The mystery of the funniest Maple Leaf: How Connor Dewar won over his teammates

Steven Lorentz begins the discussion about Connor Dewar with a challenge: Get him to open up.

Dewar, after all, is a Maple Leafs teammate who can appear to be in pain when communicating with the media; a player who scowls or, as Lorentz describes it, mean mugs, when photographed.

Not much is known about Dewar outside the Leafs room.

And he seems happy to keep it that way.

Will probably look at this for the rest of the year pic.twitter.com/wLfYcdFJyp Toronto Maple Leafs (@MapleLeafs) December 31, 2024 Youve got to try and crack him, Lorentz says.

Hes mysterious.

As I turn my attention to Dewar, he crosses his arms and smiles.

Yeah, good luck with that, the Leafs forward deadpans, his voice barely growing above a whisper.

He sounds less like a professional hockey player and more like Jerry Seinfeld at his sarcastic best.

Advertisement Walking away, Lorentz grins and pats me on the shoulder.

Months earlier, Lorentz was the first player surveyed for our 2024-25 Leafs player poll ( part one / part two ).

When asked which teammates he would prefer to be trapped in an elevator with, his first answer was immediate: Dewar.

It caught me off guard.

Since Dewar arrived in Toronto at last seasons trade deadline, weve learned very little about the pesky and energetic bottom-six forward.

My surprise was amplified when Dewar ended up tying gregarious teammate Morgan Rielly as the top vote-getter in the category.

Dewars personality doesnt jump out in the room like Riellys.

He doesnt dominate the headlines with his quotes like Ryan Reaves .

Hes not as affable and lighthearted as William Nylander .

What were we missing? Why do the Leafs adore and heap attention on a teammate who, from the outside, seems to want no attention whatsoever? Just pure entertainment all the time, Reaves says.

Ian Walker had never been to Everett, Wash.

when he arrived as a fresh-faced 16-year-old to begin his major junior hockey career.

The defenceman was placed into a billet house with Dewar, who had already logged a season in Everett.

Dewar didnt exactly start the relationship by offering a tour of the surroundings.

The first few days, he was an enigma, Walker says.

Trust does not come immediately from Dewar.

Conversations were brief, if they occurred at all.

Part of it is because I grew up in a small town, Dewar says of The Pas in northern Manitoba, population 7,302.

For the first 15 years of my life, I only saw the same five or six friends every day.

Quietly through the start of their first season together, Walker wondered: Was he ever going to get to know his roommate? It took time, but a friendship evolved through what Walker calls shared experiences.

Advertisement Dewars game is built on effort.

Once he saw that same kind of effort from teammates he didnt know, he became comfortable sharing his personality.

Hes a guy who battles when he plays.

And the more we played together, the more mutual respect we had for each other, Walker says.

Dewar attributes his attitude and his role to growing up in what Dewar calls a secluded, northern community.

Everyone takes pride in their work.

I saw it every day with my dad getting up and going to work at the mill.

You grow to admire it, he says.

And so when his teammates worked, Dewar grew to admire them as well.

That meant letting them into his world a place built on snark and quick wit.

Dewar says he gets his sense of humour from his witty and quick father Jade.

Growing up with that kind of humour in his life meant Dewar, in his estimation, looks at the world through that lens.

I dont take anything too seriously.

What you dont see is how hes always trying to play pranks on people, Walker says.

After their awkward first months, Walker says it wouldnt be a surprise for the teenaged Dewar to have messed up his bedsheets almost daily.

Dewar then might crack a quick joke in Walkers ear to get him laughing unprompted and uncontrollably in front of his teammates.

Years later, Dewar invited Walker on the Leafs January mentors trip.

He wanted to have his old friend by his side.

(Dewar) has a hard exterior shell, but hes a softie on the inside, Walker says.

When Dewar arrived in Toronto, that shell grew thick.

First, he had to get over the shock of his first -ever trade.

Dewar played with the same team through four years of junior hockey and spent his first two professional seasons firmly planted in Iowa with the Minnesota Wild s AHL team before beginning a two-and-a-half-year stint in the NHL .

Advertisement Id been fortunate that way, Dewar says.

Because he was comfortable in the Wild organization, teammates saw the real Dewar.

Unless youre in his inner circle, you dont really see too much, former Wild teammate Zach Bogosian says.

But Dewars inner circle grew in Minnesota.

So, too, did the laughs.

Hes one of those guys who is quiet and then hell just drop a zinger out of nowhere.

Youd never think it would be coming from him.

Its always the loud guys who have the zingers, Bogosian says.

