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Why Did the Maple Leafs Sign a Contract Their Fans Hate?

Why Did the Maple Leafs Sign a Contract Their Fans Hate?

There’s a reaction that almost writes itself when the Toronto Maple Leafs sign a player like Darren Raddysh to a long-term deal into his thirties. On the surface, it looks like a mistake.

Toronto Maple Leafs News / Professor Press Box / June 21

Professor’s Cup of Coffee: Morning Thoughts on Listening to Matthews & Nylander

Back in early June, I wrote a post about something Auston Matthews and William Nylander said during their exit interviews. They talked about wanting more mobile, puck-moving defencemen.

Toronto Maple Leafs News / Yardbarker / June 20
Maple Leafs GM addresses Matthew Knies trade speculation

Maple Leafs GM John Chayka addresses Matthew Knies trade speculation

Toronto Maple Leafs general manager John Chayka delivered a reassuring message to fans regarding the trade speculation surrounding forward Matthew Knies.

Maple Leafs' move for Darren Raddysh is first big risk of NHL offseason
Three names Maple Leafs could still add to their blue line
Three-time Stanley Cup champion retires after 16-year NHL career
Red Wings want him back, but Patrick Kane has other plans
Brendan Gallagher situation: Canucks hoping for a sweet deal from Canadiens
Toronto Maple Leafs News / Maple Leafs Hotstove / June 20

Three points for Easton Cowan, more Artur Akhtyamov excellence completes the destiny: Toronto Marlies are Calder Cup champions!

“It’s awesome. It’s special. We couldn’t have done it without everyone who’s in this building right now. It’s something I’ll never forget. I’m going to soak this one in.

Jordan Staal News / Yardbarker Quizzes
The 'Conn Smythe Trophy winners' quiz

The 'Conn Smythe Trophy winners' quiz

The NHL began awarding the Conn Smythe Trophy to the most valuable player of the postseason beginning in the 1965 season. How many of the past winners can you name in six minutes?

The 'NHL Hart Trophy winners' quiz
The '5+ goal Stanley Cup Finals' quiz
The 'Playoff power play goal leaders by team' quiz
Toronto Maple Leafs News / The Hockey Writers / June 20
Marlies Just Won a Championship and Showed the Maple Leafs Something Important

Marlies Just Won a Championship and Showed the Maple Leafs Something Important

The Toronto Maple Leafs‘ American Hockey League (AHL) affiliate, the Toronto Marlies, weren’t supposed to be champions. But once again, they’ve reminded us that hockey rarely follows the script written for it in October.

NHL News / Yardbarker
The 25 greatest rookie seasons in NHL history

The 25 greatest rookie seasons in NHL history

There have been successful rookie seasons in NHL history, and there have been superior efforts worth celebrating time and time again. Here's our list of the 25 notable seasons from those with official rookie status, as deemed by the NHL, in reverse chronological order.

Darren Raddysh News / NHL Trade Talk / June 20
The Maple Leafs Bet Big on Darren Raddysh: Will It Pay Off?

The Maple Leafs Bet Big on Darren Raddysh: Will It Pay Off?

The Toronto Maple Leafs’ signing of Darren Raddysh makes a lot of sense once you look past the headline numbers. Raddysh didn’t explode overnight. He’s a late bloomer who kept getting better every year.

NHL News / The Hockey Writers / June 20
Three names Maple Leafs could still add to their blue line

Three names Maple Leafs could still add to their blue line

The Toronto Maple Leafs are making changes to their blue line. I

Maple Leafs' move for Darren Raddysh is first big risk of NHL offseason
Is Matthews Knies on his way out of Toronto?
The 'Highest paid NHL players in 2024-25' quiz
Auston Matthews News / Professor Press Box / June 20
The Maple Leafs' Biggest Offensive Addition?

The Maple Leafs' Biggest Offensive Addition?

When Auston Matthews scored 69 goals in the 2023-24 season, it felt like we were watching something special. Every night, there was a chance he'd do something nobody else in the NHL could do.

