The Leafs ... 2026/27 ... a MIllion Questions.

Please Note:

The following is really only for Leaf fans. If you think it's worthy, please pass it on to other members of Leaf Nation.

It's very long (some would say a 3-beer read) and will take time if you decide to proceed. 

I wrote it in bits and pieces while waiting for Leafs off-season news to develop ... and I was holding out to see where Patrick Kane would land (do you think he would have helped Matthews?) and, of course, what about Morgan Rielly?

You might say that I have a million questions ...

No interest? Fair warning ...

HIT DELETE...

Toronto Maple Leaf Hockey Club

Opening Night of the regular 2026 - 2027 season

September 29, 2026 - vs - The Montreal Canadiens

It's been 59 years since the Toronto Maple Leafs won the Stanley Cup. 

That's long enough for men to walk on the moon ... long enough for hockey to arrive in the desert and, apparently, long enough for Florida to become a better hockey territory than Ontario. Tampa won two -- Sunrise won two ... Vegas arrived late to the party and still managed to win before Toronto. Could anyone ever have predicted this back in 1967?

As Leaf Nation 2026-27 embarks on another quest for the Silver Chalice and the team begins retooling, I have a bunch of oddball QUESTIONS -- that appear in no particular order.

But first, let's start at the beginning, and say the beginning is that day in June/2026 when MLSE's Keith Pelley conducted the long-awaited press conference that launched the careers of the new Leafs GM and former team captain, Mats Sundin. 

Pelley stepped to the microphone, Leaf Nation waited, pens were poised, tape recorders charged, TV cameras blinked ... this was supposed to be the beginning of a brand new hockey era in Toronto. 

So naturally, he started by talking about the Raptors and their loss the night before. Sometimes life writes comedy better than the comedians.

Then, he used his close-up magic skills -- a Vegas magician would have been envious -- to skip over the questions posed by Steve Simmonds, the Toronto Sun hockey writer, who gave the results of his poll of 20 NHL executives on the choice of the new Leaf GM. 

His survey found only one supporter for the new man, John Chayka. According to the other 19 questioned, Simmonds claims, "The hockey world is astounded by your decision to hire Chayka, and they used words like con artist, liar, salesman and a sham to describe him." 

July 27/2026 we found out more. The hiring process was filtered through Neil Glasberg, president of PBI Sports, who claimed: "It was an incredible exercise that we went through ... we exhausted the universe of candidates."

In my opinion, all eyes will be on his selection and the "incredible" process. If Chayka proves to be the person as described by Simmonds' informants, it may mean the demise of Glasberg's headhunter business.

QUESTION: Are you suspicious when someone uses the adjective "incredible" when they try to tell you about their effort?

QUESTION: It's understood that every member of Leaf Nation has great respect for Mats Sundin and his outstanding playing career in Toronto. But he's been living about as far away from the NHL as you can get, and, in the NHL of 2026, in my opinion, Leaf/NHL hockey-wise, he knows nothing about anything. As a 55-year-old veteran player, how is he expected to get the attention of today's young NHLers? His resume means nothing to them because most of them have never heard of him. Can we agree ... great players don't automatically become great executives (Howe, Bobby Clarke, Rocket, etc.)

Incidentally, last season, there were 45 NHL players aged 20 or younger.

Fun Fact: Mats and John Chayka had a 5-hour session with Leaf coach Craig Berube and picked his brain. Then, 4 days later, released him from his contract that had 2 years remaining. The coach incorrectly thought the meeting was a good first step in getting the team back onside ... he didn't realize it was his exit interview.

QUESTION: Do you think Chayka/Sundin asked any of the current players for an evaluation of their coach before they gave him the pink slip?

QUESTION: Why did Chayka get rid of their salary cap guru, Brandon Pridham and the assistant, Clancey, just when it looked like their history with the club and expertise with the collective bargaining agreement may be of most value?

QUESTION: A pre-season observation ... "When will Chayka do something positive for this team" 

ANSWER: He finally did! 

Moving Marlies Calder Cup-winning coach John Gruden up to the big club as an assistant coach AND appointing Steve Sullivan coach of the Marlies (he'll be a coach who doesn't ignore "little players with talent" because he was one himself) AND announcing former Leaf hard rock Mark Giardano as Sullivan's assistant ... it's genius! And, the additional appointment of Patrick O'Sullivan as Director of NHL Player Development, in August, is a Leaf home run for me ... his influence on and off the ice will be something you can't buy.  

