I still remember the day the Toronto Maple Leafs drafted William Nylander. I was 14 years old, and it was probably the second or third draft I can remember actually sitting down to watch. Everybody and their mother, led notably by Don Cherry, had been banging the drum to bring Peterborough Petes forward Nick Ritchie to Toronto with the eighth overall pick, and I was expecting nothing else at that point. 
The Leafs used their first-round pick the year prior to draft 6-foot-5 two-way forward Frederik Gauthier, and two years before that, they traded up in the first round to select power forward Tyler Biggs. Both pretty terrible decisions in hindsight, but they had a type, and I expected it to be no different in 2014 despite Dave Nonis standing at the podium instead of Brian Burke.
Little did I know, as the “pick is in” graphic came across the television screen, this time it was different. Nonis and the Leafs’ crew made their way to the stage and said the words that would eventually lead us to this very moment and this article. 
“Toronto is proud and happy to select…from MODO…Sweden…William Nylander” 
I was shocked at first. Not disappointed, but definitely shocked. The media and fellow fans alike had spent the past couple of months manifesting Ritchie to Toronto. Size over skill and truculence over talent had been the mantra of the front office. Instead, we were looking at a baby-faced William hugging his father, longtime NHLer Michael Nylander in the stands of Wells Fargo Arena. 
<div class="jetpack-video-wrapper"><iframe loading="lazy" class="youtube-player" width="1424" height="801" src="https://www.youtube.com/embed/_0XAYG7gSHE?version=3&#038;rel=1&#038;showsearch=0&#038;showinfo=1&#038;iv_load_policy=1&#038;fs=1&#038;hl=en-US&#038;autohide=2&#038;wmode=transparent" allowfullscreen="true" style="border:0;" sandbox="allow-scripts allow-same-origin allow-popups allow-presentation allow-popups-to-escape-sandbox"></iframe></div>
All that shock washed away seconds later when TSN listed his NHL player comparable as Patrick Kane. 
In a lot of ways, I think the selection of Nylander signified a change in the direction of the Toronto Maple Leafs. You could argue that the true change in direction began with the hiring of Brendan Shanahan as Team President a few months prior, but the Nylander pick was the first indication that the Leafs were actually planning on doing things differently, for once. 
You can make all the sarcastic remarks about how the Leafs haven’t benefitted whatsoever with the shift in direction of the franchise, and while the playoff success on paper renders that notion true, what they’ve been trying to do for the past decade is still more respectable than the disaster that took place between 2006 and 2016. I would know because 2006 is when I started watching hockey. Look at the Maple Leafs draft classes in that span. Outside of Morgan Rielly and Nazem Kadri, every prospect they drafted either never panned out, or did for another team. 
While fans were mostly on board with the draft pick, from what I remember anyway, some were dead set against it. No way this small, young Swede would fit the Toronto market. Let&#8217;s reflect on the leader of this take: 
<blockquote class="twitter-tweet" data-width="550" data-dnt="true">
Don Cherry ripping on the Leafs for picking William Nylander &gt; Nick Ritchie in the 2014 draft 😅 <a href="https://twitter.com/hashtag/LeafsForever?src=hash&amp;ref_src=twsrc%5Etfw">#LeafsForever</a> <a href="https://t.co/gCHDOEkNjK">pic.twitter.com/gCHDOEkNjK</a>
&mdash; Leafs Papi (@LeafsPapi_) <a href="https://twitter.com/LeafsPapi_/status/1470828782227492866?ref_src=twsrc%5Etfw">December 14, 2021</a></blockquote>
<script async src="https://platform.twitter.com/widgets.js" charset="utf-8"></script>
Nylander was a breath of fresh air for the organization. I’ll never forget that day back in 2016 when he was first called up. The Leafs were in full tank mode at that time, had just unloaded several pieces at the trade deadline, and along with Nylander, recalled prospects Kasperi Kapenen, Zach Hyman, Connor Brown, and Nikita Soshnikov. For the first time all year, I was actually cheering for them to win some games. 
On March 5th, 2016, Nylander scored his first NHL goal on a faceoff win by…Brooks Laich. A moment that marked the start of what would be a great career for the former, and an all-time trivia question for the latter. 
<div class="jetpack-video-wrapper"><iframe loading="lazy" class="youtube-player" width="1424" height="801" src="https://www.youtube.com/embed/e8hgL0PRbKQ?version=3&#038;rel=1&#038;showsearch=0&#038;showinfo=1&#038;iv_load_policy=1&#038;fs=1&#038;hl=en-US&#038;autohide=2&#038;wmode=transparent" allowfullscreen="true" style="border:0;" sandbox="allow-scripts allow-same-origin allow-popups allow-presentation allow-popups-to-escape-sandbox"></iframe></div>
