The Maple Leafs kicked off their rebuild by trading star winger Phil Kessel to the Pittsburgh Penguins for a package of prospects and picks, finally ending the contentious Phil Kessel era in Toronto.

In exchange for Kessel, who goes to Pittsburgh along with Tyler Biggs, Tim Erixon, and a 2016 2nd round pick, the Leafs received Kasperi Kapanen (2014 1st round pick), Scott Harrington (2011 2nd round pick), veteran Nick Spaling, and a 2016 1st round pick and 3rd round pick. The Leafs also agreed to pick up 15% of Kessel's salary, totalling $1.2 million a season.

One of the biggest decisions the Maple Leafs must make this off-season is deciding what to do with Phil Kessel.

Although Kessel is a dynamic offensive player, the Leafs have failed to surround him with talent and the team has wasted Kessel's prime years. There are still good years left for Kessel, but with the Leafs embarking on a full-scale rebuild it's likely those years will go to waste in Toronto. And by the time the Leafs start to rise from the bottom of the league, Kessel will be hitting the decline phase of his career. The wisest decision, therefore, would be to deal him this summer.

But what type of return can the Leafs get for Kessel. Luckily for us, a superstar winger with a massive contract was traded within the past few years and can give us a good idea of what Kessel might fetch in a trade. I'm referring, of course, to Rick Nash.

With the Leafs set to embark on a full-scale rebuild, the most pressing question among Toronto fans is simple: How long until the Leafs can contend.

Re-building is not for the faint of heart. It takes plenty of years of being utterly terrible before the first signs of tangible progress, and sometimes plenty more after that before reaching the ultimate prize (just ask the St. Louis Blues).

To get a better understanding of just how long a rebuild might take in Toronto I looked at three of the past four Stanley Cup winners to see how they did it. I excluded the Boston Bruins because they didn't really rebuild, they succeeded in pulling off the magical re-tool on the fly, in large part because they made the greatest free agent singing ever (Zdeno Chara) and lucked into two franchise goalies (in one case the luck was having a team as stupid as the Leafs to trade with). Basically, the Bruins model is not easily replicable.

For the Kings, Blackhawks, and Penguins, I defined the start of the rebuild as the first season in which they flamed out after having been in the playoffs or at least in playoff contention for a number of years. If you're in the playoffs or at least close enough to have a shot late in the season (as the Kings were from 2003-2005) you aren't rebuilding. It's not until a team drops dramatically in the standings that they typically commit to a full rebuild.

So how did they do it?

On the one-year anniversary of his hiring as Toronto Maple Leafs general manager, Dave Nonis is witnessing his team implode. Toronto has only two regulation wins in their last 23 games and only four in the 30 games since a 10-4 October.

After making the playoffs last season the Leafs have taken a gigantic step backwards in 2013-14, although they are miraculously still in a playoff spot thanks to a terrible Eastern Conference.

Now seems like a good time to evaluate Nonis' first year on the job.

On the day of the Winter Classic the Leafs made a trade, consummating the oft-talked about John-Michael Liles for Tim Gleason swap with the Carolina Hurricanes.

The deal is a lateral move, both teams dealing overpriced defenders with two additional years on their contracts, but one in which the two players might provide better results with a change of scenery.

After one game of Jay McClement as the team's best natural centre, the Leafs addressed their desperate need down the middle by making a deal with the Anaheim Ducks.

The Leafs acquired Peter Holland and Brad Staubitz from the Ducks on Saturday, shipping out Jesse Blacker, a conditional third-round pick (that could become a second-round pick if he plays 25 games), and a seventh-round pick (which was originally Anaheim's).

The primary parts of the deal, Holland and Blacker, were both blocked in their respective organizations, with Anaheim deep at centre and Toronto deep on the blueline. Blacker had fallen so far on the depth chart in Toronto that he has been a healthy scratch for much of the year with the Marlies.

Dave Nonis did well to deal from a position of strength to get a quality NHL-ready prospect when the Leafs were in such dire need for help.

