Revisiting Brendan Shanahan's worst and best decisions as Maple Leafs President during his 11-year reign feat. Drafting Auston Matthews

The Toronto Maple Leafs officially announced that the team would not renew Brendan Shanahan’s contract, ending his tenure as the club’s President.

The announcement ended speculation following yet another disappointing playoff exit for the Maple Leafs. As such, it’s worth looking back at Shanahan’s 11-year reign in Toronto, focusing on the best and worst decisions as the team moves forward with a new voice at the helm.

Revisiting Brendan Shanahan's worst and best decisions as Maple Leafs President during his 11-year reign

Worst decisions

The so-called Core Four has failed to live up to expectations - Source: Imagn

Let’s start with the worst decisions during Brendan Shanahan’s tenure as Maple Leafs President.

The Core Four

The first thing that comes to mind is going with the Core Four structure. The organization committed more than half of its salary cap space to four players at one point during Shanahan’s time as President.

That situation made it extremely challenging for the team to round out the roster in support of stars Auston Matthews and Mitch Marner.

Trading Nazem Kadri

The Nazem Kadri trade is one Shanahan would love to have back. While the trade wasn’t his decision necessarily, the organization felt it was time to move on from Kadri after he had been suspended in back-to-back postseasons.

At the time, the trade looked solid on paper. The Leafs got Tyson Barrie, a bona fide top-pairing blue liner, while the Colorado Avalanche got a second-line center to play behind Nathan Mackinnon.

The deal worked out for Colorado as they went on to win a Stanley Cup in 2022. For Toronto, Barrie failed to live up to expectations, eventually leaving the team for nothing.

Allowing Wiliam Nylander and Mitch Marner's contract negotiations drag on

Both William Nylander and Mitch Marner forced the Maple Leafs’ hand by dragging their latest contract negotiations well into training camp. Nylander’s case was particularly complicated as he signed right before he was ineligible to play that season.

Marner and his camp dragged out their last negotiation in 2019, forcing the team to pony up at the last minute. The same situation repeated this year, with Marner potentially walking away from the team for nothing.

Best decisions

Drafting Auston Matthews was by far the team's best choice - Source: Imagn

Here’s a look at the best decisions during Brendan Shanahan’s tenure

Hiring Craig Berube

No offense to Sheldon Keefe. But the decision to hire Keefe was based more on the recommendation by Kyle Dubas than a genuine search for a coach who matched the team’s identity.

The lack of playoff success prompted the firing of Keefe and the hiring of Craig Berube. Berube turned things around, transforming the Leafs into Atlantic Division winners. While things didn’t work out well in Berube’s first postseason, the overall outcome was solid.

Letting Kyle Dubas go

Kyle Dubas was eager to move up in the hockey world. But it seemed that Shanahan was blocking Dubas’ promotion.

So, Dubas engineered his move to the Pittsburgh Penguins to get the promotion he wanted.

While Dubas’ actions weren’t the most glamorous at the time, the Leafs made the right decision in letting him go. Dubas got his promotion and Shanahan hired Brad Treliving.

Treliving has successfully managed a transition that promises to yield a much better playoff-contending team in the years to come.

Drafting Auston Matthews

Early in Shanahan’s tenure, the Maple Leafs successfully tanked the 2016 season, landing them the first-overall pick.

Auston Matthews was the hands-down first-overall pick that year. Nevertheless, other standout players like Matthew Tkachuk and Patrik Laine seemed enticing choices.

The Leafs played it safe and took Matthews. The move has yielded the team its franchise star. Now, imagine if the Leafs had taken Laine or Pierre-Luc Dubois with that first-overall pick. The universe could have been radically different than it is today.

If the Maple Leafs win a Stanley Cup in the next half-decade or so, Brendan Shanahan should get the credit he deserves for setting up the team on that path.