Brendan Shanahan’s Maple Leafs odyssey: Vision, hope, stubborn belief and failure

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John Tavares caught passes on his backhand at the Baptist Health Iceplex in Fort Lauderdale.

It was the morning before Game 6 between the Maple Leafs and Panthers. Brendan Shanahan stood behind the glass watching one of the cornerstones from his era up close for one of the final times as president of the Leafs.

Tavares had been the last puzzle piece to join the core of Shanahan’s Leafs, the one who was supposed to transform the team, along with Auston Matthews, Mitch Marner and William Nylander, into Stanley Cup champions. It was the president’s unyielding belief in that core that ultimately led to his undoing in Toronto.

Shanahan and the Leafs parted ways after 11 years on Thursday.

“While I am proud of the rebuild we embarked on starting in 2014, ultimately, I came here to help win the Stanley Cup, and we did not,” Shanahan said in a statement on X. “There is nothing more I wanted to deliver to our fans, and my biggest regret is that we could not finish the job.”

How did a tenure that began with so much promise grow into something so stale and sour? To find out, we need to take a closer look back at all 11 years — the ups, the downs, and everything in between.

Part 1: Culture change

In Tim Leiweke’s estimation, the Leafs had a “culture problem.”

The president of Maple Leaf Sports and Entertainment believed the team lacked “identity” and “direction” and needed somebody who would become “the culture, the heart and soul, and the character of the organization.”

That somebody was Shanahan.

It was the spring of 2014. Shanahan had never worked in an NHL front office before. He had spent the previous five years working for the league’s head office. As a player, he’d embodied the qualities Leiweke wanted to see in the Leafs. Shanahan had been to the playoffs in 19 of his 21 seasons, winning three Stanley Cups.

“I like his passion. I like his work ethic. I like his analytical skills,” Leiweke said on April 14, 2014, the day Shanahan was officially introduced as team president. “I like (that) he doesn’t knee-jerk.”

Shanahan said he wouldn’t deliver any “big speeches, big words, big proclamations.”

“Nothing we say here today matters,” he said. “It’s about the work we put in. It’s about results.”

The Leafs had made the playoffs only once in the decade since 2004. Results were in short supply. A team led by Phil Kessel and Dion Phaneuf nosedived out of postseason contention that spring with 12 losses in the final 14 games.

Incumbent coach Randy Carlyle was nonetheless signed to a two-year extension.

“When we made the announcement about Randy, a lot of people said ‘Oh OK, so that’s it, we’re coming back with the exact same group,’” Shanahan told James Mirtle, then of the Globe and Mail. “Well, no, we’re not. But the pressure to make decisions won’t be dictated by a timeline.”

Speaking more generally about his beliefs, which resonate even more today, Shanahan said that, “Too many times in my life, teams described as not capable of winning the big game and then suddenly they win the big game and the perception changes. I’ve seen it with individuals. You can’t win with this guy as your No. 1 goalie or this guy as your captain until they do it and they’re perceived to be these great leaders.

“The reality is you have to do that in the playoffs. And no amount of success in the regular season is going to — reputations are made in the playoffs. You have to get there and you have to earn it.”

That summer, the Leafs swung for the fences at the draft, opting for the uber-skilled William Nylander with the eighth pick. “For me, he’s an exciting swing at a guy that could be a high, high top-end talent,” Shanahan said.

Later that summer, Shanahan made a surprise announcement when he fired assistant GMs Dave Poulin and Claude Loiselle, and hired 28-year-old Kyle Dubas from the Sault Ste. Marie Greyhounds in their place.

Shanahan wanted to be surrounded by “people that challenge ideas, that think differently.”

Mark Hunter, the longtime face of the London Knights, joined the front office soon after to spearhead the draft and development sectors.

Opting for the status quo in Carlyle backfired; he was fired in early January 2015 as the problems of the previous season only grew worse. They didn’t get any better with Carlyle’s replacement as the Leafs lost 17 of interim coach Peter Horachek’s first 19 games.

Dave Nonis, Kyle Dubas, Cliff Fletcher and Brendan Shanahan during the 2014-15 season. (Bernard Weil / Toronto Star via Getty Images)

It got dark in Toronto.