Nylander’s actual rookie campaign, which took place in 2016-17, was somewhat clouded by the arrival of both Auston Matthews and Mitch Marner to the NHL. Matthews was the shiny new toy, fresh off being selected first overall in 2016, and Marner was the token local boy of the new wave of talent. For Nylander to not even be the second-most touted player that year was a welcomed change of pace for the Maple Leafs.
That being said, he still had his moments. He assisted on two of the goals from Matthews’ legendary four-goal debut, scored his first NHL hat trick months later against the Boston Bruins, and finished his rookie season with 61 points in 81 games. He proved that his rookie season wasn’t a fluke the following year, posting the same amount of points in 82 games. 2018-19 is where it got dicey. 
As we crept through the 2018 offseason, more and more days passed without a contract for Nylander. His entry-level deal had expired, and he was in need of a re-up. It was the first true test for Kyle Dubas, who was recently named general manager at the time, and once the 2018-19 season got underway, fans started to grow bitter over the Swede’s holdout. It didn’t help his case with the fans that Kasperi Kapanen had stepped into his role alongside Matthews and was producing well to start the year. As the days went by and they got closer to the December 1st, 5:00 pm cutoff without a contract for Nylander, fans started calling for the Leafs to cut ties with their star and simply let Kapanen run with his momentum (which is precisely why we don’t let fans make decisions). 
Finally, mere minutes before the deadline, the Leafs announced the deal. When I say “mere minutes”, I mean it. I think the exact number was eight minutes before the deadline. Either way, it was close enough that had there been a glitch in the NHL’s contract filing system, they wouldn’t have submitted the terms in time, and he would have had to sit out the year. But, alas, they got it through in time, and it was time for Nylander to come home to Toronto. 
<blockquote class="twitter-tweet" data-width="550" data-dnt="true">
Going home <a href="https://t.co/neccpyfBVz">pic.twitter.com/neccpyfBVz</a>
&mdash; William Nylander (@wmnylander) <a href="https://twitter.com/wmnylander/status/1068995453285539844?ref_src=twsrc%5Etfw">December 1, 2018</a></blockquote>
<script async src="https://platform.twitter.com/widgets.js" charset="utf-8"></script>
At first, things…didn’t go well, to say the least. Nylander already had to win back certain fans who had a bad taste in their mouth from the holdout and to do so, he needed to come back and fire on all cylinders. But, alas, jumping into an NHL season two months into the festivities when everybody else is in mid-season form is much easier said than done. He was a step behind everyone else, and only managed 27 points in 54 games to end the 2018-19 season. Keep in mind that at this point, Matthews and Marner were still on their entry-level contracts. It didn’t look good on him when you took his contract dispute and his immediate performance and stood them next to his counterparts. 
The end of that season and the off-season that followed were hell for Nylander, for lack of a better term. He was feeling the heat from the media, being virtually traded in every other fan proposal on social media, and he was the subject of countless debates between young fans and their grumpy uncles over family dinners. It felt like you were either on his side, or you wanted him out of town with not much of an in-between. 
Now going on six years since that dreadful negotiation process, it’s safe to say Nylander got the last laugh. Sure, it hasn’t come in the form of playoff success yet, but if nothing else, he’s proven that he’s more than just a small, skilled complimentary piece to Matthews and Marner. He came back strong in 2019-20, scoring 31 goals and finishing with 59 in 68 games before the league was shut down due to the pandemic. He produced at the same clip during the COVID-shortened season, with 41 points in 51 games. And he’s continued to get better and better since then. 
He scored 34 goals, a new career high, in 2021-22, and touched 80 points for the first time in his career. Last season, he hit the 40-goal mark despite always being known as a pass-first type of player and crossed the point-per-game mark for the first time in his career with 87 points in 80 games. 
Okay, okay, we get it. Nylander’s gotten better and hasn’t shown any signs of regression. Surely he’s going to keep producing at that clip of just over a point-per-game and won’t increase his pace of production by 40 points.
Oh, wait. 