Then, he dumped Haley Wickenheiser. Dumb.

But back to Mats ... 

QUESTION: From his job title, does anyone know what Mats is responsible for? As of July 15/2026, his duties do not include Director of Player Personnel; that post went to longtime Sabres executive Jeremiah Crowe.

QUESTION: When Sundin has to face the press corps following a Leaf loss this October, he, not Matthews or Tavares or Reilly, will be asked to explain.  He'll be comfortable with his gaggle of former press pals. But, a few weeks into the season, if things don't improve on the ice, the press will set aside the buddy/buddy approach with Mats and start to fire off some hardball questions that he won't be able to answer. Once that happens, will Mats become as scarce as Shanahan was for the 10 years when the team didn't execute the "Shanny Plan?

But, back to Neil Glasberg ... Mats might not be on the mat for this. According to Glasberg, "It's a tough market to be in, as everyone knows the media is diligent and there is a lot of answering to the media", and he admitted: "Chayka was a great fit in that sense". Ya, we'll see about that.

But, back to what Simmonds was saying about his survey of "Hockey People" who claim Chayka is a "con artist, liar, salesman and sham" ... Toronto media has been alerted and will most definitely be up to the challenge. Upcoming Simmonds & Chayka interviews should be interesting.

QUESTION: What does Mats know about Leafs' talent in the system? What does he know about the day-to-day business side of making decisions for an NHL club and being able to stickhandle around the salary cap? What does he know about the collective bargaining agreement from the business side of the desk?

Marner is gone. His move to Vegas was a tragic loss for the Leafs -- they missed the playoffs for the first time in 9 years. In my opinion, he made everybody he played with play better. But there are always two sides to every tragedy, and I won't use this space to take sides. I wanted to see where he landed by season's end. The result was spectacular for him and the Golden Knights and not so good for Leaf Nation. As you may know, he led all 2026 playoff players in points. 

QUESTION: Would you like to know what former coach Berube thought of Marner? This is from an on-air interview, July 9/2026 ... "I thought we lost our emotional leader, for sure," Berube said. "It was a big loss, not only the player, but in the locker room, on the bench, in practices, things like that. I thought that he brought that element. I thought he held guys accountable."

QUESTION: Why did the Leafs trade Fraser Minton to the Boston Bruins along with Toronto's 1st-round draft pick for Brandon Carlo (Minton scored a very respectable 17 goals and 18 assists for the past season)?

The new management finally admitted that the former suits made a mistake with Carlo and dumped him, but why did they trade away Simon Benoit, who actually used his size and played every game with a "little sandpaper"? 

Incidentally, in return for Benoit and Holl, we received two players who should fit nicely into the "Marlies lineup".

Keep in mind the Leafs' defence in the 2025 - 26 campaign was the second worst in the NHL with a 3.60 goals-against average.

Questionable defence ... Not many good things are said about Morgan Rielly and the way he plays his position. Like Carlo, he seldom touched anyone and admitted, with an open apology, to his lack of pushback with Gudas on the Matthews' season-ending hit. I think he's a gifted skater and a solid passer.

QUESTION: A blog reader (Slatts) asks: What would he look like as a 3rd or 4th line center -- his skill set reminds me of former Leaf, "Red" Kelly. When "Red" joined the Leafs as a 4-time Stanley Cup-winning defenceman, they moved him to centre, and he went on to earn 4 more Cups.

This year's training camp will include lots of arithmetic. 

Entering this season, the Leafs are over the $104 million salary cap.

Domi, Cowan,  Josuha, and Lorenz scored a total of 40 goals last season -- Bobby McMann actually had a very respectable 19 goals, but they shipped him to Seattle before the end of the season. 

QUESTION: Do you think this group of four is the nucleus for a very good American League team?

QUESTION: I asked a dozen hockey buddies ... "When Matthews scored 69 goals, how many were assisted by Marner?" They guessed between 20% and 40%. The actual answer was 57 assists to Matthews' 69 Goals -- or 82.6%. To start the 2025 - 26 season without Marner, the Rocket Richard Trophy winner, Matthews had the talents of Max Domi to replace Marner on his wing -- (FYI - Domi had scored 29 goals in the last 3 years with the Leafs.) 

Matthews finished the 2026 season with 27 goals. -- without Marner.

In his last year as a Leaf, Marner had 102 pts.