GM Dave Nonis was fired after the 68-point season. So was the rest of the coaching staff, as well as a number of other staffers.

Shanahan said the organization would be led in the interim by co-GMs Dubas and Hunter, neither of whom had worked in an NHL front office before joining the Leafs.

“The vision doesn’t change,” Shanahan said. “But the plan changes day to day, week to week. Because it is a sport and things change.”

The Leafs wouldn’t rule out trades involving franchise cornerstones Phaneuf and Kessel. But the team would remain patient. The president of the Leafs had the strong “stomach” required for that in Toronto, “a place with this much passion.”

“Shortcuts have gotten this organization into trouble in the past,” he said.

How long would it take for the Leafs to reach respectability again? Shanahan couldn’t say. He wondered if the people who came up with those answers do so “just to simply buy themselves some time.”

“But the truth of the matter is, and the reality, and the truest answer I can give you: it takes as long as it takes.”

Shanahan had no intention of becoming the GM himself, nor would he rush the process of finding someone. He wouldn’t rule out hiring a coach before the GM, which is exactly what he did when Mike Babcock, the longtime coach of the Detroit Red Wings and Team Canada, was signed to a monster eight-year, $50 million contract.

“If you think there’s no pain coming,” Babcock memorably said on the day in May 2015 when he was introduced as Leafs coach, “there’s pain coming.”

Shanahan still hadn’t hired a full-time GM when the draft got underway, which meant Dubas and Hunter would wrestle for control at the draft table.

With the fourth pick, the process worked when the Leafs selected Mitch Marner, who played for Hunter in London.

Dubas’ bid to add more picks, trading down from the 24th selection, a selection that became Travis Konecny? Not so much.

The inexperience of Shanahan’s front office was highlighted once again on Canada Day when the Leafs traded Kessel to Pittsburgh for an underwhelming return highlighted by prospect Kasperi Kapanen and a first-round pick.

A few weeks later, after the heavy lifting of the offseason was already done, Shanahan finally picked his GM: soon-to-be-73-year-old Lou Lamoriello, the most experienced person around, someone who had drafted Shanahan into the NHL in 1987 and the architect of three Stanley Cups with the New Jersey Devils.

“I don’t know how many of you know Brendan as well as I do,” Lamoriello said on his first official day. “I can tell you that if I want anybody recruited, anywhere to go anywhere, I’m sending Brendan.”

Mike Babcock signed a monster $50 million contract in May 2015. (Dan Hamilton / USA TODAY Sports)

Lamoriello’s first move as GM was one the Leafs, and Shanahan especially, would come to regret. For one year of Michael Grabner’s services, the Leafs sent a package of prospects to the New York Islanders. Among those prospects: future Florida Panthers 40-goal scorer Carter Verhaeghe.

Later in that 2015-16 season, Lamoriello scored a win when he dealt Phaneuf to Ottawa.

There was some thought that the godfather of NHL GMs would mentor Dubas, but anyone who truly knew Lamoriello knew he was famously secretive. Like just about everyone else in the front office, Dubas was mostly siloed from major decisions, left to run the Toronto Marlies as he saw fit.

Dubas spent most of his time with Brandon Pridham, another of the early hires in Shanahan’s front office, and someone who’s played an invaluable role navigating the salary cap.

Part 2: Bumpy progress

The Leafs had a plan going into the 2015-2016 season. It was the “pain” that Babcock talked about. They bottomed out and won the draft lottery, earning the first pick in the draft for the first time in 31 years.

“I’ll just say that our scouts were very pleased with tonight’s results,” Shanahan said after the lottery balls fell in the Leafs’ favour.

It was a franchise-altering win. One year after coming up just short in the lottery for Connor McDavid, the Leafs netted their own future No. 1 centre in Auston Matthews.

The rebuild sped up.

Days before they selected Matthews, the Leafs traded for a No. 1 goaltender in Frederik Andersen and tried to lure hometown boy Steven Stamkos in free agency soon after. (He opted to return to the Tampa Bay Lightning.)

