

Randy Carlyle attempts to remember

what a smile feels like

Almost six years ago, the Maple Leafs were in a bad place. They'd missed the playoffs for a team record three straight years. The Muskoka Five situation had just unfolded. They'd fired John Ferguson Jr., but failed in their efforts to lure Brian Burke out of Anaheim. And fans were starting to wonder: Is this the worst it's ever been?

So I decided to find out. In what would go on to become one of the most popular set of posts from this blog's first year, I went back to 1983 and reviewed a quarter century of Maple Leafs misery, assigning a "How bad was it?" score to each season.

The conclusion: Yes, it really was the worst that it had ever been. With a final score of 95/100, the just-completed 2007-08 season took the crown as the worst in recent Leafs history.

But that was a long time ago. In the years since, I've often heard from fans wanting to know when I'd update the series with entries from the Burke/Nonis era. I always figured I'd know when the time was right. Today, with news of Randy Carlyle's contract extension, I think that time has arrived.

And so, six seasons later, it's time for the sequel. Welcome to part four, as we try to answer the question: Is this the worst it's ever been?

2008-09

The good: The Leafs fail to hire a GM during the summer like they said they would, and head into the season with Cliff Fletcher still in charge. But it turns out to be all part of a master plan, as Brian Burke mysteriously becomes available a month into the season and is hired after all. He gives an entertaining press conference that introduces the word "truculence" to the sports world, and eventually has his own guys in place, like Ron Wilson and Dave Nonis. He also outbids Ottawa for college free agent Tyler Bozak, who projects as a possible third-liner someday.

The bad: Before Burke arrives, Fletcher makes a series of odd moves, like trading up to draft Luke Schenn, signing Jeff Finger and trading away Alex Steen. He also fails to get anything for Mats Sundin's negotiating rights, and gives the Habs a second round pick for some punk kid named Mikhail Grabovski.

The team struggles through another non-playoff year, finishing last in the Northeast while leading the NHL in goals allowed. Jason Blake is the team's leading scorer. The goaltending, led by Vesa Toskala and Curtis Joseph, is terrible. Burke should probably get to work on fixing that.

Sundin eventually signs with the Canucks, then comes back to Toronto and beats the Leafs with a shootout-winning goal. It's pretty much the highlight of the season.

How bad was it? 75/100. The team is terrible, but at least Burke seems to have a plan. For the first time in years, there's a palpable feeling of hope.

2009-10

The good: The Leafs draft Nazem Kadri, leading to one of the great draft floor moments of all time. In September, Burke trades three draft picks to the Bruins for Phil Kessel. Despite missing the first month, Kessel scores 30 goals andeveryone agrees that the deal will be a good one for the Leafs as long as the draft pick doesn't end up being unexpectedly high, like tenth.

Later in the season, Burke acquired Dion Phaneuf in exchange for a handful of spare parts, and also manages to somehow offload both Toskala and Jason Blake's contract.

The bad: Burke signs a ton of free agents, pretty much all of whom are expensive busts. The team loses its first eight games and is basically eliminated from the playoffs by Halloween. Toskala and rookie Joasn Gustavsson provide the team with almost historically bad goaltending, and as the season wears on, it becomes apparent that the Leafs could finish dead last and hand the Bruins the #1 overall pick. They avoid that, narrowly, but finish 29th instead.

How bad was it? 90/100. Just an awful year. Among the many, many awful elements of this season was the nagging feeling that Burke wasn't as smart as we'd all hoped he was, and the next few years was just going to be more of the same. But the Phaneuf trade inspired just enough confidence to keep this year out of "worst ever" contention.

2010-11

The good: The offseason is mostly quiet, although the Leafs do add Kris Versteeg and Clarke MacArthur, the latter on a discount deal. Phaneuf is named captain, and immediately starts futzing with the volume on the dressing room stereo. Avoiding a repeat of the previous season's disastrous start, the Leafs win their first four games.

Kessel scores 30 again, and the MacArthur/Grabovski/Nikolai Kulemin line is excellent. An unheralded rookie goalie named James Reimer appears and wins the starting job, giving the team decent goaltending for the first time in years. Grateful fans swear they'll never turn on him after one cold streak. Late in the season, Burke makes a pair of great trades, getting Joffrey Lupul and Jake Gardiner from the Ducks and sending Kaberle to the Bruins for Joe Colborne and a first round pick.

The bad: The Leafs watch the Bruins use their draft pick to take Tyler Seguin. They also give a lot of money to Colby Armstrong, and any money at all to Brett Lebda.

Despite the early win streak, the team still isn't very good, finishing with 85 points and missing the playoffs yet again. That gives the Bruins another top ten pick, and ensures that nobody will ever shut up about the Kessel deal ever.