QUESTION: Back to Mats ... If the Leafs were going to select a former player and give him a mystery title, why not select a terrifically popular former captain who's loved by Leaf Nation and knows today's game and its players?  Why wouldn't they select Wendel or Sittler, who are already on the Leafs' payroll as team ambassadors? Or, what about Gilmour, who coached the Kingston Frontenacs for 3 years and knows all about the ins and outs of the OHA ... they didn't call him "killer" for nothin'.

Pelley chose to ignore hiring these possible candidates, hired Glasberg to make the selection for him, and went for a former captain who moved on from the Leafs to Vancouver at the end of his career, and we got nothing for him. 

And, the recent announcement cost the Leafs a huge bag of money for uprooting his family and setting him up in Leaf Land ... MLSE doesn't really care about this expenditure ... they have lots more money on the way. To prove it, I'll describe a disgusting Leaf money maker a little later in this essay.

But first, another QUESTION: On July 8/26, the Leafs hired former Senators assistant coach Daniel Alfredsson as the #2 man behind the Leafs bench (his actual title is "Associate Coach," not "assistant coach," whatever that means). When asked, "Why were you interested in the Leaf job?" Alfredsson replied, "I want to expand my experience as an NHL coach". So he's using the Leaf job as a stepping stone to greater things? Not a bad strategy ... John Tortorella has been around forever but only won one Cup with Tampa 22 years ago and has parlayed that into head coach jobs with 5 NHL clubs.  

I have to ask... weren't former fan-favourite Leaf captains Clarke, Sittler, or Gilmour available? But maybe the answer is right in front of me ... this troika are super competitive professional athletes -- it's in their DNA. They've already seen the inner workings of the PELLEY run organization and, for now, are happy to get paid and stay on the bench during Glasberg's "incredible" search.

The Leafs have a sad history of General Managers: Gord Stellick, John Ferguson, Brian Burke, Dubas and Treliving. And the team's last president gave $50 million to Babcock -- who got a cheque for $30 million just to show up on the first day of his job.

A reaching back QUESTION: If Shanny gave his coach $50 million, did he, as president, get paid $50 million + 1 dollar? 

QUESTION: Why did Shanny choose to boot legendary manager Lou Lamoriello from his staff and keep Dubas, who would later insult him, the team and the city? Incidentally, Lamoriello is the only manager to earn the title Manager of the Year back-to-back. And Dubas may not be finished smacking the Leafs organization ... On July 15, 2026, he hired the aforementioned Brandon Pridham, who was the Leafs' former Sr. Executive responsible for contract and cap management. Then, Dubas grabbed forward Nick Robertson. Like him or not, in the past 3 years, he scored 45 goals in 203 games, vs. teammate Max Domi, who managed only 29 goals in 234 games for the same 3 years. 

QUESTION: Will Leaf fans be wondering "why'd we let him go" if he goes on to have a stellar career as a Penguin when he gets more than 11 minutes of ice time per game that the Leafs gave him? 

Gawd, I hope Dubas doesn't succeed.

QUESTION: What about Matthew Knies? I cringed with the news that the new Leaf GM was actually shopping him during the summer and came close to a deal with the Habs. Can you imagine his talent wearing the Bleu-Blanc-Rouge playing on a line with Suzuki or Caufield? Do you like Knies? I do. He scored 29 goals in '25 and 23 goals in '26 -- that's respectable -- a player who can score 20 is a player. He's got a nice upside. I want him in Blue and White to retirement. But, as a young 20-something, he just learned a valuable lesson ... he's not a Leaf ... he's just a moveable part in a business. A secondary QUESTION: ... depending on his maturity, he now knows the organization doesn't love him. Will he go into a scoring shell this season or be lights-out scoring 35 this year and improving his resume for his next contract?

QUESTION: The lack of investment in the Leaf franchise began years ago with "Pal Hal" Ballard, and his refusal to keep fan favourite, and team captain Dave Keon, who drifted to the WHA just so he could get a pay raise, even though Ballard claimed Leaf seats had been sold out since 1946 and he asked Molson's for a million dollars to take ownership of all the advertising signage space in the Gardens -- the year was 1975. 

If Ballard had been thoughtful and considerate of the Toronto fans and a leader whose goal was to bring a championship to our city and Leaf Nation, wouldn't we now be praising him as a sports hero? Years after his passing, wouldn't we talk of him as a champion for our city, which many hockey fans consider to be the centre of the hockey universe?

