Cory Doctorow has given us one of the better words of the last few years: enshittification.

His 2025 book, Enshittification: Why Everything Suddenly Got Worse and What to Do About It, develops an argument he’s been making for years about how digital platforms evolve. Platforms begin by creating enormous value for users. Then, as users become dependent on them, some of that value gets shifted toward the businesses that need access to those users. Eventually, once both sides are sufficiently locked in, the platform starts clawing the value back for itself.

It’s a wonderfully rude word for a fairly sophisticated economic idea. And Uber is a useful place to start — because we should give Uber its due.

Calling a taxi used to be shit. You stood on a street corner and hoped one came past, or you called dispatch and were told one was ten minutes away, which could mean ten minutes, thirty minutes, or never. You needed cash. The driver needed to know where you were going. Depending on the city, getting into the business itself could require licences, medallions, affiliations, shifts, and a fairly serious commitment to making taxi driving your occupation.

Uber removed enormous amounts of friction. The customer suddenly knew where the car was. Payment disappeared into the background. The driver knew the destination. People with no interest in becoming conventional taxi drivers could turn a few spare hours into income — and that flexibility is worth something. Someone may quite rationally accept a lower hourly return in exchange for deciding they’ll work 6 to 9 on Thursday night, then not again until Sunday afternoon. That’s an economic benefit, even if it doesn’t show up neatly on a pay stub.

For a while, it was easy to see the gains flowing in several directions at once: passengers got convenience, drivers got access and flexibility, Uber got growth. Technology had created what I think of as an “efficiency dividend” — a bunch of things that had previously required time, labour, uncertainty, and infrastructure suddenly became much easier. That’s an extraordinary thing.

But it leads to a question I have been ruminating on: who should get the benefit of that efficiency? Not who does get it. Who should?

The person in the middle sees more

Uber’s current pricing structure makes that question particularly interesting. For riders, Uber uses upfront pricing influenced by distance, expected traffic, and real-time demand. For drivers in Canada, its upfront offers aren’t based solely on fixed per-minute and per-kilometre rates either — Uber says trip characteristics, market conditions, and demand at the destination can all affect the offer.

So the price the customer sees and the amount the driver ultimately receives aren’t simply two sides of one transparent equation. Uber sits between them, and the party in the middle knows a great deal. It can see where demand is, how much supply exists nearby, what types of trips are easy or hard to fulfil, what customers are accepting, and what drivers are accepting.

That doesn’t mean every dark theory about individualized pricing is true — Uber disputes the suggestion that it simply learns an individual driver’s desperation and keeps lowering that person’s pay until it finds their breaking point. But the larger structure is interesting enough without exaggerating it. The platform has better information than either participant. The passenger knows the price they’ve been offered. The driver knows the job they’ve been offered. The platform sees the marketplace. And whoever owns the marketplace occupies a rather useful position.

There are two prices hidden inside almost every transaction: the most the buyer will pay, and the least the supplier will accept. The economic opportunity lives in the space between them.

This isn’t unique to Uber. Amazon sits between sellers and buyers. Airbnb sits between hosts and guests. Food-delivery companies sit between restaurants, couriers, and hungry people who apparently cannot walk seven blocks for pad thai. Freelance marketplaces sit between companies looking for labour and people looking for work.

Sometimes the platform creates new competition for the worker, and wages rise. A brilliant designer in Halifax can suddenly sell to a sports club in Copenhagen; a specialist who once had three plausible employers may suddenly have three hundred potential customers. That’s good. But marketplaces can also create competition among workers. Put four thousand roughly interchangeable suppliers in front of the buyer, give the platform much better information than any individual participant, and the same technology can push compensation the other way.

The technology is neutral. The design of the market is not neutral.

We’ve seen this movie before

Sport has had its own intermediary for about as long as we’ve had scarce tickets. We used to call them “scalpers” — I’ve never particularly liked the word. Ticket broker, ticket speculator, reseller, whatever you call them, they existed long before Ticketmaster had a resale button.

In my early days at the Toronto Maple Leafs, we had season-ticket holders who were brokers themselves, and others who would effectively turn their books over to a broker. We had remarkably little visibility into how much of that was happening. Some of these were very legitimate businesses — they had offices, desks, assistants, telephones, customer lists. They knew who had four Leafs tickets available on Saturday night and who desperately wanted four Leafs tickets on Saturday night, and they connected the two.

It was very manual. It was also a real service. The broker had information the buyer didn’t have, and information the seller didn’t have. They carried inventory risk: if they bought or controlled a season-ticket book, they might do very well on a Saturday night against Montreal and considerably less well on an unattractive Tuesday in February. They had to balance the portfolio.

