The Toronto Maple Leafs have seen many changes to the organization over the last several months. The latest being the hire of new head coach Jim Hiller on Wednesday, and the acquisition of defenseman Darren Raddysh.
Hiller’s introduction to the Maple Leafs caps an abundance of decisions with the purpose of reshaping the organization. And Raddysh joining Toronto’s blueline is a big change to the team’s D-core.
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In other words, it’s the beginning of a new era for the Maple Leafs.
The start of this new era in Toronto began last off-season when Mitch Marner departed from the Maple Leafs in that sign-and-trade with the Vegas Golden Knights. But as the year went along, there were plenty more changes on the cards, and maybe some were not anticipated at the conclusion of the 2024-25 campaign.
Here are some of those notable changes and decisions that led to this new era for the Maple Leafs organization.
Joe Bowen’s Retirement
After being the voice of the Maple Leafs for over 3,800 games and over 40 years of broadcasting, Joe Bowen has just wrapped up his final year in the booth.
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It won’t be the same for Leafs fans with Bowen no longer behind the microphone. But the 75-year-old will be in retirement as a new era of Maple Leafs broadcasting begins, starting next season.
Joe Bowen Reacts To Tribute From Maple Leafs And Fans In Final Home Radio Broadcast Of Career
Joe Bowen Reacts To Tribute From Maple Leafs And Fans In Final Home Radio Broadcast Of Career Bowen will call his final Maple Leafs game live from the Canadian Tire Centre in Ottawa on Wednesday night.
Missing 2025-26 Playoffs
The Maple Leafs have been a perennial playoff team in the NHL. In fact, this past season was the first time Toronto missed the post-season in nine years.
Until last year, the Leafs have consistently made the playoffs since 2016-17. In other words, they’ve never missed out on the post-season in the Auston Matthews era.
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That change last season when Toronto ended their campaign as the last-place team in the Atlantic Division and fifth from the bottom of the entire NHL standings.
With that, the organization finds themself in a situation that it hasn’t experienced in a decade, marking a new timeline for the Leafs.
John Chayka And Mats Sundin Hiring
Following that disappointing 2025-26 campaign by the Maple Leafs, ownership believed it was time for a change in the front office.
Former GM Brad Treliving was fired in late March, and current GM John Chayka and senior executive advisor Mats Sundin were named the successors to the previous management.
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It was an interesting and unpredictable decision for MLSE to hire Chayka as the GM when he hadn’t been in the league since 2019-20. To add to that, they brought in Sundin, a former captain and icon of the Maple Leafs, but he never experienced a role in an NHL front office or in any league, for that matter.
This different approach and assignment of roles is something the Maple Leafs organization hasn’t gone through in recent years, and certainly marks a new era for the hockey club.
2026 First Overall Pick
In the aftermath of misery from the end of a poor regular season and the initial backlash from MLSE’s front office hires, Toronto’s spirits were reborn when they surprisingly won the 2026 NHL draft lottery.
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Toronto had the fifth-best odds and an 8.5 percent chance of winning the lottery, and with a little bit of fortune, that hope became a reality. It marks the first time the Leafs will get the first overall pick in a draft since they selected Matthews in the 2016 draft.
With the likelihood of taking left winger Gavin McKenna in this year’s draft, or even left winger Ivar Stenberg, Toronto is sure to get a talented youngster to boost a franchise that was trending downward at the end of the last campaign.
What Will Jim Hiller Bring To The Maple Leafs, What Could Make Him A Good Fit?
What Will Jim Hiller Bring To The Maple Leafs, What Could Make Him A Good Fit? Looking at Jim Hiller’s head coaching history with the Los Angeles Kings, what will he bring to the Toronto Maple Leafs, and what makes him a good fit?
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Jim Hiller Hiring
Hiller was another surprise hire by the Maple Leafs, both because of the lack of reports that included his name and also his previous tenure with the Los Angeles Kings.
Nonetheless, Hiller returns to the Maple Leafs after four years as an assistant coach from 2015-16 to 2018-19. And the word is, Toronto’s stars are a big fan of Hiller.
As an assistant, he ran the power play, and over the course of his Leafs tenure, he guided them to be a top-five power play. With someone like Matthews dropping in production over the years, maybe Hiller can bring the best out of him.
Additions To Blueline
The latest move Chayka has executed is a sign-and-trade with the Tampa Bay Lightning for Raddysh. They acquired him from the Bolts for a 2026 fifth-round pick, and then reportedly inked him to an eight-year extension worth $8.5 million per season.
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Raddysh, a Toronto native, was one of the top players in the 2026 UFA class, making this a big grab by the Leafs and a boost to their back end.
Maple Leafs And Lightning Finalize Sign-And-Trade For Top Pending Unrestricted Free Agent Defenseman Darren Raddysh At A Reported $68 Million
Maple Leafs And Lightning Finalize Sign-And-Trade For Top Pending Unrestricted Free Agent Defenseman Darren Raddysh At A Reported $68 Million Raddysh, who was projected as the top defenseman available on the open market in July, signed an eight-year deal reportedly worth a reported $8.5 million per year.
With that, throw in the trade with the Philadelphia Flyers when Toronto received 24-year-old defenseman Emil Andrae and sent away Simon Benoit. This improves the Leafs’ ability to advance the puck up the ice with Andrae’s puck skills, along with his ability to skate.
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Not to mention, the biggest change to Toronto’s back end may be yet to come. With talks of Morgan Rielly potentially being moved this summer, that would be the most era-changing move Toronto could make, considering he is actively the longest-tenured Maple Leaf on the team.
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