Instead, his name reminds us of a big, brash, blowhard who was only in it for the money -- with one exception -- he gave us Borje Salming for 16 years. 

Ballard's successor in 1996, Steve Stavro, the grocery store magnate, had a chance to bring Gretzky to the Leafs through the work of the best Leaf GM, Cliff Fletcher, who was "giddy" at the prospect of having #99 suit up with Sundin and Gilmour. Stavro didn't agree to the deal for Gretz because he claimed, "Where would I get the money to pay him? "I can't add seats, and all the signage and radio/TV contracts are already sold out."

Since I mentioned the faulty Leaf ownership, please pardon me for stickhandling around to a Maple Leaf sidebar. 

 As a hockey fan, I've always been impressed with the way the Montreal Canadiens organization salutes and pays tribute to its former players. They invented passing the torch - in my opinion, nobody does it better. 

Respect.

Jean Beliveau and "Rocket" Richard

In 1997, Ken Dryden (of all people) was the president of the Leafs (no, it's not a misprint). The team wanted to pay tribute to the Top Maple Leafs of All Time. Dryden asked former HNIC executive Frank Selke Jr., who also served on the Hockey Hall of Fame selection committee, if he would help with the selections. Frank told me he was puzzled: "Where do I start"? As an example, Selke said, "Frank Mahovlich was thought to be a great Leaf (but had to deal with the likes of Punch Imlach, who made his life Hell). 

However, he had his best season ever when he lined up with Gordie Howe in Detroit and scored 49 goals, then went on to have another entire career as a Montreal Canadien and hoisted the Cup twice. Do fans think of Mahovlich as a Leaf, a Red Wing or a Hab? Incidentally, Mahovlich told me that one of his most memorable moments in the game was when he was told that "his image would be on the commemorative edition of the Canadiens' 100th anniversary gameday tickets." 

Selke had no trouble selecting the following former Leafs who went on to be selected to the Hockey Hall of Fame wearing a Leaf jersey: Kelly, Salming, Sittler, Keon Pulford, Stanley, Gilmour, Horton, Bower, Armstrong, Duff and Kennedy.

QUESTION: Are there only 11 Top Maple Leafs of All Time who are Honoured Members of the Hall from the last 75 years of the franchise?

Keep in mind, the following former Leaf players who are Hall members are mostly associated with the teams stated in brackets: Andreychuk (Buff/Tampa) Lindros (Philly) Anderson (Edmonton) Leetch (NYR) Francis (Pitt/Carolina) Murphy (Detroit) Fuhr (Edmonton) Gartner (Wash/NYC) Lanny (Calgary) Flaman/Boivan (Boston) Olmstead (Habs) Parent (Philly) Cheevers (Boston) Ullman (Detroit) Pronovost (Detroit) Bathgate (NYC) Dickie Moore (Habs) Plante (Habs) Sawchuck (Detroit) Pierre Pilote (Chicago) 

I cringe at the end of the hockey season, and my team makes an early exit and is on the golf course. For more than 50 years, I've heard and read Toronto hockey media types advise their audience, "If you want the team to improve, stay away from Leaf games until management improves the team. That instruction has always fallen on deaf ears.

It's time to face facts ... the Toronto Maple Leaf Hockey Club has simply become a synonym for "Corporate Hockey." The board of directors of Maple Leaf Sports and Entertainment Corporation appear to present itself that way. Look no further than the regular season games that have very quietly moved to pay TV for some games, and there are more to come. Effective this season, Rogers announced July24/26 that there will be across-the-board price increases and hold on to your hat if you live outside Leaf territory.

Clearly, Saturday night Leafs on Hockey Night in Canada is not a birthright. To MLSE, nothing, including winning hockey games, is more important than money.

Here's more proof, if you need it. 

I always thought it was a great idea for the team to dress up one of the kids and have them become a pregame flag bearer and skate the length of the ice in front of the sold-out Scotiabank Arena crowd. What a thrill for the kid. The truth is, it costs $956.83 for the 8 - 12-year-old skater, and he must purchase at least one ticket as well, but it's usually two tickets to include a parent or guardian.  That total sum, after 41 home games, could make a fine contribution to Toronto's Sick Children's Hospital if the club were more community-conscious -- like, say, the generous Tampa Bay Lightning hockey club, which donates $50,000 each week of the regular season to a local Tampa/St. Petersburg charity.