How bad was it? 65/100. It certainly wasn't a good year, but the Leafs are finally starting to look like Burke's team. Reimer, MacArthur, Grabovski, Colborne, Gardiner… you can build around that, right?

2011-12

The good: The highlight of the offseason is Burke somehow turning Lebda into a useful player in Cody Franson. Kessel scores another 30, Lupul is a point-a-game player, Grabovksi has another solid year, and Bozak is looking pretty good for a depth guy.

The Leafs start hot again, going 7-2-1. Things are going so well by December that Ron Wilson gets a contract extension for Christmas. By February 6, they're sitting at 28-19-6 and are a lock for the playoffs. The "good" section ends right about here.

The bad: The 18-wheeler goes off the cliff, as the Leafs go 1-9-1 in their next 11. Wilson is fired, and replaced by Randy Carlyle because hey, when you have a historic late-season collapse the head coach obviously has to go.

The Leafs finish with just 80 points, missing the playoffs for the seventh year in a row. Tim Connolly is yet another free agent bust, and the Leafs use their top pick on Tyler Biggs. Reimer has a so-so sophomore season after suffering a head injury suffered in October. Maybe his helmet was too hot.

Fans throw waffles. Don't ask.

How bad was it? 85/100. Leaf fans could really use a break from this team.

2012-13

The good: Leaf fans get a break from this team, and also the rest of the league, thanks to a lockout that postpones the start of the season until January. In a surprising move, Burke is fired once the lockout ends, which is a controversial move but at least sends the message that the front office will be held accountable for failure (except for the other three dozen guys in the front office, including new GM Dave Nonis, who all keep their jobs).

Before he's fired, Burke manages to fleece the Flyers into a Schenn-for-James van Riemsdyk deal, and the Leafs draft a real live prospect in Morgan Rielly. Once the season starts, Kessel's great yet again, Kadri has a breakthrough year, and Reimer stands on his head again. The team gets outshot every night, but manages to ride the percentages to a winning record and, for the first time in almost a decade, an honest-to-god playoff spot.

They take the favored Bruins all the way to a game seven, then stun the Boston crowd by jumping out to a 4-1 lead with just 12 minutes left.

The bad: Screw you.

How bad was it? 70/100. I know, I know. Everyone remembers the game seven collapse, and rightly so. But this season had its share of positives. The Leafs are back, baby!

2013-14

The good: Do we have to?

OK, fine, here goes: The Leafs acquire Jonathan Bernier in a deal that not everyone likes, but works out great. Kessel has yet another big year that includes a long extension; van Riemsdyk scores 30; and Bozak has a career year. Uh, what else… Rielly has a decent rookie year, and Mason Raymond is pretty good, I guess. Oh, and Dave Bolland plays well for a few games, which somehow turns out to be crucially important.

And despite once again being a terrible possession team that threatens the modern record for shots allowed, the Leafs are somehow still solidly in a playoff spot at the Olympic break.

The bad: Let's do this chronologically: the Leafs use a compliance buyout on Grabovski, paying him $14M to go away even though he's their best two-way center, and they let MacArthur walk as a free agent. That gives them a ton of cap space, which they use to resign Bozak and to give David Clarkson the league's worst contract. When people point out that giving seven years to a guy like Clarkson seems insane, Nonis says he doesn't care because he's only worried about year one. New MLSE CEO Tim Leiweke shows up and immediately embarrasses himself by announcing that he's planning a parade route. He also gives Nonis an extension even though he doesn't need one.

Bolland gets hurt after a month, which becomes the organization's go-to excuse for the rest of the season. Clarkson is awful. It becomes increasingly apparent that Carlyle has no idea how to fix the team's defensive problems. The team's luck runs out at the end of the season and they suddenly can't buy a win. Carlyle points the finger at Reimer, and some Leaf fans actually go along with. The whole organization starts incessantly spouting meaningless buzzwords like "compete level" and "identity".

The Leafs go 2-12-0 the close out the schedule and miss the playoffs yet again

Leweike vows that there will be culture change and hires Brendan Shanahan to make it happen. Instead, all the key decision-makers keep their jobs, and Carlyle actually gets an extension. The team is capped out, the prospect cupboard is mostly bare, and almost the entire core is locked into long-term contracts. They're screwed.

How bad was it? 93/100. What the hell have I done with the last six years of my life?

And so there you have it. It's bad. It's really bad. But no, it's not the worst it's ever been. The flaming wreckage of the JFJ/Muskoka Five era still holds the crown, although just barely. The current Maple Leafs: they really can't win anything.

(But, uh, check back after the $30 million Dave Bolland extension.)