And then, as puck drop approached, there was another version of the market: the guy outside the arena, a fistful of tickets in his hand. “Tickets! Tickets for tonight!” At 7:25 PM, the economics became wonderfully uncomplicated - whatever those tickets had been worth at lunchtime, they were approaching zero. The market was clearing. Crude price discovery, between College subway and the front door of Maple Leaf Gardens.

Then the internet arrived. And here’s the thing that’s fascinating: technology should have killed the ticket broker. Instead, it turned the ticket broker into software.

When friction disappears but the intermediary doesn’t

Think about everything technology removed from that old transaction: no phone calls, no courier, no paper ticket, no assistant matching buyers with sellers, no physical handoff, no wondering whether the ticket was real, no meeting a stranger outside a bar. The modern platform can authenticate the ticket, list it, process payment, issue a new barcode, and deliver it to a buyer in seconds. Ticketmaster’s Canadian resale platform, for example, says listing is free but a seller fee is collected when the ticket sells; its resale purchasing terms also contemplate additional fees charged in connection with a purchase.

To be clear, those services have value. Authentication has value. Fraud prevention has value. Payments infrastructure has value. Customer service has value. A functioning marketplace has value. The point isn’t that the intermediary deserves nothing.

The interesting thing is what happened to the value created by the new technology, the “efficiency dividend”. The marginal effort required to move that ticket from one person to another has collapsed, yet the intermediary hasn’t disappeared — it’s arguably become more central. The broker once existed outside the team’s system. Now resale can live inside the same digital environment where the original ticket was issued. The same ticket can create an initial transaction and then another transaction on resale. And perhaps another. The inventory doesn’t change. The event doesn’t change. The underlying product doesn’t change. But there are more moments at which somebody can participate economically.

Again, this isn’t a screed about Ticketmaster. Ticketmaster has done something quite remarkable, in fact… it’s a legacy company from a pre-internet ticketing world that has successfully navigated enormous technological change without surrendering much of its position between event and customer. That deserves some respect. But it also makes Ticketmaster a perfect case study, because when technology dramatically reduces the friction in a transaction, we should probably ask: who should benefit from that reduction? The buyer? The seller? The team? The artist? The platform? Some combination?

There’s no law of nature that says the platform should capture all of it. There’s also no law of nature that says it shouldn’t. That’s a choice.

Before sports people get smug

This is the point where those of us in sports should resist climbing onto a pedestal, because we do versions of this ourselves.

I’ve spent a good part of my career in sponsorship, and I have absolutely charged two sponsors different amounts for what, on paper, may have looked like substantially similar inventory. A bank category might pay much more than a local retailer. Why? Because the category is worth more — the exclusivity is more valuable, the commercial outcome is potentially larger, the competitive pressure may be greater. A presenting partnership that can help a bank acquire thousands of customers isn’t necessarily worth the same amount as the same branding assets offered to a smaller business category. That’s not sinister. That’s value-based pricing.

And ticketing has always contained versions of this too. Centre ice costs more than the corner. Saturday costs more than Tuesday. A playoff game costs more than preseason. A suite costs more than a seat. The industry didn’t suddenly discover capitalism last Thursday, and charging different prices to different people or for different circumstances isn’t inherently wrong.

But I think there’s a distinction that’s becoming more important as our data gets better: are we pricing the value of the opportunity, or are we pricing the vulnerability of the buyer? Those are not the same thing.

Are we harvesting loyalty?

Professional sports teams know more about their supporters than at any point in history. Digital ticketing tells us who enters. Transfers tell us who passes tickets along. Resale tells us which games they choose not to attend and what the market may bear. Our systems can connect ticket purchases, merchandise, digital behaviour, food and beverage, premium purchases, and increasingly sophisticated engagement data. And AI is going to make us much better at interpreting all of it. That’s exciting.

I’ve argued many times that sports organizations have collected far more information about fans than they’ve learned to use intelligently. We digitized the ticket, but we didn’t necessarily modernize the relationship.

But there’s another side to that: what happens when we get really good at understanding the relationship?

Suppose I’ve been a season-ticket holder for 25 years. I attend 95% of the games. I renew immediately. I buy playoff tickets regardless of price. I take my kids. I buy merchandise. I complain occasionally but never leave. Your systems now have a very clear signal, and they could interpret it two ways:

Paul is incredibly loyal. We should reward him.
Or:

Paul is incredibly loyal. We can probably get another 10% out of him.

