'I want to invest where the puck is going': Kevin O'Leary calls the Canada-US tariff chaos a "ridiculously fantastic" buying opportunity

Using an analogy steeped in Canadiana, O’Leary said, “I don’t want to invest where the puck is, I want to invest where the puck is going,” while also noting how “Carney cannot sustain 50% tariffs on the Canadian economy. That will put the country into a recession and he knows it. And I don’t think 26 states in the US can sustain 50% tariffs with their biggest trading partner, and Trump knows that.”

He closed off the post by stating: “this is a politically motivated period of time, I would call it 60, 90 days, where you can invest in a country in economic chaos at the bottom and get a ridiculously fantastic return over the next five years.”

It’s a bold call, and it’s landing at a tense moment. The US hit Canada with 50% tariffs on roughly US$28 billion of exports on August 22, after trade talks with the Trump administration collapsed. Prime Minister Mark Carney is set to respond in kind on September 8, applying duties of up to 50% on more than 700 US products, from steel and dairy to smartphones and furniture.

For everyday Canadian investors watching their RRSP or TFSA balances move with every trade headline, the question is simple: should you act on a call like this?

What is O’Leary actually predicting?

O’Leary isn’t recommending a specific stock or fund. He’s making a macro call: that political and economic pressure will force a resolution within a few months, and that buying Canadian assets now — while sentiment is at its worst — could deliver a fantastic return over the next five years.

That’s a classic contrarian trade: buy fear, sell euphoria. It has worked for some investors in past downturns. But it depends on getting both the timing and the direction right, twice — once on entry, and again on knowing when the chaos has actually passed.

Why the 60-to-90-day window is riskier than it sounds

Trade policy hasn’t moved as fast as O’Leary’s timeline assumes. Trump’s 50% tariff threat on Canadian autos, trucks and steel was deferred, not cancelled, and won’t be revisited until January 2027, per Investing.com. Negotiators had already blown through one deadline this summer before the current tariffs took effect, NBC News found. A resolution in 60 to 90 days is possible, but nothing in the recent record suggests it’s likely on that timeline.

What the market data actually shows

Canadian stocks have been more resilient than the tariff headlines suggest. The S&P/TSX Composite has gained more than 50% including dividends since the start of 2025. Furthermore, analysts at Edward Jones describe the new tariffs as a meaningful but manageable headwind rather than a recession trigger, since the industries most exposed represent a small share of the index.

However, not everyone agrees the market is cheap. A Reuters poll of equity strategists and portfolio managers conducted in mid-to-late August found 11 of 14 respondents predicting that a correction was likely or very likely within the next three months. IG Wealth Management’s Philip Petursson pointed to above-average valuations, rising long-term US bond yields, weak seasonality and the US midterms as reasons for the elevated risk. Lorne Steinberg of Lorne Steinberg Wealth Management called bank-stock valuations “stretched” and said the sector could be flat for the next 12 to 18 months. In other words, the bottom O’Leary describes isn’t something the market has agreed on.

How should Canadians actually respond?

For most Canadians, the smarter move isn’t timing a single 90-day trade — it’s using the volatility as a reason to check the basics.

• Stick to a plan, not a headline. Regular RRSP or TFSA contributions on a set schedule reduce the risk of getting the entry point wrong, which matters more than getting the thesis right.
• Diversify across sectors and borders. Tariffs hit specific industries hardest, so a portfolio concentrated in steel, autos, dairy or furniture carries more political risk than a broadly diversified one.
• Treat hot takes as one input, not a signal. O’Leary’s own hypothesis depends on a political timeline no individual investor controls.

Canadians with cash on the sidelines and a long time horizon may reasonably see this volatility as a chance to top up existing positions. Those closer to retirement, or without room to ride out a longer trade war, have less margin of error for a bet that depends on a 60- to 90-day deadline holding.

The bottom line

O’Leary’s instinct — that fear creates opportunity — isn’t wrong on principle. Turning it into a personal investing decision means separating the macro story from your own timeline, risk tolerance and existing exposure to the sectors this trade war is hitting hardest. That’s a decision worth making with a plan, not a deadline borrowed from a TV investor’s social media post.