Another SIDEBAR QUESTION: June 16/26, Rogers Communications exercised its option on ownership of Hockey Night in Canada and gave the CBC the boot, after 74 years. If you liked the analysis of former NHLer Kelly Hrudey, he was removed from the broadcast in early June -- expect other HNIC favourites to depart as well. Do these moves by Rogers and MLSE bring us closer to what's mentioned in the paragraph above -- a shift toward more pay TV?

And, if you happen to be a baseball fan, you've already seen the move to PAY TV by the tall foreheads at Rogers -- more moves to PAY would have happened if this year's edition of the team was World Series-bound. Rogers owns the Blue Jays, the Blue Jay TV station, the Blue Jay radio station, and the stadium I still call Skydome. I was on the stadium's naming committee that selected "Skydome" before Rogers' money showed up.

QUESTION: Wasn't the CRTC (Canadian Radio Television Corp) created to make sure this type of media monopoly didn't happen?

Do we, as Canadians and hockey fans, not have a strong history and connection to the CBC version of HNIC? 

All of it - Ed Fitkin, Ward Cornell, Bill Hewitt, the Hot Stove Lounge, Foster announcing Keon as the game's first star (every game), Dave Hodge, Frank Selke Jr. on-ice interviews with Stanley Cup winners, Don & Ron -- it seemed familiar to us? Did Canadian (Leaf) hockey fans lose some currency in this sleight of hand by Rogers?

The Leafs are rebuilding (again). Are they at the back of the pack? Do you wonder what Vegas odds makers think about the blue and white's chances?

QUESTION ... this may be the biggest question of all: 

How long do you think it will take the Leafs franchise to reach the level of play of the Sabres or the Canadiens… not to mention Colorado, Vegas, Carolina, the new/improved Caps, or even Philly -- I don't know anything about their lineup. Still, Tocchet seems to be able to find a way to make lemonade out of lemons as GM; Briere has quietly been going about spending money in the right places.

August 1/2026, Chayka announced the hire of former Penguin staffer Andy O'Brien as the team's strength and conditioning coach. Every player in today's game has a very strict regime of diet and exercise; otherwise they don't last ... many don't understand this and don't make it past training camp. 

So the Penguins got our senior executive for contract and cap management + a proven goal scorer, and we got their strength and conditioning coach?

Gawd, I hope Dubas doesn't succeed.

Notice I didn't mention the Oilers ... betting pools are already in place to see how long Babcock will last.

QUESTION: (It may take a while for the Leafs to show progress) ... How long has it taken the Blackhawks to start to look like they may have "turned a corner" with their rebuild -- Bedard arrived 3 years ago -- and now they've got fan favourite, Patrick Kane back with the club for two years. I had my fingers crossed that Kane would become a Leaf and line up beside Matthews this year. He's a Hall of Fame lock, and might be Bedard's missing piece that helps move him into the goal-scoring stratosphere. The Blackhawks certainly look like they will be fun to watch.

ODDBALL QUESTION: Do you think Chicago has the best-looking logo in the NHL?

But, back to the Leafs ... Grit, or lack of it, has been a recurring description of the Leafs for quite a while. 

QUESTION: Did the search for grit start when, in Nov. 2008, new GM Brian Burke announced, "we require, as a team, proper levels of pugnacity, testosterone, truckulence and belligerence ... that's how our team plays"? And then the team chose to take the opposite route?

(Personally, I loved it when Burke made the statement above and emphasized the word truckulence ... he sounded like another blow-hard, "Pal Hal")

Not to be outdone, the new Leaf coach, Jim Hiller, was quoted as saying, "Toronto's style of play under my guidance will be aggressive, unrelenting mobility". You can't make this stuff up!

Well, we will see, coach.

Have you noticed the intensity, grit, ugliness, and determination each player had for the 2026 Vegas - Colorado series? Everybody showed up angry. Every game was a war. Vegas had 122 hits vs 97 hits for Colorado. Do you think last year's edition of the Leafs could have played at their level?

This ain't LA, Jim.

Coach Hiller seems quick on his feet, thoughtful, eloquent and very excited to be in LeafLand. He'll need all of those characteristics in spades because he'll have his hands full working in the heat of Toronto's media.

The Hockey News.com claims he finished 24th in the NHL head coach rankings. 

As of August 1/2026, Vegas oddsmakers have the Leafs in the middle of the Stanley Cup hunt for 2026/27 ... with Utah ahead of them! Utah?

Over to You ... Any Questions?

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