I missed the Pokémon craze when I was growing up and that’s a shame, because I missed out on an opportunity to watch this pastime evolve into a multi-billion dollar phenomenon. The trading cards alone, just a mere subsection of the Pokémon empire, are on track to become a $23.5 billion speculative market by 2030, and people are not being cool about it. The soaring values have led to a string of smash-and-grab robberies across the globe, totalling more than $500,000 in 2026 alone. With how expensive these cards can get (one recently sold for a six-figure sum), perhaps missing out on the hype was actually good for me and my wallet.

– Douglas Dunlop, Content Lead

The takeaway: The Dow was this week’s standout, with the rest posting modest gains, notable mainly because the old-economy index outperformed tech. On the individual stock side, Robinhood (NASDAQ:HOOD) dropped 13.5% this week after earnings showed its crypto revenue continuing to slide, a reminder that the crypto boom hangover is still very much in progress. Meanwhile, Intel (NASDAQ:INTC) jumped 12.8% — the stock had its best single day since 1987 last week, and it kept going this week. Everybody loves a comeback story.

Rogers Communications offered voluntary buyout packages this week to about about half (!) of its workforce as the company tries to cut costs after years of heavy spending. Their offer excludes unionized workers, on-air talent, Sportsnet staff, Blue Jays employees, and MLSE workers. This comes after Rogers' announcement last week that it's cutting spending on infrastructure and network investment by 30% this year, pointing to a difficult regulatory environment and highlighting that its subscriber growth has slowed. According to The Globe and Mail, Rogers has $34.7-billion in long-term debt on its books, and they’re apparently turning the stadium seats upside down, looking for change.

This may look like just a Rogers story, but it’s bigger than that. Bell and Telus have been cutting jobs for the last two years, and all three of the major telecom companies are dealing with the same problem: they borrowed against expected subscriber growth, but price competition from carriers like Freedom Mobile and cuts to immigration threw a wrench in their plans. What’ll matter more is how many of Rogers’ employees actually take the buyout – Shaw made a similar offer in 2018, and five times (!!) as many of its workers took the deal than expected.

by Anthony Milton

This is an excerpt of an article originally run in full on The Margin.

In 2021, the federal government gave provinces the green light to legalize online gambling without clarifying one basic question: when do your winnings become taxable? Five years later, the answer is still being decided case-by-case in court, as millions of Canadians now bet regularly online.

Ontario was the first province to allow DraftKings, Fanduel, BetMGM, and other big gambling companies to set up shop in 2022. That created a $1.2 billion industry overnight: in the first year, 1.6 million accounts wagered $35.5 billion. It also had dire consequences: calls to help lines tripled, gambling-related bankruptcies quadrupled, and the number of Ontarians struggling with problem gambling jumped to 11% (up from just 1% in 2018).

Meanwhile, courts were making another mess: deciding that some gambling winnings are taxable, while previous cases had already ruled the opposite, creating a contradiction for gamblers and legal experts alike. Parliament legalized gambling without settling on the tax rules, and it needs to fix that before more Canadians stumble into the same confusion.

Take the case of Fournier-Giguère et al. v. Canada, which dealt with three professional poker players in Quebec and came to a close in 2025. The trio had done well for themselves, with each winning hundreds of thousands of dollars in poker tournaments annually – one even managed to score nearly $2 million in a single year.

So it came as an unwelcome surprise when the taxman came for a significant chunk of their cash. Traditionally, a gambler’s winnings weren’t considered taxable at all; for one thing, gambling is generally considered to be a hobby, and for another, gamblers tend to lose rather than win. The three poker players fought back, arguing that the tax code specifically exempted money gained or lost from “a chance to win a prize or bet.” In the end, the court disagreed: their gambling, it said, was so professional that it constituted a business, and business income is taxable. Pay up, said The Man.

Read more

Douglas Dunlop, Content Lead: I recently became enthralled by a 40-minute video about digging holes. Let me explain: the video, by YouTuber Jacob Geller, starts with a simple observation – people love digging holes, especially guys at the beach – but he argues that the inanity of this topic reveals something deep about our human psyche. Why do we as humans do the things we do? This "silly" video about digging holes (and yes, he and his friends do go on a hole-digging trip) ended up making me feel awed – humanity’s unbridled curiosity for the unknown pushes us beyond our comfort zone, and I love it.

My awed feeling isn't unusual after consuming Geller's videos – his work always makes my brain perk up in a surprising way. His Fear of Dark video, for instance, argues that darkness is not just an absence of light, but a possibility; something is there, or something is not, and that’s what trips us all up. Geller's work stays with you in the best way, no matter how deep or dark the subject matter might be.

From The Margin group chat:

Last week, we forgot to ask you a question at all! Oops oops oops. Here are some of our favourite responses:

Brilliant stuff.

This week, we’re actually remembering to ask you something, and we want to know: What’s the best piece of advice you’ve received from a boss?

Send your responses to [email protected] by next Thursday, May 7 at 12 p.m. ET and we might feature it in next week's issue.

If you liked this newsletter, hated this newsletter, or are totally indifferent to it, hit the reply button and tell us why! We’re so lonely.

This week’s contributors: Anthony Milton (writer), Tyler Haw (audience engagement), Douglas Dunlop (content lead), Jenna Zaitchik (senior creative designer), Shazia Khan (social media strategy manager), Kat Angus (deputy editor), and Eric Wainwright (editor in chief).

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