Maple Leafs Sports & Entertainment announced on Tuesday a new contract extension for Toronto Maple Leafs President and Alternate Governor Brendan Shanahan that runs through the 2024-25 season.

“On behalf of the MLSE Board of Directors, and certainly our company and fans as well, we are very pleased to see Brendan continue in his role as President of the Toronto Maple Leafs,” said Larry Tanenbaum, Chairman of the Board for MLSE. “Brendan’s positive impact on this team has not only been felt on the ice, where the team is on an impressive path, but throughout the league, with the Leafs alumni, and in the community. We look forward to continued success for the Maple Leafs under Brendan’s leadership over the next six years.”

“One of the things we are most proud of at MLSE is our team leaders’ impact on each of our team’s successes and our company’s culture, and Brendan is a perfect example of that,” said Michael Friisdahl, President and CEO of MLSE. “He brings a championship attitude to the team and the entire organization.”

“When MLSE approached me several months ago to discuss an extension, I told them this would be quite simple as I’ve had no desire to leave what we’ve started here with the Maple Leafs,” said Shanahan. “I’m thankful to the Board of Directors, our coaches, trainers, management and office staff, and especially our players for the professionalism and dedication they display every day.”

It would be difficult to argue this is anything but a deserved show of faith from MLSE ownership in a President who, over his first contract (five years in length), has presided over the transformation of the Leafs organization from a laughing stock into a respected, perennially competitive team that is set up for sustainable success in the long run.

Shanahan’s reversed the losing culture while in the process making amends with some of the historical skeletons in the franchise’s closet by doing right by one of its most important all-time greats (Dave Keon) and pulling the trigger on the long-overdue move of retiring (rather than honouring) jersey numbers.

In general, under Shanahan’s stewardship, this is an organization that has started to make far better use of the unmatched financial resources at its disposal in order to become an actual first-rate, high-class organization that is truly deserving of the unrivaled fan support its always enjoyed through thick and thin. Shanahan doesn’t speak publicly all that often, preferring to leave the spokesperson duties for Dubas and Babcock, but when he does interview, he has always smartly articulated a coherent vision and shown unmistakable signs that his finger is firmly on the pulse of the fan base.

A few years ago (2016), MLHS’ Declan Kerin wrote up a list of the impressive accomplishments Shanahan piled up inside his first 24 months on the job.

Looking back, was it evil genius on the part of Brendan Shanahan? Did he see two and three steps ahead in paying a coach(es) to be the sacrificial lamb for a grander plan he was devising? If, on May 8th of 2014, you had a crystal ball and told a panicking Leafs fan that Shanahan was going to pull off the following over the course of the next two calendar years:

– Start his first draft by picking the most skilled player, foregoing a tantalizing 6’3, 225 power forward, with their eighth overall pick.

– Let Carlyle coach the team as it predictably tailspun out of control, fire him, and let a powerless assistant coach help steer the team into the draft lottery.

– Actually trade the iron-clad contract of David Clarkson for Nathan Horton.

– Participate in and/or preside over one of the largest bloodlettings in NHL history: firing Dave Nonis, Peter Horachek, assistant coach Steve Spott, video coach Chris Dennis, goalie coach Rick St. Croix, chief pro scout Steve Kasper, and director of player development Jim Hughes. And then approve Mark Hunter’s firing of a staggering 18-plus scouts on top if it.

– A month later, in a grand and much-hyped whale hunting expedition, hire what many consider to be the best coach in the world in Mike Babcock — a move that many considered to be a fanciful pipe dream of only the most delusional fans.

– Hire the runner-up OHL coach of the year to coach the Marlies.

– Watch a first-time 28-year-old Assistant GM and Director of Player Personnel orchestrate a draft that saw the team curiously trade down and stockpile picks using value charts to draft highly skilled players one after another — a foreign concept to fans and media who follow the team closely, and one that was derided immediately by some traditionalist media types but widely praised by experts as a home-run draft and one of the best for the Leafs in decades.

