It starts with the math. You look at a spreadsheet, see a handful of high-performance assets, and convince yourself that the system is optimized. You stop building a team and start managing a portfolio. In Silicon Valley, we call this the "unicorn trap"—raising too much money, hiring too many mid-level directors with fancy titles, and forgetting how to actually ship a product that works under pressure.

In hockey, we call it being the Toronto Maple Leafs.

The Montreal Canadiens are currently in that dangerous, flirtatious stage of a rebuild where everything feels possible because nothing has been proven yet. They have the "vibes." They have a young core that hasn’t had its spirit crushed by a decade of early exits. But there is a rot creeping into the modern game, a desire to skip the hard labor of architecture and move straight into the interior design phase. If Montreal isn’t careful, they’re going to wake up in three years with a $90 million payroll and a roster that folds the moment the temperature in the rink drops below freezing.

Toronto is the ultimate cautionary tale of the analytics era. They are the NHL equivalent of a SaaS company that boasts incredible recurring revenue but hasn’t turned a profit since the Johnson administration. They’ve spent years paying four guys—the "Core Four," a term that sounds like a failed boy band or a McKinsey focus group—nearly half their total budget. It’s a top-heavy build that looks great on a PowerPoint slide. It wins games in October when nobody is hitting. But by May, when the game turns into a back-alley brawl, that expensive talent tends to vanish into the witness protection program.

Montreal is watching this. Or they should be.

The friction is already starting. You can feel it in the Bell Centre rafters. Management is trying to sell "the process," but the Montreal market has the patience of a toddler on a sugar crash. There’s a constant, low-frequency hum from the fanbase demanding a "big splash." They want a $10 million-a-year superstar. They want the flashy free agent who can put up 40 goals and sell a mountain of jerseys.

But look at the price tag. Look at the trade-off.

The moment you sign a Mitchell Marner-style contract—a deal that pays $10.9 million for elite regular-season production and a disappearing act in the playoffs—you’ve essentially locked your hardware. You’ve committed to a specific, rigid architecture. You lose the ability to pay for the grit, the depth, and the blue-collar defenders who actually win championships. You become a luxury brand in a sport that is, at its core, a demolition derby.

The Canadiens are currently playing a lean game. They’ve got Nick Suzuki and Cole Caufield on deals that look like bargains compared to the bloated spreadsheets in Ontario. They’ve got a pipeline of defensive prospects that represents real, tangible equity. This is the "bootstrapping" phase. It’s quiet. It’s disciplined. But the temptation to pivot is immense.

We’ve seen this movie before. A legacy brand gets tired of the "rebuilding" label and decides to buy a shortcut. They overpay for a veteran whose best years are in the rearview mirror. They trade away the future for a slightly better "now." Suddenly, you aren’t building a culture; you’re just managing technical debt.

The Leafs are the personification of technical debt. Every year they try to patch the code. They add a different veteran minimum defenseman or a "gritty" winger on a one-year deal, hoping to fix a fundamental flaw in the original build. It never works. The foundation is cracked because they prioritized individual stats over collective resilience. They built a team for the regular season algorithm, not for the human reality of the postseason.

Montreal has a choice. They can stay the course, endure the lean years, and build a roster that has layers. Or they can succumb to the vanity of the big market. They can start chasing the same high-priced, low-impact ghosts that have haunted Toronto since 1967.

The Bell Centre is a cathedral, but it’s one bad offseason away from becoming a showroom for overpriced mediocrity. Fans like to mock the Leafs for their failures, but the mockery should come with a shudder of recognition. The line between a "brilliant long-term plan" and a "permanent state of disappointment" is thinner than a skate blade.

If you spend all your money on the hood ornament, don't be surprised when the engine stalls out on the highway.

How much is a decade of "almost" worth to a city that measures success in parades?