The Maple Leafs traded Joe Colborne for a song because the organization values face punching over skill.

Late Saturday night the Maple Leafs dealt Joe Colborne to the Calgary Flames, a team even more desperate for centres, for a conditional fourth-round draft pick. The pick could turn into a third-round pick "if certain conditions are met in the upcoming season".

The Trade that shocked the hockey world happened 25 years ago, ripping Wayne Gretzky from Edmonton and forever making Peter Pocklington a pariah in the City of Champions. But there exists an alternate universe where Wayne Gretzky was never traded from Edmonton—because he was a Winnipeg Jet.

In Peter Gzowski's best-selling classic The Game of Our Lives, which follows the 1980-81 Edmonton Oilers, a team on the brink of becoming a dynasty, Gzowski tells a story of how Wayne Gretzky was almost traded to the Winnipeg Jets instead of the Edmonton Oilers. The deal never happened because Jets owner Michael Gobuty wasn't a bolder backgammon player.

Heading into the final year of his contract, Kris Letang might be pricing himself out of Pittsburgh.

The Penguins are working on extending Letang, but are hesitant to offer much more than $6 million a season. Pierre LeBrun doesn't think Letang will sign for any less than $7 million a season.

The Penguins have the cap space to offer Letang a contract worth $7 million a season, but thanks to massive contract extensions for Sidney Crosby and Evgeni Malkin, more than $34 million is already committed to six players in 2014-15, and adding Letang's big ticket would put them in a cap squeeze.

The Penguins are also concerned about whether Letang is worth elite defenceman money. According to Rob Rossi, "Letang is not the consensus best defenseman on the Penguins, at least in the eyes of management and coaches."

And with the bevy of young defence prospects in the Penguins' system, Rossi believes Letang has become a "must-move player" for GM Ray Shero. The Penguins could decide to keep Letang next season and go for a cup, return be damned, but a trade seems likelier, with CBC's Elliotte Friedman reporting teams are preparing offers in case the two sides fail to reach an agreement.

If the Penguins do decide to trade Letang, there will be plenty of suitors, despite the high cost to acquire the Norris Trophy finalist. More concerning, however, is Letang's desire to be paid like an elite defencemen. Sure, he's scored 190 points over the last five years, tied for 11th among defencemen, but are there enough holes in his defensive game to cause teams to look elsewhere for defensive help?

Is Letang worth $7 million or more over 5-8 years, or is this a case of buyer beware?

A lockout hasn't stopped the endless Roberto Luongo rumours.

Last week, Sportsnet's John Shannon reported that there is an agreement between Toronto and Vancouver that would send the 33-year-old netminder to the Leafs once the lockout ends. Apparently Brian Burke and Mike Gillis (who both denied Shannon's report) have been in communication for a long time, ever since the Canucks reportedly asked for Tyler Bozak, Jake Gardiner, Matt Frattin, and a first-round pick at June's entry draft. That asking price was obviously a non-starter for the Leafs, but a deal surrounding Bozak is supposedly very much alive.

However, with the owners' latest CBA proposal, which would stick teams who sign a player for more than five years with that player's cap hit upon retirement, there is speculation in some corners that the price just went up.

Not so long ago, Tomas Kaberle was the only bright light during increasingly dark times in Toronto.

With the Leafs attempting to rebuild, Kaberle's name was linked in just about every trade rumour imaginable. Finally, after what seemed like years of endless rumours, Kaberle was dealt to the Boston Bruins for Joe Colborne, a first-round pick, and a conditional second-round pick, which eventually went to Toronto after Boston won the 2011 Stanley Cup.

However, Kaberle has been involved in trade talks long before Brian Burke struggled to bring respectability back to Toronto. Here are five major trades that would have seen Tomas Kaberle packing his bags and the history of the Toronto Maple Leafs change dramatically.

The San Jose Sharks are at a crossroads.

After making back-to-back Western Conference Finals in 2010 and 2011, the Sharks were ousted in the first round this season by the St. Louis Blues, a younger, faster, and hungrier squad. The Sharks squeaked out a 3-2 win in double overtime in Game 1, but lost the next four straight. Overnight, it looked like San Jose’s window to contend slammed shut.

