As we embark on our annual TLN Top 20 Prospects series, it’s important to remember and recognize the special players that paved the way for tomorrow’s stars. Over the next few weeks, we will be announcing our first ever TLN All-Time Greatest Leafs Team, announcing a new player every day until we’ve filled out our 23-man roster.  

It’s been a crazy few weeks, as we’ve combed through some of the greatest players in Leafs history to create an all-time team. We’ve spanned decades upon decades, going as far back as the 20’s and 30’s to grab the likes of Babe Dye and Charlie Conacher. Our goaltending rotation ranges from the present age of 44 to 89. The team’s centre depth is about as good as it gets for any potential team; off the top of my head, only Montreal, Detroit, and Pittsburgh could definitely claim better options down the middle.

But we’re still missing one more player on the wing. A top six winger, no less. While many will surely disagree with the selection, I don’t think there’s a better player left to choose than the recently departed Phil Kessel.

Kessel joined the Leafs in one of the most controversial trades of the modern era, as Brian Burke sent two first round picks and a second rounder to the Boston Bruins for the 21-year-old sniper. As we all know, Burke grossly over-estimated the talent level of his team (Mike Komisarek and Jeff Finger were not helping their cause), and the team crashed and burned, but the Bruins managed to turn Tyler Seguin, Dougie Hamilton, and Jared Knight into a bucket of hot ooze anyway.

You could see why Burke wanted to take the risk, though – Kessel had picked up a 36 goal season and point-per-game playoff in sheltered minutes, albeit with a great centre in Marc Savard. While he didn’t immediately repeat that pace, Kessel began to make an impact relatively quickly. Though he missed the first twelve games of the 2009/10 while recovering from shoulder surgery, he went on to lead the team in goals and points, a trend that continued throughout his career in blue and white.

In his time here, Kessel put up some great numbers, no matter which way you slice it. Compared to the rest of the league in the same stretch, Kessel played the 23rd most games and currently holds the League’s fifth-longest ironman streak. He scored more goals than anybody other than Alex Ovechkin, Corey Perry, and Rick Nash. He was top-ten in points across the league, and still remains near the top when adjusting for a per-game basis. This is all while spending the majority of his time with either John Mitchell, Matt Stajan, or Tyler Bozak down the middle, and whichever left winger happened to be healthy at the time.

Using Hockey-Reference’s era adjusted numbers also works out in his favour. I crunched the numbers before the start of last season, and as it turns out, Kessel led all Leafs wingers all-time in adjusted points per season. To make up for the short stretch in prime age, I turned it into the best five-year burst, but at that point, he still was better than every winger the Leafs have had other than Charlie Conacher.

While Kessel wasn’t the best defensive forward by any stretch of the imagination, he was definitely Toronto’s premier offensive winger, in our own generation and in most others. 

I don’t know if you have an hour to watch Phil Kessel be really awesome at hockey, but if you do, you should probably watch this video. There’s just too many pretty goals to isolate a couple.

Phil has had his share of off-ice moments, be it disgruntlement, admiration for cookies, or general shyness. I’ve picked this one as my favourite though because he backs up his disdain for a really stupid question by not only calling the reporter (who most of us know, but we’ll skip mentioning), but sticking up for his teammates in the process. It was a rare look at him having the team’s back “in the room”, and perhaps came a little too late to shake his reputation, but it was still great to see.

It’s hard to say what Kessel’s legacy will be, given that he’s only been away from the Leafs for two months and is yet to play his first game as a Pittsburgh Penguin. But it’s safe to say that, despite all the spectacular play, he’ll be remembered as a “what if” or a “wasted opportunity”.

His biggest critics will be asking the questions that fit the narratives. What if he was a little less introverted? What if he was in the gym more? What if he was more defensively responsible? What if the trade never happens? They’ll say he wasted his body, and wasted his opportunity to care. They’ll say Brian Burke wasted a rebuild.

His biggest fans will be doing the same. What if the Toronto Media laid off his case? What if he played with Mikhail Grabovski or Nazem Kadri more often? What if the Leafs were able to build a playoff team around him for more than a week and a half? They’ll say that his talents were wasted while being surrounded by garbage.

The answer is likely somewhere down the middle. I’ve never been one to question his conditioning (he did play 446 consecutive games and skates faster than most of the league), but maybe some more time working on his body helps him get an additional step. Great players don’t need great teammates, but they could have probably have found him better support. I’ll always be curious as to the effect that Mike Babcock could have had on him; it would be either super beneficial, or super damaging.

But I guess we’ll never know. Phil Kessel leaves this team with a presently polarizing legacy – he’s the kid from Wisconsin who came in just wanting to play a little bit of hackey, before going home to watch some television while eating a snack. He was a man who never really took himself too seriously, to an extent that tarnished his reputation. He was the closest thing the NHL had to an average joe who also happened to be an elite talent. It’s up to you to decide whether that description is for better, or worse, but one thing’s for sure – nobody who wore blue in white in this disaster of a decade was as exciting to watch with the puck as Phil Kessel.

Few ever have been.