Only Theo Epstein can save the Toronto Maple Leafs
Even by their own confounding standards, the Toronto Maple Leafs are in a dizzying state of flux.
A dismal 2025-26 season saw decent expectations fizzle into a 36-loss debacle that confirmed a 59th straight year without the Stanley Cup.
Brad Treliving was fired as general manager, only for the Leafs – led by Keith Pelley, aloof parent company president – to bungle their search for a replacement.
John Chayka, the new general manager, has been out of the NHL since 2020, when he abruptly quit the same job with the Arizona Coyotes. Soon thereafter, Chayka received a year-long suspension for ‘conduct detrimental to the league and game,’ and was ostracised as a result.
Mats Sundin, meanwhile, has been mothballed since retiring as a player in 2009. The Leafs’ all-time franchise leader in points, Sundin is the new senior executive advisor to hockey operations – because, well, he once had lunch with Pelley and the pair hit it off, apparently. (1)
Such is the myopic chaos that plagues hockey’s most perplexing project.
Last Monday, the new administration assembled for an introductory press conference that was widely lampooned as a car crash. Infamously intense, Toronto reporters hammered the shellshocked triumvirate with simple questions that went unanswered, undermining the entire process.
“I have been in contact with about twenty people who work in the National Hockey League,” said Toronto Sun columnist Steve Simmons in an incendiary exchange with Pelley. “One was supportive of John’s hiring, and the other nineteen thought it was a sham, to be perfectly honest. Words were used like ‘con artist,’ ‘liar,’ and ‘salesman.’ How did you come to a different conclusion?” (2)
Crickets.
Barely seven hours later, though, disconsolate Leaf fans received an unlikely lifeline. How unlikely? Well, 8.5%, to be exact. That was the probability of Toronto winning the first overall pick in the 2026 NHL Draft Lottery. Remarkably, the Leafs did just that, freeing a path to select Gavin McKenna, hockey’s latest teenaged starlet, as a future cornerstone.
The emotional rollercoaster has exhausted even the most seasoned Leaf watchers, hardened by decades of incredulous decision-making amid sports’ most storied – if not its longest – active title drought. The notion of adding McKenna to Auston Matthews and William Nylander inspires hope and even excitement, but the new regime and its corporate overlords elicit mournful moans about enormous potential stifled by bureaucracy.
Through it all – the losses; the firings; Pelley using AI to suggest trades (3) – a Leafs Cup triumph still feels like a fanciful mirage. If anything, their chances of raising Lord Stanley’s chalice anytime soon have probably decreased in recent months. McKenna carries plenty of risk, while Matthews may soon follow Mitch Marner out of the door if the beleaguered hierarchy fails to convince him of a promising – or even cohesive – future.
Alas, possible solutions have dwindled to a scant few. Indeed, while watching the omnishambles unfold, it has struck me – rather flippantly, but also kinda seriously – that only one man can save the Toronto Maple Leafs. A man with a proven propensity to end fallow epochs in curse-addled fishbowls. A man driven by catharsis. A man who just gets it. Theo Nathaniel Epstein. The greatest sports executive of our age.
Epstein was Chayka once – or vice versa. Hired by his hometown Boston Red Sox in November 2002, the analytically inclined Epstein was, at 28, the youngest GM in baseball history. Chayka was two years younger, and held the same distinction in NHL lore, when the Coyotes appointed him as a fresh-faced wunderkind in 2016. There the comparisons end, however, because Chayka flamed out while Epstein carved a place in sporting immortality.
Theo’s exploits are, by now, well known; his achievements recalled instinctively by a populace that has seen his face in countless nostalgic documentaries. In 2004, Epstein led the Red Sox to their first World Series championship in 86 years. Three years later, he added a second title to the barren Fenway trophy case, before embarking on an even greater challenge with the Chicago Cubs, bereft of a crown since 1908.
Within five years, Epstein rebuilt the entire Cubs organisation – from the ballpark to the farm system, the analytics department to the dugout – into a formidable juggernaut. And when Chicago won the 2016 World Series, the Yale whiz had snapped 194 combined years of waiting in baseball’s two most famished cities.