That’s why more than any other team, the Sharks need to trade for Rick Nash.

A stray elbow to the head turned more than James Reimer’s world upside-down last season; it sent Brian Burke’s carefully constructed plan for contending crashing to the ground. Now Burke must search desperately to find a veteran netminder capable of leading the Maple Leafs to the playoffs.

Although Ben Scrivens just finished an amazing season in the AHL, winning goaltender of the year, the disaster of 2011-12 means the Leafs cannot start training camp pinning their hopes on two unproven goalies. With public anger rising around Burke, entrusting the keys to the post-season to Reimer and Scrivens won’t happen. Burke was burned by this same gamble last season and is in no position to roll the dice again.

More importantly, failing to find a goalie was the same problem that eventually caused his firing in Vancouver. If he doesn't find a proven goalie to share the net with either Reimer or Scrivens it could ultimately be his downfall in Toronto as well.

According to Albert Einstein, insanity is doing the same thing over and over again and expecting different results. If one of history's greatest scientists was alive today he might look at the Calgary Flames and see insanity personified.

The Calgary Flames have missed the playoffs for the past three seasons and haven't passed the first round since making the Stanley Cup Final in 2004. The roster is aging and the prospect pool is thin, which seem like good reasons to start a rebuild, but Calgary has other ideas. The Flames are blind to the apparent, and yesterday's hiring of Bob Hartley confirms that, although not on the surface.

In 1991, the Quebec Nordiques had the privilege of drafting first overall for the third straight year, giving them the chance to draft Eric Lindros, dubbed the next Wayne Gretzky. Lindros, however, had other plans, refusing to play in Quebec and holding out until being traded to Philadelphia the next season. Flash-forward 20 years and the Edmonton Oilers own the first overall pick for the third consecutive year. Like the Nordiques before them, they too might see that pick slip away, albeit for entirely different reasons.

The Oilers are in a unique predicament this year: they have spent the last few years drafting high-end forwards and lack the same quality of talent on the backend. Although Edmonton’s system does possess a good amount of NHL-calibre defenemen, there is not a No. 1 quality blueliner among them. The Oilers have a choice: continue to add up front, which is almost entirely unnecessary, or deal the pick to add much-needed pieces to the blueline.

Although this draft class is full of defencemen, the first few picks will likely be forwards. This means that the Oilers can trade down, possibly as low as five, and still have a chance to take the best defenceman in the draft.

By trading down the Oilers would also be able to grab a young player and/or a handful of picks from a team eager to land Nail Yakupov, the highly skilled Russian winger from the OHL. This is an opportunity for the team to fill their greatest need, and at the same time add more pieces to their growing cupboard.

It isn’t every year that a team is willing to trade away the first overall pick, and the return varies based on the needs of the teams involved. But we can look back at some of the teams that have traded the No. 1 pick to see what type of return the Oilers can expect and whether it is in their best interest to pass on Yakupov.

Rick Nash is on the block. After a dismal season in Columbus it appears as if the franchise winger is available at the right price, for the right team.

Did you hear that? RICK NASH! First overall pick. Olympian. Maurice Richard winner. Prisoner of Columbus. That Rick Nash.

On Monday, RDS reported Nash was on the market, and on Tuesday the Columbus Dispatch confirmed that the Blue Jackets were willing to listen to offers for the face of the franchise.

In less than a week Nash went from untouchable to available. Things change quickly in the NHL.

It's amazing that Columbus would let GM Scott Howson deal the most important player in the history of the Blue Jackets, but you don't have a perennial cellar dweller by doing things the right way. Regardless, Nash is a premier talent and teams will be lining up for his services.

However, Nash has a no-movement clause, and TSN reports that he has likely given a very small list of teams that he would willingly play for. That means even if every team in the league sent a trade proposal to Howson, he immediately must disregard almost all of them, or at the very least give a quick glance and cry over potential missed opportunities.

