political future on a riding that he has no connection to — with no real benefit.

Should Singh lose the byelection, it is almost certain that he will face a very unpleasant uprising. It will provide his internal opponents a tangible example of his lack of judgment and confirm the view he is ill-equipped to take on the Liberals in just over a year.

Jaime Watt is the executive chairman of Navigator Ltd. and a Conservative strategist. He is a freelance contributor for the Star. Follow him on Twitter: @jaimewatt

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