Toronto Maple Leafs News / Professor Press Box / June 20
The Marlies’ Lesson that the Maple Leafs Can’t Ignore

The Marlies’ Lesson that the Maple Leafs Can’t Ignore

Every once in a while, a championship team doesn’t really announce itself until it’s already holding the trophy. That’s what happened with the Toronto Marlies this season.

NHL News / NHL Trade Talk / June 20
Maple Leafs Were Never Really In on Oilers $74M D-Man — and Now Raddysh Makes it Official

Maple Leafs Were Never Really In on Oilers $74M D-Man — and Now Raddysh Makes it Official

The Darnell Nurse-to-Toronto hypothetical had everything a good NHL rumor needs — personal connections, a motivated seller in Edmonton, a new general manager looking to make his mark, and just enough links to the city to make it feel somewhat plausible.

Toronto Maple Leafs News / TheLeafsnation / June 20
Why the Maple Leafs should pursue Rūdolfs Bērzkalns with 3rd-round pick

Why the Maple Leafs should pursue Rūdolfs Bērzkalns with 3rd-round pick

While the Toronto Maple Leafs are looking to gain a franchise player with the first overall pick in the 2026 NHL Draft, the selections that follow are often the ones that can define a successful cohort or not.

Darren Raddysh News / Trade Talk Sports / June 20
Full Details of Darren Raddysh’s Maple Leafs Contract Revealed

Full Details of Darren Raddysh’s Maple Leafs Contract Revealed

The Toronto Maple Leafs coveted Darren Raddysh so much that they got ahead of everyone else to acquire him. After plenty of speculation connecting the

Toronto Maple Leafs News / The Hockey Writers / June 20
Maple Leafs News & Rumours: Matthews’ Bounce-Back & the Gamble Behind the Raddysh Deal

Maple Leafs News & Rumours: Matthews’ Bounce-Back & the Gamble Behind the Raddysh Deal

If you step back from everything going on right now, there are really only a couple of questions that matter more than the rest when it comes to the Toronto Maple Leafs’ immediate direction.

Toronto Maple Leafs News / 6IX ON ICE / June 20
Calder Cup Champions: Which Toronto Marlies prospects are close to NHL-ready?

Calder Cup Champions: Which Toronto Marlies prospects are close to NHL-ready?

The Toronto Marlies are the AHL’s Calder Cup champions after defeating the Chicago Wolves, the Carolina Hurricanes affiliate. For all the players involved, this is a valuable positive experience.

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The 'College World Series winners' quiz
 The 'College World Series winners' quiz
The 'NBA assist champions' quiz
 The 'NBA assist champions' quiz
The 'Game-winning-drives record by team' quiz
 The 'Game-winning-drives record by team' quiz
The 'Last cycle by MLB team' quiz
 The 'Last cycle by MLB team' quiz
Jim Hiller News / Athlon Sports / June 20
Maple Leafs' Jim Hiller Hire Brings Old Concerns Back Into Focus

Maple Leafs' Jim Hiller Hire Brings Old Concerns Back Into Focus

The Toronto Maple Leafs have turned to Jim Hiller to lead their latest reset, naming him the franchise's 41st head coach on June 17. The hiring follows a disastrous 2025-26 season that ended with Toronto missing the playoffs for the first time in a decade.

Toronto Maple Leafs News / Pro Hockey Rumors / June 20
Toronto Marlies Win 2026 Calder Cup

Toronto Marlies Win 2026 Calder Cup

The Toronto Marlies are champions of the AHL for the 2025-26 season, winning the Calder Cup last night. The Toronto Maple Leafs’ affiliate defeated the Chicago Wolves, affiliates of the Carolina Hurricanes, in a five-game Calder Cup Final series.

Toronto Maple Leafs News / The Hockey Writers / June 20
5 Options for Maple Leafs With 85th Pick in 2026 NHL Draft

5 Options for Maple Leafs With 85th Pick in 2026 NHL Draft

The Toronto Maple Leafs added some more draft capital to their cupboard for the 2026 NHL Draft after acquiring the Philadelphia Flyers’ 85th overall pick in the Emil Andrae trade.