That’s officially where we stand in 2024. Nylander is leading the Maple Leafs in points with 21 goals and 54 points in 37 games. He’s tied with Connor McDavid at fifth in the entire league in points, and there have been no words to describe his 2023-24 season besides “rockstar”. He decided to open the season by casually setting a franchise record (yes…THAT 107-year-old franchise) of consecutive games with a point to open the season, with 17. After that streak ended, he went three games without a point and then started up another point streak of 13, with 21 through that span.
<blockquote class="twitter-tweet" data-width="550" data-dnt="true">
All smiles 🥹<a href="https://twitter.com/hashtag/NHLAllStarVote?src=hash&amp;ref_src=twsrc%5Etfw">#NHLAllStarVote</a>  William Nylander <a href="https://t.co/ll59LRq3wQ">pic.twitter.com/ll59LRq3wQ</a>
&mdash; Toronto Maple Leafs (@MapleLeafs) <a href="https://twitter.com/MapleLeafs/status/1744430819299524808?ref_src=twsrc%5Etfw">January 8, 2024</a></blockquote>
<script async src="https://platform.twitter.com/widgets.js" charset="utf-8"></script>
You can have all the qualms you want about the dollar value he signed for. In reality, $11.5 million annually for the next eight years is a lot of money, and probably too much. But you have to hand it to Nylander. He bet on himself, elected not to sign his contract in the offseason, and now he’s reaping the rewards for it. Is it reasonable to believe he’s going to score at a 120-point pace for the rest of his career? Probably not. But he’s continued to get better and better each year since his initial contract holdout, and at this point, there’s more reason to believe he’s closer to the player he’s been the past few years as opposed to anything else. 
What also makes Nylander worth the money on his contract is the fact that he has the perfect mindset for this specific market. We’ve seen in the past that not everybody can handle the heat of the kitchen that is Toronto sports. But, not only did he survive getting dragged for his contract holdout, he did so with a smile on his face and came back even better. You can see in his body language when talking to the media that he doesn’t have a single thought in between his ears. Radio host tries to put together a mock trade package sending him to Anaheim for Nick Ritchie and Brandon Montour? Non-issue. Remember when one columnist, who shall remain nameless, wrote a weird article comparing him to IKEA furniture that had come without instructions? Again, non-issue. 
<blockquote class="twitter-tweet" data-width="550" data-dnt="true">
TORONTO SUN FRONT: No second-line production? No real hope for the Maple Leafs from <a href="https://twitter.com/simmonssteve?ref_src=twsrc%5Etfw">@simmonssteve</a>: <a href="https://t.co/oYGC3DZfbK">https://t.co/oYGC3DZfbK</a> <a href="https://t.co/QAq7tyR6ek">pic.twitter.com/QAq7tyR6ek</a>
&mdash; Toronto Sun (@TheTorontoSun) <a href="https://twitter.com/TheTorontoSun/status/1362011643731935232?ref_src=twsrc%5Etfw">February 17, 2021</a></blockquote>
<script async src="https://platform.twitter.com/widgets.js" charset="utf-8"></script>
I recognize at my age, 24 years old if you were curious, I was never around to bask in the glory days of Wendel Clark, Doug Gilmour, and the prime of Mats Sundin. Nylander probably holds more value to me because I was forced to watch bottom-of-the-barrel Leafs teams that were put together with used bandaids. There was no salary cap back then, and from what I gather from talking to older fans, that was the time to be a fan. Whenever the Leafs made an acquisition or signed a player long-term, there were no reservations about a couple hundred thousand dollars. There was just one question; who is this and how does he improve my favourite team? 
It’s unfortunate that the salary cap has impeded our ability to appreciate players for their talent, which is precisely why I’m not going to be spending any time fretting about the money on his deal. The cap will rise, other players will either leave or take discounts to stay (looking at you, John Tavares), and Nylander’s annual income is going to be an afterthought next time he scores a big goal. And, regardless of what you think of how much he makes and how the Leafs have spread out their money, it&#8217;s refreshing to have a pair of stars in Nylander and Morgan Rielly who are willing to be lifelong Maple Leafs. That&#8217;s not a shot at Matthews, who recently re-upped for four years with the Leafs, or Marner, who has his own contract negotiations coming up this summer. But as somebody who watched the Leafs ice a team of temporary fixes for my first ten years watching the team, it&#8217;s cool to see legitimate star players want to spend their entire career here. 
When talking to the media afterward, he said that winning a Cup in Toronto would be the “ultimate dream”. Let’s see if he can add that accolade to his resume at some point over the next eight years.