That’s where this shit gets uncomfortable. Because the second interpretation may produce a better short-term revenue result. The algorithm might be right. Maybe I will pay another 10%. Maybe I’ll pay another 10% next year too. Perhaps technology can eventually determine, with extraordinary precision, exactly how much pain my relationship with the club can absorb before I finally walk away.

Is that sophisticated revenue management? Or are we simply getting very good at harvesting loyalty?

What if loyalty accumulated value for the fan?

In the last twenty years we have designed loyalty programmes that largely accumulate value for the organization. Season-ticket tenure means predictable revenue, predictable attendance, lower acquisition cost, better forecasting, a reliable base for sponsors, a known audience for playoff sales, a committed advocate for the club. That supporter becomes more economically valuable to us over time.

But does the relationship become more economically valuable to them? Sometimes. They may get a scarf, a gift, a renewal event, a slightly earlier purchase window. Maybe their name goes on a wall after thirty years. Nice things. But the basic economics generally move in one direction: the loyal customer becomes easier to predict, and therefore easier to monetize.

What if we turned that around?

What if loyalty created stored value for the supporter — five years meaning one set of benefits, ten years another, twenty years another? Maybe the reward is a lower effective price, or protection from certain annual increases, or credits, or seat-upgrade priority, access to experiences, travel, hospitality, a meaningful right to buy scarce inventory. Some of these benefits might cost the club relatively little while carrying enormous perceived value for the fan — and that’s probably smarter than spreading a $40 loyalty saving across twenty home games, where nobody feels particularly rewarded.

The mechanism isn’t really the point. The principle is: what if our data got better at calculating what we owe loyal supporters, not merely what we can extract from them?

There are already signs of clubs experimenting around the edges of this idea. Some European football clubs have used attendance thresholds, resale requirements, and rebates to encourage season-ticket holders to actually use their seats rather than leave them empty. Fortuna Düsseldorf has gone even further, questioning the traditional assumption that ticket revenue must always sit at the centre of the model, using commercial partnerships to make selected home matches free to supporters under its “Fortuna für alle” initiative. These aren’t necessarily models everyone should copy, but I love what they do intellectually — they question the assumption that the relationship must always be club creates product, fan pays club, end of story. Because that isn’t actually how sport works.

Who creates the product?

Think about a football match with no crowd. Or hockey, or basketball. We don’t have to imagine it — we watched it during COVID. Same players, same rules, same rink, same court, same ball, same scoreboard, same television cameras. And something enormous was missing.

The crowd isn’t decoration. Atmosphere isn’t an incidental by-product. It’s part of what we’re selling. The supporter behind the goal singing for ninety minutes isn’t simply consuming atmosphere — they’re producing it. The season-ticket holder who renews before the first game provides working capital and certainty. The crowd makes the television product better. The crowd makes sponsorship more valuable. The crowd creates scarcity. The crowd builds rituals. The crowd tells stories. The crowd turns a football club from a company employing eleven people to kick a ball into something children inherit from their grandparents. And then we package all that emotion, history, noise, and belonging, and sell it back to them.

I’ve spent my career believing that professional sport creates communities. I still believe it. But perhaps we need to be more precise about the economic relationship: the club doesn’t create the community alone.

The community helps create the club.

We absolutely saw this with Major League Soccer in Toronto. The players are the product. The stadium is part of the product. The competition is the product. The game presentation is part of the product. And let’s stop pretending otherwise: the fans are part of the fucking product too.

Which means that when technology makes the ecosystem dramatically more efficient, perhaps they have a claim on some of that efficiency dividend. Not because sport should become a charity. Not because platforms shouldn’t make money. Not because dynamic pricing is inherently immoral. Not because every supporter deserves cheap tickets forever. But because healthy markets require some thought about where the value comes from in the first place.

If a platform removes friction, it deserves to benefit. If a club takes entrepreneurial risk, it deserves to benefit. If an athlete creates extraordinary demand, they deserve to benefit. And if supporters spend decades helping manufacture the scarcity, atmosphere, mythology, and cultural value that make the whole thing worth paying for? Maybe they shouldn’t always be the last people we think about when dividing the upside.

We’ve spent the last twenty years getting extraordinarily good at asking what a fan is worth to us. Maybe the next twenty should include another question: what are we worth to them — and what do we owe the people who keep showing up?

Loyalty shouldn’t be the easiest part of the relationship to exploit. It should be the most valuable part of the relationship to have.