From now until the deadline, all you're going to read or hear about is Rick Nash. The prevailing thought is that any team would be crazy not to go all in on Nash. Unfortunately, it's not quite so simple. Nash would be a great fit for some teams, but not others. I'm not convinced the Maple Leafs are the former.

To figure it all out I debated myself in a segment I like to call "Point/Counterpoint".

Making a trade is always a risky proposition. You may think you know what you're giving up, but sometimes, especially with young players, you really have no idea. If you have to give something to get something, in a lot of cases that something you give could turn out to be a lot more than you expected.

It’s very rare that you can rummage in the dumpster out back, throw your findings in an old, dirty burlap sack and get Dion Phaneuf. It just doesn’t happen all that often, especially now that Darryl Sutter isn’t employed as a GM.

Sometimes you're the one giving up the Dion Phaneuf in the deal. In other words: the loser.

Being on the losing end of a deal is a bad feeling. There’s the shame in knowing that your team once had that certain player now dominating the league, and there’s an even greater shame in knowing the team you support is run by people dumb enough to let that player get away.

That’s the feeling Toronto fans get when they think about Tuukka Rask, Boston’s backup goalie who just needs to wait for Tim Thomas to vacate the crease before becoming the league’s best netminder. He's already amazing, but Thomas is so unhumanly good that Rask sits patiently and bides his time before everyone can see his awesomeness 60+ times a year. Thanks, JFJ!

It’s also the feeling Leafs Nation gets whenever Tyler Seguin’s name shows up in the boxscore. Although this feeling is somewhat mitigated every time Phil Kessel’s name shows up, which, thankfully, is quite often.

In addition to Seguin and Rask, another former Leaf is doing quite well for himself. Kris Vertseeg has 28 points in 26 games for the Florida Panthers. He sits 10th in points and is in the top-20 in goals.

But despite how well Versteeg is playing right now, very few Maple Leafs fans are bemoaning his loss. There are a few reasons for this.

When I heard Kyle Turris wanted to be traded from Phoenix my first thought was: "just wait a few months and the team will move itself". But I guess that wouldn't solve Turris' problem of playing for Dave Tippet, in what he presumably considers a bad situation for himself.

I also began to wonder whether or not Turris was actually a bust. He was drafted third behind Patrick Kane and James van Riemsdyk in 2007 and he still hasn't really cracked the NHL (last year he played in 65 games). Turris feels like a bust because Kane has seemingly been around for forever, so what's taking Turris so long?

Then I looked at his age and realized he was 22. For comparison's sake, Nazem Kadri is 21. If I was going to label Turris a bust, then I better start preparing to do the same for Naz. I wasn't prepared to do that, I still view Kadri as a quality prospect (hold on while I adjust my rosy Leafs-coloured glasses).

With super rookies like Sidney Crosby, Alex Ovechkin, and to a lesser extent, players like Jeff Skinner and Ryan Nugent-Hopkins, coming into the NHL and making an immediate impact at 18, it becomes easy to write off someone like Turris for failing to make a similar impact 3-4 years later. But the truth is that it is very rare for an 18-year-old to play at a high level. Most often, players take years to develop into quality NHLers.

So altering my thinking through that lens, it became clear why some teams would still have an interest in Kyle Turris, and why the Phoenix Coyotes didn't give into his trade demands. You don't just give away a player you took with a lottery pick, even if it's three-and-a-half years later.

For today's Good Point article I wrote about the whole Turris saga.

There's a problem with Alexander Ovechkin. It doesn't matter that he has the 7th highest points-per-game of all-time, or that he's cracked 50 goals and 100 points four times. It doesn't matter that he's won two Hart Trophies. There's a problem.

Honestly, I have been really proud of this MSpaint-job I did sometime last year and I've had no idea when I could actually write a Cliff Fletcher post to use it on. To solve that problem I thought it was about time we start appreciating the wonder that was Cliff Fletcher's second time around in Toronto. He did sign Jeff Finger, which is always good for a few laughs, but that's no reason to consider his Toronto redux anything other than a complete success.