I still remember the day the Toronto Maple Leafs drafted William Nylander. I was 14 years old, and it was probably the second or third draft I can remember actually sitting down to watch. Everybody and their mother, led notably by Don Cherry, had been banging the drum to bring Peterborough Petes forward Nick Ritchie to Toronto with the eighth overall pick, and I was expecting nothing else at that point. 

The Leafs used their first-round pick the year prior to draft 6-foot-5 two-way forward Frederik Gauthier, and two years before that, they traded up in the first round to select power forward Tyler Biggs. Both pretty terrible decisions in hindsight, but they had a type, and I expected it to be no different in 2014 despite Dave Nonis standing at the podium instead of Brian Burke.

Little did I know, as the “pick is in” graphic came across the television screen, this time it was different. Nonis and the Leafs’ crew made their way to the stage and said the words that would eventually lead us to this very moment and this article. 

“Toronto is proud and happy to select…from MODO…Sweden…William Nylander” 

I was shocked at first. Not disappointed, but definitely shocked. The media and fellow fans alike had spent the past couple of months manifesting Ritchie to Toronto. Size over skill and truculence over talent had been the mantra of the front office. Instead, we were looking at a baby-faced William hugging his father, longtime NHLer Michael Nylander in the stands of Wells Fargo Arena. 

https://www.youtube.com/watch?v=_0XAYG7gSHE

All that shock washed away seconds later when TSN listed his NHL player comparable as Patrick Kane. 

In a lot of ways, I think the selection of Nylander signified a change in the direction of the Toronto Maple Leafs. You could argue that the true change in direction began with the hiring of Brendan Shanahan as Team President a few months prior, but the Nylander pick was the first indication that the Leafs were actually planning on doing things differently, for once. 

You can make all the sarcastic remarks about how the Leafs haven’t benefitted whatsoever with the shift in direction of the franchise, and while the playoff success on paper renders that notion true, what they’ve been trying to do for the past decade is still more respectable than the disaster that took place between 2006 and 2016. I would know because 2006 is when I started watching hockey. Look at the Maple Leafs draft classes in that span. Outside of Morgan Rielly and Nazem Kadri, every prospect they drafted either never panned out, or did for another team. 