The culture change that Leiweke promised took effect with Lamoriello and Babcock running the show. Lamoriello’s infamous rules meant facial hair, high jersey numbers and in-game promotions featuring players were all off-limits.

Shanahan, meanwhile, sought to restore prestige to one of the NHL’s Original Six franchises.

The Leafs honoured the 100 greatest players in team history. A Legends Row was installed in front of what was then known as the Air Canada Centre. The team retired 16 numbers, including Dave Keon’s, and replaced a tired logo with one that spoke to tradition.

With Matthews, Marner and Nylander, as well one of the NHL’s top coaches and incumbents Morgan Rielly, Nazem Kadri, Tyler Bozak and James van Riemsdyk, the Leafs improved rapidly in the 2016-17 season. They won a playoff spot and pushed the Presidents’ Trophy-winning Washington Capitals hard in a close six-game first-round series.

A true superstar in Auston Matthews and a championship-calibre coach in Mike Babcock gave fans hope in the Shanaplan. (Kevin Sousa / NHLI via Getty Images)

Lamoriello was no master of the salary-cap era, though — something Shanahan had either overlooked or ignored in hiring him.

In May, the Leafs GM signed Nikita Zaitsev to a seven-year contract extension worth $31.5 million. He added Patrick Marleau, soon to be 38, to a pricey three-year deal later that summer.

The Leafs would eventually have to attach meaningful assets to trade away both players and their burdensome contracts.

A mostly overlooked subplot occurred out of sight that spring when Shanahan allowed Dubas to interview for the GM’s job in Colorado — and presumably take it, if offered.

Coming off a dreadful 48-point season, the Avalanche wanted Dubas to run the team with help from Joe Sakic.

Ultimately, Dubas was prevented from taking the promotion. It was the first crack in a relationship between Shanahan and Dubas that would eventually break entirely.

Shanahan pushed Lamoriello out as GM and replaced him with Dubas a year later.

Entrusting the franchise to the still-inexperienced Dubas may have been “unconventional,” Shanahan said, but “everything I’ve always ever tried to do was what I thought was the best decision for the Toronto Maple Leafs. Some of those things require patience and some of them require being proactive.

“I was under no pressure from anyone to do this.”

There was important, franchise-altering work to be done that summer — by a rookie GM.

Dubas, Shanahan and Babcock travelled to Los Angeles to successfully woo long-time Islanders captain and free agent John Tavares into coming home on a seven-year contract.

A two-time finalist for the Hart Trophy, Tavares would be the piece that transformed the Leafs from frisky upstart into Stanley Cup contender. Expectations increased instantly.

But grumbling on the outskirts of the organization also took hold. The Leafs, as the worry went, wouldn’t be able to keep all their young stars with Tavares making $11 million a season. His contract also established a high benchmark for the team’s other stars, namely Matthews and Marner.

That might not have been a problem had the front office acted sooner.

Lamoriello lived by the mantra of taking time when time was available. He failed to extend Nylander’s contract the previous summer — which meant Dubas was now on the clock to get a deal done, with extensions for Matthews and Marner also looming.

It was high-stakes work for a president and GM who had no experience in such matters.

Signing John Tavares was supposed to take the Leafs to the next level. (Carlos Osorio / Toronto Star via Getty Images)

Shanahan believed his players would take less money in the name of team success, just as they did in Detroit when he played.

“It’s not for everyone,” Shanahan said. “But for the ones that will play here, that is what they want or that’s what we want from them and I think that’s what they want from each other.”

The young stars of the Leafs thought differently.

Nylander sat out until Dec. 1 of that 2018-19 season before he finally agreed to a six-year contract with an annual average value of $7.51 million. It was the longest Leafs contract dispute in the salary-cap era.

Two months later, the Leafs got a deal done with Matthews — but one that ran counter to Shanahan’s desires. The deal was for only five seasons and came with an $11.6 million cap hit that ranked third-highest in the league when it began.

For the second time in as many seasons, the Leafs lost a first-round series to the Bruins in seven games and lost Kadri to a suspension along the way.

Initially, Dubas declined to say whether Babcock, the coach he didn’t hire, would return. Finally, on May 6, he told TSN’s Bob McKenzie, “We’re all in on Mike and Mike is all in on us.”

