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

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

It was the morning of the Maple Leafs vs. Panthers Game 6. As he stood behind the glass for one of his last moments as president of the Leafs, Brendan Shanahan observed one of the pillars of his time up close.

Along with Auston Matthews, Mitch Marner, and William Nylander, Tavares was the final piece of the puzzle that completed Shanahan’s Leafs’ core and was meant to turn the team into Stanley Cup champions. The president was finally overthrown in Toronto because of his unwavering faith in that core.

On Thursday, Shanahan and the Leafs announced their separation after 11 years.

In an X statement, Shanahan stated, “Although I am proud of the rebuild we started in 2014, ultimately, I came here to help win the Stanley Cup, and we did not.”. “My biggest regret is that we were unable to complete the job, and there is nothing else I wanted to give our fans.”. “.”.

We need to look more closely at all 11 years, the highs and lows, and everything in between, to understand how a tenure that started with so much promise turned into something so stale and sour.

Part 1: Transformation of culture.

According to Tim Leiweke, the Leafs had a “culture problem.”. “.”.

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

Shanahan was that someone.

The year was spring 2014. Shanahan had no prior experience working in an NHL front office. For the previous five years, he had been employed by the league’s headquarters. As a player, he had demonstrated the traits Leiweke hoped the Leafs would have. In his 21 seasons, Shanahan had won three Stanley Cups and advanced to the playoffs 19 times.

“I appreciate his fervor.”. His work ethic is admirable. On April 14, 2014, the day Shanahan was formally introduced as team president, Leiweke remarked, “I appreciate his analytical skills.”. He doesn’t make snap decisions, which I like. “”.

There would be no “big speeches, big words, big proclamations,” according to Shanahan. “”.

He declared, “What we say here today is irrelevant.”. It’s about the effort we make. It’s all about the outcomes. “.”.

Since 2004, the Leafs had only once qualified for the playoffs in a ten-year span. There weren’t many results. With 12 defeats in the last 14 games, a team captained by Phil Kessel and Dion Phaneuf fell out of postseason contention that spring.

Nevertheless, Randy Carlyle, the current coach, was given a two-year extension.

Shanahan told James Mirtle of the Globe and Mail at the time, “A lot of people said ‘Oh OK, so that’s it, we’re coming back with the exact same group,'” when they heard the news about Randy. “Well, we aren’t. However, there will be no time constraint on the pressure to make decisions. “.”.

“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,” Shanahan said, generalizing his beliefs, which still hold true today. I have witnessed it with people. This guy is not your No, so you can’t win. Until they do and are seen as these outstanding leaders, you have one goalie or this guy as your captain.

In the playoffs, you really have to do that. Furthermore, a team’s reputation is built in the playoffs, so no amount of regular season success will help. It must be earned and you must get there. “”.

With the eighth pick that summer, the Leafs went all out and selected the extremely talented William Nylander. Shanahan stated, “I think he’s an exciting swing at a guy who could be a high, high top-end talent.”.

Shanahan made a shocking announcement later that summer when he hired 28-year-old Kyle Dubas from the Sault Ste., replacing assistant general manager Dave Poulin and Claude Loiselle. their place with Marie Greyhounds.

Being surrounded by “people that challenge ideas, that think differently” was something Shanahan desired. “.”.

Soon after, Mark Hunter—the longtime London Knights face—joined the front office to lead the development and draft departments.

In Carlyle, choosing to keep things as they were backfired; as the issues from the previous season only got worse, he was fired in early January 2015. Carlyle’s replacement didn’t help either, as the Leafs dropped 17 of their first 19 games under interim coach Peter Horachek.

In Toronto, it began to grow dark.

Following the 68-point season, general manager Dave Nonis was let go. So were several other staff members and the rest of the coaching staff.

Shanahan stated that co-GMs Dubas and Hunter, who had neither held a front office position in the NHL prior to joining the Leafs, would take charge of the organization in the interim.

Shanahan stated, “The vision remains unchanged.”. However, the plan is subject to change on a daily and weekly basis. because things change because it’s a sport. “.”.

Deals involving franchise mainstays Phaneuf and Kessel would not be ruled out by the Leafs. However, the group would exercise patience. The Leafs president possessed the “stomach” that was necessary for that in Toronto, “a place with this much passion.”. “.”.

“This organization has previously run into issues due to shortcuts,” he stated.

Shanahan was unable to predict how long it would take the Leafs to return to respectability. He questioned whether the individuals who came up with those solutions do so “just to buy themselves some time.”. “”.

However, the reality and the most accurate response I can provide is that it takes as long as it takes. “”.

Shanahan would take his time in finding someone, and he had no plans to become the general manager himself. Since Mike Babcock, the longtime coach of the Detroit Red Wings and Team Canada, was given a huge eight-year, $50 million contract, he would not rule out hiring a coach ahead of the general manager.