While fans were mostly on board with the draft pick, from what I remember anyway, some were dead set against it. No way this small, young Swede would fit the Toronto market. Let's reflect on the leader of this take: 

https://twitter.com/LeafsPapi_/status/1470828782227492866

Nylander was a breath of fresh air for the organization. I’ll never forget that day back in 2016 when he was first called up. The Leafs were in full tank mode at that time, had just unloaded several pieces at the trade deadline, and along with Nylander, recalled prospects Kasperi Kapenen, Zach Hyman, Connor Brown, and Nikita Soshnikov. For the first time all year, I was actually cheering for them to win some games. 

On March 5th, 2016, Nylander scored his first NHL goal on a faceoff win by…Brooks Laich. A moment that marked the start of what would be a great career for the former, and an all-time trivia question for the latter. 

https://www.youtube.com/watch?v=e8hgL0PRbKQ

Nylander’s actual rookie campaign, which took place in 2016-17, was somewhat clouded by the arrival of both Auston Matthews and Mitch Marner to the NHL. Matthews was the shiny new toy, fresh off being selected first overall in 2016, and Marner was the token local boy of the new wave of talent. For Nylander to not even be the second-most touted player that year was a welcomed change of pace for the Maple Leafs.

That being said, he still had his moments. He assisted on two of the goals from Matthews’ legendary four-goal debut, scored his first NHL hat trick months later against the Boston Bruins, and finished his rookie season with 61 points in 81 games. He proved that his rookie season wasn’t a fluke the following year, posting the same amount of points in 82 games. 2018-19 is where it got dicey. 

As we crept through the 2018 offseason, more and more days passed without a contract for Nylander. His entry-level deal had expired, and he was in need of a re-up. It was the first true test for Kyle Dubas, who was recently named general manager at the time, and once the 2018-19 season got underway, fans started to grow bitter over the Swede’s holdout. It didn’t help his case with the fans that Kasperi Kapanen had stepped into his role alongside Matthews and was producing well to start the year. As the days went by and they got closer to the December 1st, 5:00 pm cutoff without a contract for Nylander, fans started calling for the Leafs to cut ties with their star and simply let Kapanen run with his momentum (which is precisely why we don’t let fans make decisions). 

Finally, mere minutes before the deadline, the Leafs announced the deal. When I say “mere minutes”, I mean it. I think the exact number was eight minutes before the deadline. Either way, it was close enough that had there been a glitch in the NHL’s contract filing system, they wouldn’t have submitted the terms in time, and he would have had to sit out the year. But, alas, they got it through in time, and it was time for Nylander to come home to Toronto. 

https://twitter.com/wmnylander/status/1068995453285539844

At first, things…didn’t go well, to say the least. Nylander already had to win back certain fans who had a bad taste in their mouth from the holdout and to do so, he needed to come back and fire on all cylinders. But, alas, jumping into an NHL season two months into the festivities when everybody else is in mid-season form is much easier said than done. He was a step behind everyone else, and only managed 27 points in 54 games to end the 2018-19 season. Keep in mind that at this point, Matthews and Marner were still on their entry-level contracts. It didn’t look good on him when you took his contract dispute and his immediate performance and stood them next to his counterparts. 

The end of that season and the off-season that followed were hell for Nylander, for lack of a better term. He was feeling the heat from the media, being virtually traded in every other fan proposal on social media, and he was the subject of countless debates between young fans and their grumpy uncles over family dinners. It felt like you were either on his side, or you wanted him out of town with not much of an in-between. 

Now going on six years since that dreadful negotiation process, it’s safe to say Nylander got the last laugh. Sure, it hasn’t come in the form of playoff success yet, but if nothing else, he’s proven that he’s more than just a small, skilled complimentary piece to Matthews and Marner. He came back strong in 2019-20, scoring 31 goals and finishing with 59 in 68 games before the league was shut down due to the pandemic. He produced at the same clip during the COVID-shortened season, with 41 points in 51 games. And he’s continued to get better and better since then. 