Soon after, the Leafs announced that Shanahan had received a six-year extension that would keep him with the team through the 2024-25 season.

The potentially devastating 1-2-3 centre combo of Matthews, Tavares and Kadri ended after only one season when the Leafs sent Kadri, suspended in each of the previous two postseasons, to Colorado in what quickly became a regrettable trade for the Leafs.

Tavares was named captain that fall.

Part 3: Stuck and not budging

Just like Nylander and Matthews, Marner declined to take less on his second NHL contract. And rather than endure another lengthy contract dispute that might derail another season, the Leafs capitulated to his demands one day into training camp with a six-year deal and one of the largest cap hits in the league — $10.9 million.

Had they acted sooner with all three players, the Leafs might have been able to score more value. Marner, for instance, might have agreed to an eight-year deal, with an $8 million cap hit, the previous summer.

The coach-before-GM hire ultimately backfired when the Leafs struggled at the outset of the 2019-20 season. Shanahan flew down to Arizona that November to fire Babcock himself.

“We’re making moves and we’re evolving as we see we have to do,” Shanahan said of the decision to replace Babcock with Sheldon Keefe, a Dubas protege who had never coached in the NHL. “You don’t set out with an idea or a plan and not evolve or make shifts throughout that plan.”

Dubas and Shanahan failed to find bargains when negotiating with Matthews, Nylander and Marner. (Nathan Denette / The Canadian Press via AP)

Keefe’s methods ran counter to Babcock’s. He was more creative and experimental.

Matthews and Marner were suddenly allowed to play on the same line together. They joined forces, with Nylander and Tavares, on the power play, too. The Leafs, among the early adopters of analytics under Shanahan’s watch, prized possession of the puck.

A promising start under Keefe soured before the regular season was shut down due to the pandemic. A lacklustre play-in round loss to Columbus followed.

The Leafs dominated the so-called Canada Division the following regular season and looked primed to march to their first Stanley Cup final since 1967. A 3-1 first-round series lead to Montreal evaporated, though, in yet another early playoff exit.

The stars that Shanahan so believed in failed to come through when it mattered most.

“We are going to do this here in Toronto with this group,” Shanahan said on a video call after the loss. He referenced teams like the Washington Capitals, who had won the Cup in 2018, in his reasoning.

“The teams that were wise enough to hang onto (their stars), and to continue to surround them and develop them, and just keep trying and trying and getting better and improving, benefited eventually,” Shanahan said.

There would be tweaks to the roster, but not with the top four of Matthews, Tavares, Marner and Nylander. “You just can’t quit on these guys,” Shanahan said. “You just can’t quit on players that care so much — and they do.”

But the financial realities of the pandemic created a salary-cap freeze that made holding onto players all the more difficult as a flat cap limited the Leafs’ maneuverability. The team allowed Andersen and Zach Hyman to walk in free agency.

Determined to make the regular season matter, the Leafs responded with a franchise-record 115 points, fourth-most in the NHL that season but second-most in the Atlantic Division. Which meant a first-round matchup with the defending champion Lightning, which the Leafs lost in a close seven-game series.

“Certainly, as we look forward to next year, there’s always going to be new faces,” Shanahan said afterward. “That being said, we will not be making changes just simply for the sake of saying that we made changes.”

In short, the core would stick around.

Part 4: The beginning of the end

The following season was the last on Dubas’ five-year contract.

There was an expectation that extension talks would take place in the summer of 2022, but that didn’t happen. By the fall, Shanahan had informed his GM there would be no extension at all. The message: Ownership wanted to see some results in the postseason.

Which meant that Dubas was a lame-duck GM, whose fate was tied to the playoffs. And the Leafs would have to negotiate a new deal for their GM, if so desired, immediately after the season, whenever that was.

For years, Dubas and Shanahan had watched home games together in a luxury box at Scotiabank Arena. No more. For the 2022-23 season, Dubas took a seat in the GM’s box in the press area for the first time in his tenure.

Shanahan watched from elsewhere.

The Leafs started poorly, but eventually piled up 111 points (second-most in franchise history) and another second-place finish in the Atlantic.