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

Dubas and Hunter would compete for dominance at the draft table because Shanahan had not yet appointed a full-time general manager.

When the Leafs selected Mitch Marner, a London-based player for Hunter, with the fourth pick, the process worked.

Dubas’ attempt to add more picks by trading down from the 24th pick—a pick that ended up being Travis Konecny—did not go as planned.

On Canada Day, the Leafs traded Kessel to Pittsburgh for a first-round pick and an unimpressive return that was emphasized by prospect Kasperi Kapanen, underscoring Shanahan’s front office’s inexperience once again.

After a few weeks, when the offseason’s heavy lifting was completed, Shanahan finally chose his general manager. Lou Lamoriello, who will soon turn 73, was the most seasoned individual in the area, having drafted Shanahan into the NHL in 1987 and helping the New Jersey Devils win three Stanley Cups.

On his first official day, Lamoriello remarked, “I don’t know how many of you know Brendan as well as I do.”. “I can guarantee you that I will send Brendan if I want anyone to be recruited, wherever they may go. “.”.

Shanahan in particular and the Leafs would later regret Lamoriello’s first move as general manager. The New York Islanders received a package of prospects from the Leafs in exchange for Michael Grabner’s services for a year. One of those prospects is Carter Verhaeghe, a future 40-goal scorer for the Florida Panthers.

Later in the 2015–16 campaign, Lamoriello dealt Phaneuf to Ottawa, which resulted in a victory.

Some believed that Dubas would be mentored by the godfather of NHL general managers, but anyone who knew Lamoriello well knew that he was renowned for his secrecy. Like almost every other member of the front office, Dubas was largely excluded from important choices and allowed to manage the Toronto Marlies however he saw fit.

The majority of Dubas’s time was spent with Brandon Pridham, another early hire in Shanahan’s front office who has been crucial in helping to navigate the salary cap.

Section 2: Slippery progress.

Before the 2015–2016 season began, the Leafs had a strategy. Babcock was referring to the “pain.”. The first pick in the draft was theirs for the first time in thirty-one years after they bottomed out and won the draft lottery.

Following the Leafs’ victory in the lottery, Shanahan remarked, “I’ll just say that our scouts were very pleased with tonight’s results.”.

The victory changed the course of the franchise. The Leafs acquired their own future number one year after narrowly missing out on Connor McDavid in the lottery. 1 Auston Matthews center.

It was a faster rebuild.

The Leafs traded for a No. a few days before they selected Matthews. tried to entice hometown boy Steven Stamkos in free agency shortly after acquiring goalie number one in Frederik Andersen. His decision was to rejoin the Tampa Bay Lightning. ).

With Lamoriello and Babcock in charge, the culture shift Leiweke had promised came to pass. High jersey numbers, in-game promotions showcasing players, and facial hair were all prohibited by Lamoriello’s notorious regulations.

Shanahan, on the other hand, aimed to elevate one of the NHL’s Original Six teams back to prominence.

100 of the Leafs’ greatest players in team history were honored. In front of what was formerly the Air Canada Centre, a Legends Row was put up. A worn-out logo was swapped out for one that evoked tradition, and the team retired 16 numbers, including Dave Keon’s.

The Leafs saw a sharp improvement in the 2016–17 season under Matthews, Marner, and Nylander, as well as incumbents Morgan Rielly, Nazem Kadri, Tyler Bozak, and James van Riemsdyk and one of the NHL’s best coaches. In a tight six-game first-round series, they defeated the Presidents’ Trophy-winning Washington Capitals to secure a postseason berth.

However, Shanahan had either failed to notice or disregarded Lamoriello’s lack of expertise in the salary-cap era when he hired him.

In May, Nikita Zaitsev signed a seven-year contract extension worth $31.5 million with the Leafs general manager. Later that summer, he inked the soon-to-be 38-year-old Patrick Marleau to a costly three-year contract.

Eventually, the Leafs would have to give up both players and their onerous contracts in order to acquire valuable assets.

Out of sight, a largely unnoticed subplot took place that spring when Shanahan gave Dubas permission to interview for the GM position in Colorado and, if offered, accept it.

The Avalanche wanted Dubas to lead the team with Joe Sakic’s assistance after a terrible 48-point season.

A year later, Shanahan fired Lamoriello as general manager and brought in Dubas.

“Everything I’ve ever tried to do was what I thought was the best decision for the Toronto Maple Leafs,” Shanahan said, referring to the franchise’s decision to entrust it to the inexperienced Dubas as “unconventional.”. Certain tasks necessitate persistence, while others call for initiative.

“No one put any pressure on me to do this. “.”.

That summer, a rookie general manager had crucial, franchise-changing work to do.