He scored 34 goals, a new career high, in 2021-22, and touched 80 points for the first time in his career. Last season, he hit the 40-goal mark despite always being known as a pass-first type of player and crossed the point-per-game mark for the first time in his career with 87 points in 80 games. 

Okay, okay, we get it. Nylander’s gotten better and hasn’t shown any signs of regression. Surely he’s going to keep producing at that clip of just over a point-per-game and won’t increase his pace of production by 40 points.

Oh, wait. 

That’s officially where we stand in 2024. Nylander is leading the Maple Leafs in points with 21 goals and 54 points in 37 games. He’s tied with Connor McDavid at fifth in the entire league in points, and there have been no words to describe his 2023-24 season besides “rockstar”. He decided to open the season by casually setting a franchise record (yes…THAT 107-year-old franchise) of consecutive games with a point to open the season, with 17. After that streak ended, he went three games without a point and then started up another point streak of 13, with 21 through that span.

https://twitter.com/MapleLeafs/status/1744430819299524808

You can have all the qualms you want about the dollar value he signed for. In reality, $11.5 million annually for the next eight years is a lot of money, and probably too much. But you have to hand it to Nylander. He bet on himself, elected not to sign his contract in the offseason, and now he’s reaping the rewards for it. Is it reasonable to believe he’s going to score at a 120-point pace for the rest of his career? Probably not. But he’s continued to get better and better each year since his initial contract holdout, and at this point, there’s more reason to believe he’s closer to the player he’s been the past few years as opposed to anything else. 

What also makes Nylander worth the money on his contract is the fact that he has the perfect mindset for this specific market. We’ve seen in the past that not everybody can handle the heat of the kitchen that is Toronto sports. But, not only did he survive getting dragged for his contract holdout, he did so with a smile on his face and came back even better. You can see in his body language when talking to the media that he doesn’t have a single thought in between his ears. Radio host tries to put together a mock trade package sending him to Anaheim for Nick Ritchie and Brandon Montour? Non-issue. Remember when one columnist, who shall remain nameless, wrote a weird article comparing him to IKEA furniture that had come without instructions? Again, non-issue. 

https://twitter.com/TheTorontoSun/status/1362011643731935232

I recognize at my age, 24 years old if you were curious, I was never around to bask in the glory days of Wendel Clark, Doug Gilmour, and the prime of Mats Sundin. Nylander probably holds more value to me because I was forced to watch bottom-of-the-barrel Leafs teams that were put together with used bandaids. There was no salary cap back then, and from what I gather from talking to older fans, that was the time to be a fan. Whenever the Leafs made an acquisition or signed a player long-term, there were no reservations about a couple hundred thousand dollars. There was just one question; who is this and how does he improve my favourite team? 

It’s unfortunate that the salary cap has impeded our ability to appreciate players for their talent, which is precisely why I’m not going to be spending any time fretting about the money on his deal. The cap will rise, other players will either leave or take discounts to stay (looking at you, John Tavares), and Nylander’s annual income is going to be an afterthought next time he scores a big goal. And, regardless of what you think of how much he makes and how the Leafs have spread out their money, it's refreshing to have a pair of stars in Nylander and Morgan Rielly who are willing to be lifelong Maple Leafs. That's not a shot at Matthews, who recently re-upped for four years with the Leafs, or Marner, who has his own contract negotiations coming up this summer. But as somebody who watched the Leafs ice a team of temporary fixes for my first ten years watching the team, it's cool to see legitimate star players want to spend their entire career here. 

When talking to the media afterward, he said that winning a Cup in Toronto would be the “ultimate dream”. Let’s see if he can add that accolade to his resume at some point over the next eight years.

William Nylander: From prospect scapegoat to 92 million dollar man

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