Victory finally came in a first-round win over the Lightning as the stars — Matthews, Nylander and Tavares, as well as marquee trade-deadline acquisition Ryan O’Reilly — pushed the team over the top.

A disastrous five-game second-round loss to the Panthers followed. So did organizational chaos.

The Leafs preferred that Dubas wait to share his thoughts on the season until after his contract had been taken care of. He preferred not to leave the rest of his team (the players and Keefe) out there alone to answer for the defeat. Dubas spoke emotionally about his reservations with continuing in the job.

He also hinted at finally changing the core.

Days later, Shanahan fired him in the midst of contract negotiations. He praised the job Dubas had done that season, including the deadline acquisitions of O’Reilly and Luke Schenn, but said he was bothered by Dubas’ uncertainty about remaining as GM.

An email from Dubas reaffirming his desire to stay didn’t sway Shanahan, who pushed out the GM in an apparent struggle for power. Ownership, in the end, had decided Shanahan was more essential.

The decision was met with outrage internally.

Dubas was far from a perfect GM. But would the course of history for the franchise have changed if he’d been extended following, say, the 115-point season? Would the core have been changed following the loss to the Panthers? Would Marner, with zero no-trade protection until July 1, have been dealt?

Brad Treliving became the third GM hire of Shanahan’s tenure. (Andrew Francis Wallace / Toronto Star via Getty Images)

Instead, with Dubas gone, Shanahan quadrupled down on the core.

Dubas’ replacement, Brad Treliving, felt the Leafs needed more “snot” to compete in the postseason and signed Ryan Reaves, Max Domi and Tyler Bertuzzi to bring it. The revamped front office, which extended Keefe’s contract, got Matthews signed to a four-year extension that made him the highest-paid player in the league. An eight-year extension for Nylander followed in January.

After five seasons, the Leafs finally dumped Shanahan favourite “You Make My Dreams” by Hall & Oates as the team’s goal song.

The Leafs had what Treliving would later describe as an “uneven” season. Even with Matthews scoring a franchise-record 69 goals, the Leafs finished with 102 points, nine fewer than the year previous. They lost one more seven-game first-round series to the Bruins amid injuries to Matthews and Nylander. The Leafs scored only once in a Game 7 loss.

A decade after Shanahan’s “we need to have results here” proclamation, the Leafs had won just a single playoff round.

Keith Pelley, the incoming president and CEO of MLSE, decided to hang onto Shanahan anyway.

Shanahan again hinted at change.

“When you see patterns not change … where you change things around some of your core issues hoping that this year the results will be different and they don’t (change), that’s when you start having to reassess from a different lens,” he said.

It proved to be just talk. The Leafs kept their core intact once again, opting instead to swap the voice and strategy behind the bench.

Craig Berube joined the Leafs after another Game 7 loss to the Bruins. (Dan Hamilton / USA Today Sports)

Keefe was fired and replaced with Craig Berube, a Stanley Cup-winning coach who would install a direct, heavy and risk-averse style that the team theorized would lead to greater postseason success.

Veteran defenders Chris Tanev and Oliver Ekman-Larsson were brought in to beef up the blue line. Treliving solidified the crease with Anthony Stolarz.

In the end, though, the Leafs were once again betting on their long-time core to deliver them a championship.

It wasn’t the prettiest of seasons, but the team still racked up 108 points and won the Atlantic for the first time. Attempts to extend Marner’s contract failed, as did a purported (and far too late) Marner-for-Mikko Rantanen swap.

The Leafs worked their way through the first round in six games in a Battle of Ontario revival.

A 2-0 series lead over the defending champion Panthers disappeared, though. Once again, the Leafs fell in a disappointing Game 7 — this time an embarrassing 6-1 blasting at home.

It was the sixth loss in six tries for Shanahan’s Leafs in Game 7.

In his 11 seasons, the Leafs won only two playoff rounds and, crucially, zero Stanley Cups. They failed to advance beyond the second round.

The success that Shanahan once described as all that really mattered proved elusive. The so-called Shanaplan had failed.

“You have to get there,” he said, “and you have to earn it.”

(Top photo: Tom Szczerbowski / USA Today Sports)

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