Dewars blue-collar upbringing, Bogosian figured, helped make him one of the funniest teammates.

Generally people like that have a good temperature with social skills, Bogosian says of teammates with blue-collar pasts.

The way (Dewars) personality is, he takes everything in, studies the situation, really thinks about it then hell really lay down the hammer.

Arriving in Toronto on trade deadline day last season meant Dewar didnt want to step on any toes in the Leafs dressing room.

He kept his biting sense of humour to himself.

One might assume that Dewars offseason surgery to repair a torn labrum would have prevented him from relaxing around his new team.

But it was the months Dewar spent around the Leafs staff through the summer and training camp, day after day, during his recovery that helped him.

My thing is once I get comfortable in a place, I can start to open up ...

and show who I am, Dewar says.

Dewar has been out of the lineup for more than a week with an injury.

Before that, he was enjoying a strong season.

The offence might not have been there.

But the speed, tenacity and defensive reliability were.

He had found a role on the Leafs.

Everyone has a lot of respect for the way (Dewar) plays, Fraser Minten says.

He works as hard as he can every single game.

A guy you want on your team, Minten added before a wry smile emerged, and in the locker room, too.

Advertisement And so when his Leafs teammates arrived this season, they saw a different side of Dewar emerge.

Its a big market and its different than having, like, three guys walking in to do interviews, Reaves says of Dewar getting comfortable in Toronto.

But he comes out of his shell at the right time.

When he comes out, its hilarious.

Dewar, teammates say, doesnt have to reach deep to find sarcasm in any situation.

In an industry built on ego and in which players often attempt to prove themselves by making a booming first impression, Dewar strays from the path.

Whenever (Dewar) is speaking, its something funny, Minten says.

Hes always quiet until his one-liners.

Once he gets one teammate laughing, everyone else wants in.

His sarcasm, his mannerisms, his quick one-liners: Hes the full package of being funny on the spot, Reaves says of Dewar.

A strong team off the ice is comprised of many balanced roles: calming veterans, social butterflies, strong and silent types and the subjects of jokes.

It turns out the Leafs want to be around Dewar because hes carved out his off-ice role as the one delivering those jokes.

The funniest kid, Matthew Knies says of Dewar.

His timing is impeccable.

This is the same Dewar who at 14 was forced to leave his remote northern upbringing for stronger hockey challenges.

Chided about his upbringing in The Pas, Dewar confidently told a teammate: Theres North, East, West and Soft.

(Dewar) is a Western (Hockey) League beauty.

You can write that, Minten says.

He makes everybody laugh in their own way.

Take Dewars description of his new puppy, a Basset Hound named Ringo.

What led to the name? After Ringo Starr, Dewar deadpans again with pinpoint comedic timing in his pause.

...

You know, of the Beatles.

As if one would need reminding of a cultural touchstone.

Sure enough, I chuckle.

Advertisement His favourite movies? The Other Guys, Step Brothers and Pineapple Express.

Theres a theme here, as well as a clearer sense of what informs Dewars celebrated sense of humour.

Hes big on inside jokes, Walker says.

I keep digging.

Dewar strikes me as someone who might enjoy Vince Vaughns oft-sarcastic humour.

Is he a fan? Overexcited human, Dewar quickly says of the actor.

His response makes me laugh again.

As I do, more of Dewars teammates walk by and grin.

You laugh before he even says anything, Knies says of Dewar, because you know its going to be funny.

Toward the end of our conversation, Dewar is opening up.

He tells me that as punishment for finishing last place in his fantasy football league, he was going to have to deliver a comedy routine in front of his friends.

Hes terrified, he says, but he was still busy putting together material anyway.

Thankfully for Dewar, he got the necessary bounces and finished second last.

But his Leafs teammates still want to hear from him.

When the season grows long, his quick wit from the back of the class can deflate tense situations.

Watching the way his teammates faces light up when asked about him makes it clear: when the spirit in the Leafs room is high, Dewar likely deserves some credit.

Walker is not surprised by Dewars growing role with his team in Toronto.

It might have taken Walker most of those three seasons to get the real Dewar in his life.

But over five years later, he still cant get enough.

(Dewar) doesnt want to be in the spotlight, but he does want to mess with you, Walker says.

Thats his way of bringing you in and making you feel closer to him.

Thats something his Leafs teammates have clearly learned and embraced in the 11 or so months since his arrival.

(Top photo: Mark Blinch / NHLI via Getty Images).

This article has been shared from the original article on theathleticuk, here is the link to the original article.