Everything Epstein did with the Cubs – and, to a certain extent, with the Red Sox – is needed in Toronto with the Maple Leafs. Pardon the pun, but root and branch reform is required to exorcise whatever demons lurk in the Scotiabank Arena rafters and reconstruct a winning franchise in every facet.
Of course, the Leafs have attempted such reform – unsuccessfully – on multiple occasions. Most recently, The Shanaplan, a blueprint conceived by bulwark president Brendan Shanahan and executed – largely – by Kyle Dubas, his progressive protégé, yielded sustained contention coupled with crushing playoff profligacy. In 11 full seasons overseeing the Leafs, Shanahan delivered nine postseason berths – and just two playoff series wins against seven first hurdle exits.
Idealistic and comprehensive, The Shanaplan seemed expertly engineered to deliver a sustainable winner in Toronto – generational building blocks like Matthews, Marner and Nylander complemented by accomplished veterans en route to a long-awaited championship. Dubas even consulted Epstein’s Cubs while plotting a revolutionary course, visiting the team’s spring training facility in 2019, and the process seemed bound to reap rewards. (4)
For over a decade, indeed, the Leafs built critical mass, and at times, their momentum felt inexorable. Predestined, even. But in keeping with Leafs kismet, Shanahan’s teams always lost the season’s final game. Ultimately defeated, Shanahan left the Leafs last summer, and Pelley inserted himself – clumsily – into the void. If Shanahan could not break the curse, some wondered, could anyone in the hockey realm? Possibly not. Hence the theoretical flirtation with Theo.
Sure, somebody within the NHL could one day catch lightning in a bottle and win it all with the Maple Leafs. Stranger things have happened. Chayka and Sundin could even shock the world, from inauspicious beginnings. The consensus considers that unlikely, however, meaning the Leafs will probably seek another saviour in the medium term. And at that point, they must look further afield.
Theo Epstein is a baseball lifer, of course, and a pipedream transition to the NHL would invite incredible scrutiny. Nevertheless, top executives changing sports is not unprecedented. Paul DePodesta, another one-time prodigy, went from baseball (Oakland A’s) to football (Cleveland Browns) and back to baseball. He currently runs the Colorado Rockies, itself a thankless task, and has made a decent start modernising a moribund doormat. Maybe Epstein could follow suit.
In reality, though, that is highly unlikely. Despite the mesmerising potential and evocative poetry of such a notion, Theo Epstein will probably never be the Toronto Maple Leafs’ president of hockey operations. Why? Because Pelley would never think that far outside the box. And two, Theo has a pretty cushy life nowadays, free from the daily pressure cooker, making a return to the coalface optional rather than necessary.
Epstein left the Cubs in 2020 and enjoyed a successful stint with MLB, overseeing its acclaimed rules changes. He has since become nominally involved with various sports consortia, including Arctos and Fenway Sports Group – which, incidentally, owns the Pittsburgh Penguins, who hired Kyle Dubas as their lead executive in 2023.
At 52, two-and-a-half decades after he rose to prominence as baseball’s boyish messiah, Theo is probably content to put his feet up, watch his investments pay dividends, and occasionally dip in and out of light-touch consultancy. But if he ever wants one last dance – one last project, one last puzzle, one last mission impossible – where better than Toronto? The fairytale writes itself.
Sources
1. Friedman, Elliotte and Bukauskas, Kyle. 32 Thoughts podcast. [Online] May 4, 2026. https://podcasts.apple.com/au/podcast/a-conversation-with-chayka-and-sundin/id1332150124?i=1000766116342.
2. Keeley, Sean. Yahoo! Sports. [Online] May 6, 2026. https://sports.yahoo.com/articles/steve-simmons-explains-reasoning-around-010048905.html.
3. Siegel, Jonas, Johnston, Chris and Mirtle, James. The Athletic. [Online] April 15, 2026. https://www.nytimes.com/athletic/7194333/2026/04/15/maple-leafs-nhl-2025-26-dysfunction/.
4. Mooney, Patrick. The Athletic. [Online] April 8, 2019. https://www.nytimes.com/athletic/910387/2019/04/08/how-maple-leafs-gm-kyle-dubas-looked-to-the-cubs-for-innovation-while-chasing-the-stanley-cup/.