Longtime Islanders captain and free agent John Tavares was successfully persuaded to sign a seven-year contract with the team by Dubas, Shanahan, and Babcock while they were in Los Angeles.

Tavares was the key that turned the Leafs from a brash upstart into a Stanley Cup contender. He was a two-time Hart Trophy finalist. The expectations immediately rose.

But complaints also spread to the organization’s periphery. The concern was that, with Tavares earning $11 million a season, the Leafs would not be able to retain all of their young players. For the team’s other stars, Matthews and Marner, his contract set a high standard.

A quicker response from the front office might have avoided that issue.

“Take time when time is available” was Lamoriello’s motto. Dubas had to make a deal because he had failed to extend Nylander’s contract the previous summer, and extensions for Matthews and Marner were also imminent.

For a president and general manager who were inexperienced in such matters, it was high-stakes work.

Just like when he played in Detroit, Shanahan thought his players would accept less money in the name of team success.

“Not everyone is a good fit for it,” Shanahan stated. However, that’s what they want or what we want from the people who will be playing here, and I believe that’s what they want from one another. “.”.

The Leafs’ young stars had a different perspective.

Nylander waited until December. Before ultimately agreeing to a six-year contract worth an average of $7.51 million per year, he played one game of that 2018–19 season. The contract dispute lasted the longest during the salary-cap era for the Leafs.

A deal with Matthews was reached by the Leafs two months later, but it went against Shanahan’s wishes. The contract had a $11 million cap hit at the start, which was third-highest in the league, and it was only for five seasons.

The Leafs suffered a seven-game loss to the Bruins in a first-round series for the second time in as many seasons, and Kadri was suspended during that time.

At first, Dubas would not confirm if Babcock, the coach he did not hire, would be coming back. On May 6, he finally said to Bob McKenzie of TSN, “Mike is all in on us, and we’re all in on Mike.”. “.”.

The Leafs then declared that Shanahan had been given a six-year contract extension, which would keep him with the team until the 2024–25 campaign.

After just one season, the Leafs sent Kadri to Colorado, who had been suspended in both of the previous postseasons, in what swiftly turned into a regrettable trade for the Leafs, ending the potentially disastrous 1-2-3 center combination of Matthews, Tavares, and Kadri.

That autumn, Tavares was installed as captain.

Part 3: Unmoving and stuck.

Like Nylander and Matthews, Marner refused to accept a lower salary on his second NHL contract. And a day into training camp, the Leafs gave in to his demands with a six-year contract and one of the biggest cap hits in the league — $10.9 million — rather than face another protracted contract dispute that could ruin another season.

The Leafs could have gotten more value if they had taken action sooner with all three players. Marner, for example, may have consented to an eight-year contract last summer that included an $8 million cap hit.

When the Leafs struggled early in the 2019–20 season, the coach-before-GM hire finally backfired. In order to fire Babcock directly, Shanahan traveled to Arizona in November.

In reference to the choice to replace Babcock with Sheldon Keefe, a Dubas protégé who had never served as an NHL coach, Shanahan stated, “We’re making moves and we’re evolving as we see we have to do.”. “You don’t start with an idea or a plan and then not change or adapt it as you go along. “”.

Keefe’s strategies were in opposition to Babcock’s. He was more inventive and creative.

Marner was abruptly permitted to play alongside Matthews on the same line. Nylander and Tavares also joined them in the power play. Under Shanahan’s direction, the Leafs, one of the first teams to use analytics, valued puck possession.

Keefe’s promising start turned sour before the pandemic ended the regular season. Columbus then defeated them in a lackluster play-in round match.

The Leafs appeared ready to advance to their first Stanley Cup final since 1967 after dominating the so-called Canada Division the following regular season. However, in yet another early playoff loss, a 3-1 lead to Montreal in the first round of the series vanished.

When it counted most, Shanahan’s stars did not deliver.

Following the defeat, Shanahan stated on a video call, “We are going to do this here in Toronto with this group.”. Among the teams he cited were the Washington Capitals, who had won the Cup in 2018.

Shanahan claimed that the teams that were smart enough to hold onto their stars, surround them, and help them grow were the ones who eventually prospered.

The roster would change, but not with Matthews, Tavares, Marner, and Nylander in the top four. “You simply cannot give up on these guys,” Shanahan remarked. “You simply cannot give up on players who are so invested—and they are.”. “”.

The salary-cap freeze brought about by the pandemic’s financial realities, however, made it even harder to hold onto players because the Leafs’ flexibility was restricted by a flat cap. Zach Hyman and Andersen were permitted to enter free agency by the team.

The Leafs responded with a franchise-high 115 points, which was second in the Atlantic Division but fourth in the NHL that season, demonstrating their resolve to make the regular season count. which resulted in a narrow seven-game series loss for the Leafs against the reigning champion Lightning in the first round.

