Is This a Once-in-a-Decade Buying Opportunity?

Are there any once-in-a-decade buying opportunities out there in a market that’s just a few good days away from hitting fresh all-time highs? Undoubtedly, the TSX Index seems to have more of a momentum edge over the likes of the S&P 500 and Nasdaq 100. After topping the U.S. markets in 2025, I certainly wouldn’t be surprised if the relative hot streak has room to run. Of course, there are risks to consider before backing up the truck on stocks that might have multiples on the higher end. Notably, the latest Canadian jobs number was not great.

And while it’s too early to tell if it’s an outlier or the start of a trend, I still think that investors betting on the retail trade should keep close watch on the consumer. While a weakening consumer could pave the way for more opportunities within the consumer discretionary space, I do think that investors should be ready to ride out what could a bit of a doozy in 2026.

At this juncture, though, I do see a few stocks that may very well be close to the cheapest they’ve been in a very long time. Of course, generationally-cheap multiples might not be indicative of more promising future performance. That said, if you’re looking for value where it can still be found, the following stock, I think, deserves a spot on your watchlist this spring.

Constellation Software used to be a market darling, but now it’s seriously oversold

Constellation Software (TSX:CSU) has suffered one of its biggest crashes in more than a decade, and while things have been looking up in the past month, with shares enjoying a relief rally of close to 13% in the timespan, the name remains a far cry away from where it once stood at just shy of $5,000 per share. Indeed, it felt like the software consolidator was bound for some sort of split. And while the share price is still quite hefty for a lot of retail investors at around $2,500 per share, you can now get two for the price of one compared to May 2025.

Whether that’s a good enough deal to buy after the AI-driven bloodbath in software stocks, though, remains the big question. For Constellation, the bad news keeps piling up. Whether we’re talking about the untimely departure of its top boss last year or the more-recent reckoning for software amid the release of new AI tools, Constellation could certainly use a bit of good news for a change.

The AI headwinds are overdone

Personally, I think the good news is that the stock has already priced in a more catastrophic scenario that might not be the most realistic. In my view, vibe coding and agents won’t render software platforms obsolete overnight!

Moreover, Constellation is in a good spot as it looks to help software companies make the pivot to become more AI-enabled. Moving ahead, look for Constellation to have more of a focus on AI-native software, as it does its best to spot great deals in a software scene that’s under pressure not seen outside of market-wide meltdowns. In my view, it’s cheaper to go bargain-hunting in software and as firms look to raise capital and talent for a “great AI pivot,” so to speak, Constellation’s role in all of this just got bigger.

Be careful when bottom-fishing

Just because CSU stock got hit with a 50% haircut doesn’t mean another one can’t happen, especially if there’s another software-selling spree ahead. If you don’t buy that AI will eat up all the software (even some of the AI leaders don’t think this), perhaps it’s time to give names like Constellation a closer look at these once-in-a-decade depths.

The post Is This a Once-in-a-Decade Buying Opportunity? appeared first on The Motley Fool Canada.

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Fool contributor Joey Frenette has no position in any of the stocks mentioned. The Motley Fool recommends Constellation Software. The Motley Fool has a disclosure policy.