– At the opening of free agency, trade the team’s best player — who he deemed to be the lynchpin for their lack of effort — in a “get him out of town” trade that seemed — and still seems — to be a bit light on returns, but underscored an aggressive and focused plan of peeling back the team to its studs and leaving no stone unturned.

– Sign primarily analytics-positive bargain players in free agency and not heed to the pressure of signing higher-profile players to bad contracts.

– Hire the lifetime New Jersey Devil and living legend General Manager, Lou Lamoriello — a perfect counterbalance after the criticism faced for assembling a front office staff scant on NHL executive experience.

– Finally admit that team is not going to be good and encourages the fans to hang in there, telling them that “there will be pain” and that their patience is appreciated.

– After the previous year of the tale wagging the dog and the media giving and getting more scandals than they could even handle (starting even before training camp), a much-needed airtight vacuum of information transfer creates a ghost town for the regular scoops and scandals.

– Watch as the newly-assembled and seemingly-unstoppable AHL team rips the league to shreds.

– Watch as the 2015 drafted prospects lead junior leagues in scoring at their respective positions at various points throughout the 2015-16 season.

– Instil a hard-working culture of defensively-responsible, tactically-nuanced and analytics-friendly hockey.

– Make amends with who many consider the best Maple Leaf of all time — Dave Keon — and lay to rest a decades-long standing feud — a feat attempted and failed by many.

– Introduce new young players from the AHL for cameos and send them back down once the team is playing too well.

– Trade your team captain’s long-term contract for futures with no salary retained.

– Build up and ship out players at the trade deadline to acquire more picks as you prepare for a last-place finish. Get 12 draft picks for the upcoming draft.

– Conduct a hard-earned, last-place finish that is somehow praised and applauded. Get a standing ovation at home from the fans at season’s end despite finishing dead last in the NHL.

– Win the draft lottery in a year that a unicorn — a big, extremely skilled, franchise centerman — is the clear-cut first overall pick.

– Watch your top junior prospect (Mitch Marner) win the OHL’s most outstanding player award.

– Prepare for your highly-favoured AHL team to push for the Calder Cup.

Three years later, you can add ending the organization’s playoff drought,  three straight playoff appearances, setting a new franchise record for regular season points (2017-18), recording back-to-back 100+ point seasons for the first time in franchise history (2018-19), and a Calder Cup championship (2018) to this list. That’s to say nothing of the organization’s expansion of its philanthropic contributions in the community, continued support for You Can Play and Pride, and much more.

All of that said, the next few years are bound to be challenging to navigate for Shanahan as the organization now looks to take the next step of actually winning playoff rounds and knocking on the door of a Stanley Cup championship.

There are incessant rumours of a coach-GM rift to some degree, or at a minimum, some clear signs of tension and disagreement between the two — and if it is to believed, on one side of that divide would be the GM he hired in Kyle Dubas, one he stuck his neck out for by ending his engagement with living legend Lou Lamoriello after the latter’s three-year contract concluded. On the other would be a HHOF-bound, Triple Gold-club head coach that he moved heaven and earth to court as the new face of the team and rebuild back in 2015.

There is also a major contract still due up for Mitch Marner and a maze of cap challenges in the team’s immediate and long-term future, and if there was a misstep from Shanahan so far in his time as Leafs President, it was speaking out during the William Nylander negotiations and hinting that hometown discounts akin to the ones from his (pre-cap, high-budget) Red Wing teams are going to be necessary in order to keep the team’s core together. The Matthews and Nylander contracts — and early reports of the nature of the Marner negotiations — have said this much loud and clear: Discounts are not a plan. 

There is no doubt Shanahan earned this show of faith today, but as the Leafs President well knows from his playing days, Stanley Cups are how the greats are truly measured — players, managers and Presidents alike. The next step is going to be the hardest to take.