Darren Raddysh News / NHL Trade Talk / June 20
Why the Maple Leafs Should’ve Seen Lightning’s Darren Raddysh Warning

Why the Maple Leafs Should’ve Seen Lightning’s Darren Raddysh Warning

The Darren Raddysh sign-and-trade between the Toronto Maple Leafs and Tampa Bay Lightning has its fair share of doubters from Toronto’s side. Signing a 30-year-old defenseman for eight years after one good season seems like a bit of a gamble, but the Maple Leafs had the cap space, and the hometown kid wanted to come home and play.

Artur Akhtyamov News / TheLeafsnation / June 20
Marlies’ Artur Akhtyamov named MVP of Calder Cup Playoffs

Marlies’ Artur Akhtyamov named MVP of Calder Cup Playoffs

Toronto Marlies goaltender Artur Akhtyamov was named MVP of the Calder Cup playoffs, winning the Jack A. Butterfield Trophy. Toronto captured its first Calder Cup since 2018, defeating the Chicago Wolves on Friday night.

Toronto Maple Leafs News / Daily Faceoff / June 20
Toronto Marlies win AHL’s Calder Cup for second time

Toronto Marlies win AHL’s Calder Cup for second time

One of the most surprising runs in American Hockey League history has been completed. Thanks to a 4-3 win over the Chicago Wolves in Game 5 of the Calder Cup Final, the Toronto Marlies clinched the franchise’s second AHL championship, taking home the trophy for the first time in eight years.

John Chayka News / Professor Press Box / June 20
Chayka’s Biggest Win? Messing with Other GM’s Heads

Chayka’s Biggest Win? Messing with Other GM’s Heads

The real move the Toronto Maple Leafs new general manager, John Chayka, pulled off isn’t a trade. It’s that he’s turned the NHL’s market upside-down by making other teams second‑guess everything.

Toronto Maple Leafs News / Inside The Rink / June 19

AHL Game Recap: Toronto Marlies Win Calder Cup

The Toronto Marlies and Chicago Wolves met tonight for game five of the Calder Cup Finals. The Wolves picked up an overtime win last night to force tonight’s game.

Toronto Maple Leafs News / TheLeafsnation / June 19
Toronto Marlies defeat Chicago Wolves to win Calder Cup for 1st time since 2018

Toronto Marlies defeat Chicago Wolves to win Calder Cup for 1st time since 2018

Easton Cowan registered three assists, as the Toronto Marlies defeated the Chicago Wolves 4-3 to win the Calder Cup. Toronto defeated Chicago four games to one, to capture the Calder Cup for the second time in franchise history, the first time since 2018.

Toronto Maple Leafs News / Daily Faceoff / June 19
Is Matthews Knies on his way out of Toronto?

Is Matthews Knies on his way out of Toronto?

New Toronto Maple Leafs general manager John Chayka has wasted no time putting his stamp on his new team, moving goalie Joseph Woll out to land a quality draft pick and defenseman Emil Andrae.

NHL News / Yardbarker / June 19
Maple Leafs' move for Darren Raddysh is first big risk of offseason

Maple Leafs' move for Darren Raddysh is first big risk of NHL offseason

The Toronto Maple Leafs are facing a massive offseason when it comes to the short-term and long-term outlook of their franchise. After shockingly missing

Leafs GM John Chayka speaks out amid Matthew Knies trade rumors
Three-time Stanley Cup champion retires after 16-year NHL career
Red Wings want him back, but Patrick Kane has other plans
Brendan Gallagher situation: Canucks hoping for a sweet deal from Canadiens
Former NHLer: Mike Babcock is 'only guy that has ever made me hate hockey'
Toronto Maple Leafs News / Daily Faceoff / June 19
Leafs GM John Chayka: Matthew Knies trade 'not probable'

Leafs GM John Chayka: Matthew Knies trade 'not probable'

John Chayka may not have been the most popular hire when he was named as the new general manager of the Toronto Maple Leafs, but he certainly hasn’t been shy about wheeling and dealing in the early days of his tenure.

There's considerable interest in Matthew Knies, and who else are the Leafs listening on?
Three Eastern Conference teams in need of major trades this offseason
Grading the NHL's recent head-coaching moves: Maple Leafs go off the board
NHL clears Mike Babcock to return to coaching, but it's still a bad idea for Oilers
The 'Highest paid NHL players in 2024-25' quiz

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