“There will definitely be new faces as we look forward to next year,” Shanahan remarked afterwards. Having said that, we won’t be making changes merely to claim to have done so. “.”.

That is, the core would remain.

Part Four: The start of the end.

Dubas’ five-year contract ended the following season.

Discussions about an extension were supposed to happen in the summer of 2022, but that never happened. Shanahan told his GM there would be no extension at all by the fall. Ownership wanted to see some postseason results, was the message.

This implied that Dubas was a mediocre general manager whose success depended on the playoffs. If they wanted to, the Leafs would also need to negotiate a new contract for their general manager as soon as the season ended, at whatever time.

Shanahan and Dubas had spent years watching home games together in a plush box at Scotiabank Arena. Not any more. In the press room, Dubas sat in the general manager’s box for the first time during his tenure for the 2022–2023 season.

Shanahan observed from afar.

The Leafs had a rough start but ended up finishing second in the Atlantic and amassing 111 points, the second-highest total in the team’s history.

With the help of the team’s star players, Matthews, Nylander, and Tavares, as well as their big-name trade-deadline acquisition, Ryan O’Reilly, they finally defeated the Lightning in the first round.

It was followed by a terrible five-game loss to the Panthers in the second round. Organizational chaos also occurred.

It was preferred by the Leafs that Dubas hold off on discussing his thoughts on the season until after his contract was finalized. He would rather not leave Keefe and the other members of his team to bear the blame for the loss alone. Dubas expressed his emotional reluctance to stay on the position.

Additionally, he alluded to the core’s eventual modification.

In the middle of contract negotiations, Shanahan fired him a few days later. He expressed his admiration for Dubas’ performance that season, citing his acquisitions of O’Reilly and Luke Schenn at the deadline, but he expressed concern about Dubas’ hesitancy to stay as general manager.

Shanahan pushed out the GM in what appeared to be a power struggle after Dubas sent an email reiterating his intention to stay. In the end, ownership determined that Shanahan was more important.

Internally, there was indignation over the decision.

GM Dubas was far from flawless. If he had been extended after, say, the 115-point season, would the core have been different after the Panthers’ defeat, and would Marner, who has no no-trade protection until July 1, have been dealt? Would the franchise’s history have been different?

Brad Treliving became Shanahan’s third general manager appointment. (Getty Images via Toronto Star/Andrew Francis Wallace).

Rather, Shanahan quadrupled down on the core after Dubas left.

Brad Treliving, Dubas’ successor, felt the Leafs needed more “snot” to contend in the postseason, so he brought in Ryan Reaves, Tyler Bertuzzi, and Max Domi. After Keefe’s contract was extended by the redesigned front office, Matthews signed a four-year extension, making him the highest paid player in the league. In January, Nylander was given an eight-year extension.

Hall and Oates’ “You Make My Dreams,” a Shanahan favorite, was finally dropped by the Leafs as the team’s goal song after five seasons.

Treliving subsequently referred to the Leafs’ season as “uneven.”. Despite Matthews’ franchise-high 69 goals, the Leafs ended the season with 102 points, nine less than they had the year before. Due to injuries to Nylander and Matthews, they suffered another seven-game first-round series loss to the Bruins. In a Game 7 defeat, the Leafs only managed one goal.

Only one playoff round had been won by the Leafs ten years after Shanahan’s declaration that “we need to have results here.”.

The new MLSE president and CEO, Keith Pelley, chose to keep Shanahan on board.

Shanahan alluded to a shift once more.

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

It was only talk, it turned out. Once again, the Leafs maintained their core, choosing to switch up the strategy and voice behind the bench.

Craig Berube, a Stanley Cup-winning coach who would implement a direct, weighty, and risk-averse style that the team believed would increase postseason success, took Keefe’s place after he was fired.

Chris Tanev and Oliver Ekman-Larsson, two seasoned defenders, were added to strengthen the blue line. The crease was cemented by Treliving and Anthony Stolarz.

But in the end, the Leafs were once again relying on their enduring core to win them a championship.

Despite the lackluster season, the team managed to accumulate 108 points and win the Atlantic for the first time. A rumored (and much too late) trade of Marner for Mikko Rantanen also failed, as did attempts to extend Marner’s contract.

In a battle of the Ontario, the Leafs rallied to win the first round in six games.

However, a 2-0 series advantage over the reigning champion Panthers vanished. The Leafs suffered another defeat in a disappointing Game 7, this time a humiliating 6-1 thumping at home.

Game 7 was Shanahan’s Leafs’ sixth defeat in six tries.

The Leafs won two playoff rounds and, most importantly, no Stanley Cups in his 11 seasons. They were not able to make it past the second round.

Success, which Shanahan once said was the only thing that mattered, turned out to be elusive. The Shanaplan had not worked out.

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

(Photo by USA Today Sports/Tom Szczerbowski at the top).