Brendan Shanahan faces toughest challenge with Toronto Maple Leafs

The Toronto Maple Leafs have decided to keep Team President Brendan Shanahan around for another six years. His biggest challenge now is assembling a team that cannot only make, but compete, in the playoffs.

Toronto Maple Leafs fans are once again disappointed by their team’s first round exit at the hands of the Boston Bruins. It’s easy to understand their frustration, especially considering this is the second year in a row their team has met the same fate by the same team. Considering where they were a few short seasons ago without Brendan Shanahan, they should be also be thrilled with the result.

Shanahan took over as president of the Maple Leafs at the end of the 2015 season. In his post-playing career, perception of him had been a mixed bag up to that point. Shanahan was most notably the butt of jokes and faced criticism of the overbearing penalties he handed out as head of the Department of Player Safety.

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His tenure with the Maple Leafs has been nothing short of successful. When Shanahan was handed the reigns, the Leafs were a once proud franchise that had hit rock bottom of mediocrity. Team owners committed to a rebuild, which they expected to endure five more seasons of losing in what was dubbed a “scorched Earth” rebuild.

Shanahan spent the first year at his new post sitting idle, aside from the coaching hire of Mike Babcock. However, after winning the 2016 draft lottery and drafting Auston Matthews, the rebuild got accelerated and the Leafs have made the playoffs in every season since then.

The Leafs have recognized Shanahan’s efforts by giving him a six-year contract extension. He will spend the next six years presiding and making decisions for a much different team than he inherited.

Add the fact that general manager Kyle Dubas, who spent the first part of Shanahan’s tenure growing into his position, is finally settled in with a string of successes, and the Leafs seem ready to take that next step.

Prior to Shanahan’s arrival, Toronto had only seen one playoff appearance in 11 seasons. Even though they’ve achieved three straight playoff appearances in the Shanahan-Mathews era, all three have been first-round exits. He has already built a winning team, now it’s time for him to build a winning team.

The Maple Leafs haven’t won a playoff series since 2004, which was also their last playoff appearance before the 2013 lockout.

You can argue the Leafs have a young core between Mitch Marner and Mathews, their defense is holding them back, and that the biggest free agent acquisition in their history, John Tavares, lacks playoff experience due to his former life on a success-eluding New York Islanders team.

No matter how well you can make those arguments, it doesn’t get rid of the fact the Leafs also signed veteran player Patrick Marleau who came to Toronto with a ton of playoff experience. Then there’s Babcock, who has seen more playoff hockey than almost every other current NHL coach. And after three straight appearances, there’s no justifiable reason the “lack of playoff experience” excuse still applies.

The Leafs didn’t live up to expectations this past season, in which they were the early odds on favorites to win the Stanley Cup after the Tavares signing. Saying “how can this team succeed in the playoffs” is a very broad question. Babcock can simplify that for himself by asking “how can this team beat the Bruins?”

Curtis Rush is a sports reporter for Forbes who gave his own insight on why Toronto, once again, lost to Boston in the playoffs first round. What makes Rush’s insight unique is that he looks at Toronto’s defeat from both a hockey analysis standpoint and the current front office and business situation of the Leafs a whole.

It’s easy to blame the Leafs game seven loss on poor defensive play and goaltender Frederik Andersen, but Rush points out the bigger problems of lack of team chemistry and lack of opportunistic chances. While it’s easy to use the excuse “they didn’t play as a team”, Rush points out specific examples from throughout the series backing his claim.

"Ten of their 17 goals came not because of great passing. They came on tips, rebounds, shots from the point, nice individual shots, an empty netter or penalty shot.Seven goals came on pretty passing combinations, but three were on the power play and only two were off the rush."

Meanwhile, the Bruins have made it this deep in the playoffs, and are currently dominating the Hurricanes, because of their balanced play that’s overwhelming and suffocating to their opponents. Rush then goes on to explain how the lack of team chemistry hurt the Leafs and how they could have capitalized on opportunistic chances.

"Eight Bruins goals came on pretty passing plays, most of them with the man advantage.Only five goals came on point shots or rebounds.Four goals came on Maple Leaf turnovers, while Boston played a much cleaner game in front of their net."

As soon as rush pointed out the lack of team chemistry, the perfect example that came to mind was William Nylander’s early year contract standoff. Hockey is a business, and that’s understandable that the young player would want a better contract.

But missing half of a playing season is a different story that shows Nylander entered the Maple Leafs locker room with a “what is this doing for me” mindset instead of a team-first one.

Nylander’s contract saga goes hand in hand with another interesting aspect from Rush’s Forbes article – this season was the last season that Mathews and Marner were on entry-level deals. Although Mathews has signed a largely team friendly extension, that doesn’t prevent all the cap problems the Leafs are sure to face.

Leafs fans could all sit around and point to the usual suspects of saying that they need better defense (which they do), maybe better goaltending (which is arguable, but not a point I’m 100% sold on), or a new coach.

No matter how much Shanahan and Dubas try to duct tape those problems, they’re only playing on borrowed time by prolonging the eventual cap crunch they’ll have to endure. It’s not unsimiliar to what Chicago experienced after the 2010 cup run, and although cap management might win Toronto a cup the same way adding Erik Karlsson (don’t get your hopes up Leaf fans) to their blue line might, lack of it could cost them the chance at a cup later.

As for the team chemistry part, there’s no quick fix in that end. If the Leafs end up going up against the cap and difficult decisions need to be made, that problem is bound to get worse. While firing Babcock may not seem like the most reasonable choice, his coaching with Toronto has been a shadow of his coaching from Detroit’s glory years.

Usually, lack of team chemistry is a problem that starts with an unmotivating coach. Looks like all the pieces are in place for Shanahan to at least take a long hard look at letting Babcock go.

Shanahan succeeded in his mission to make the Leafs a successful team once again, but now it’s time for them to take the next step. Toronto is getting impatient for playoff success. A good front office can never think too far ahead, and even though it may be premature to think about the 2020 playoffs, the Maple Leafs are entering with a lot more questions than answers.