On the night of March 24, 1996, a basketball game that meant absolutely nothing sent thirty-six thousand people into a delirium usually reserved for a championship. I remember it vividly. We thought we’d won it all!

The expansion Toronto Raptors — 17 and 49, in their very first (shortened) season, playing out the string in a cavernous domed stadium built for baseball — beat the Chicago Bulls. Not just any Bulls. Michael Jordan’s Bulls, who walked into SkyDome at 60 and 7, on their way to 72 and 10 and an NBA title, arguably the greatest team the sport had ever assembled. Final score: Toronto 109 – Bulls 108.

Damon Stoudamire, Mighty Mouse, went for 30 points and 11 assists and hit six threes. Jordan had 36. And it came down to the final possession, with Doug Christie draped over the greatest closer who ever lived, knowing - the way the whole building knew - that the ball was going to Jordan and there was nothing anyone could do about it. Christie contested. Jordan got a shot to the ri…

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I’d rather be debating Taylor Swift’s wedding (where are the pics??) or tracking (the world’s first former trillionaire) Elon Musk’s net worth. But the Substack gods — and football’s governing suits — have forced my hand.

When FIFA announced its latest scheme to consolidate and privatize its commercial operations, UEFA fired back with a line for the history books:

“It is not FIFA’s to sell. None of us are the owners of football.”

It’s a magnificent piece of rhetoric. It sounds like a romantic defense of the public commons against corporate enclosure — the village green protected from the private gatekeeper.

But UEFA desperately needs a mirror. Because while they preach civic stewardship from their lakefront headquarters in Nyon, they operate the exact same commercial monopoly they claim to despise.

The European Court of Justice saw right through the performance in 2023, explicitly ruling that UEFA held an unlawful monopoly and abused its dominant position to strangle competition. And whil…

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That’s the tell. A value that never forces a difficult choice isn’t a value. It’s décor.

So here’s a more direct test, taken from a small number of clubs that actually pass it: a value is real when it closes off an otherwise attractive option. You need to be seen to be living by your values, no matter the cost.

Run that test across professional sport and you find three genuinely different ways an organization can end up standing for something — and a fourth, much larger category of clubs that never decided at all, and got a reputation anyway.

1. In the Club Constitution: the belief is written into the operating rules

The strongest version of standing for something i…

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There is no point reading an organization’s stated values. None. A mission page, a code of conduct, the “values” section of an annual report — these documents are written to be read, not lived by. If you want to know what an organization actually believes, watch what it does when decisions come with consequences.

I know that claim sounds absolute, so let me complicate it slightly, because I’ve also been inside the process that produces these documents and it isn’t always cynical.

Early in my career, at the Raptors, the organization ran the standard exercise — an off-site meeting, a facilitator, lunch included — and it produced a vision and values statement. One of the outputs was a small card, one for every desk in the building. Plenty of people rolled their eyes at it, the way people reasonably do at laminated corporate form destined for a drawer. I asked our CEO about it once, half-expecting him to defend the process. He didn’t defend the card. He described what it was for. Paraphrasi…

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For six matches this June, BMO Field was “Toronto Stadium”. The world came.

Portugal fans filled the streetcars. Germans and Croatians shared bar tables. Ghanaian flags flew from car windows in Rexdale, Iranian ones in North York, Argentine ones on College. Kids are kicking balls in parks where I haven’t seen kids kick balls before. The city ran with a hum I’ve only felt a few times in my life — a version of Toronto entirely at ease with itself.

The tournament is still going, but Toronto’s part is over. This week, workers begin pulling out the temporary seats. FIFA branding comes down. In a few days, Toronto Stadium will be BMO Field again.

What stays?

I keep coming back to that question, because a few months ago, in the same city, a very different conversation began.

A System Coming Apart

This spring, the Future of Sport in Canada Commission released its final report, Transforming Sport in Canada: Time for Action, with 98 Calls to Action and a blunt conclusion. The Canad…

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The Commissioner of Major League Soccer takes the microphone first, with the face of a man unveiling a monument. Beside him sits James Johnson, who runs both Canadian Soccer Media and Entertainment and the Canadian Premier League, with the easy posture of someone delivering on a promise. Around them sit the owners of Toronto FC, the Vancouver Whitecaps, and CF Montréal.

Then comes the announcement, which on its face makes no sense at all.

The three Canadian clubs are leaving Major League Soccer to join the Canadian Premier League.

The Commissioner calls it the proudest act of stewardship in the league’s history. The clubs that carried MLS across the border when it needed them, he says, are coming home to anchor a first division built for Canadians, by Canadians. Their three places in MLS will be filled by new fra…

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