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?

With the Leafs mired in another death spiral, the core is coming under increased scrutiny. The major question in Toronto is whether you can win with Phil Kessel and Dion Phaneuf.

It's certainly possible. And you have to look no further than the team who has won two of the last five Stanley Cups.

"Does it hurt to watch Tyler Seguin?"

That's a common question many Leafs fans get, especially as Seguin launches an offensive assault on the league.

You may have heard this before, but the Maple Leafs traded the draft pick that eventually became Seguin. The Phil Kessel trade is rarely discussed so don't feel bad if you didn't know this fact. Oh, what's that? You've heard that before. Of course, because by law the Kessel-Seguin swap needs to be brought up EVERY SINGLE DAY. For eternity.

But unlike other painful trades of the past that continually hurt Leafs Nation's collective psyche (like the Tom Kurvers-pick-that-became-Scott Niedermayer deal that everyone was reminded of as Cody Franson crept up on a Kurvers points streak record), the Seguin trade doesn't hurt. And I'm not just saying that because the Leafs have killed off any feelings I still might have inside of me.

One of the most debated Leafs signings in recent years, Tyler Bozak is nearly on a point-per-game pace in year one of a five-year deal and could surpass his career high in points in considerably fewer games.

But has he really improved?

MURICA!!!

National pride was on the line for Canada in Vancouver four years ago and a similar pressure exists in Sochi for the Russians. The added element to this year's Olympics should make for another memorable hockey tournament.

But there is more to these games than just Russian national pride and/or Canadian interloper heartbreaking. There are plenty of players with things to prove or compelling storylines of their own.

Here are some of the interesting players to follow during this year's Olympics.

The Leafs train keeps rolling, wobbling only momentarily during the first month of the season. It doesn't matter how many shots the Leafs allow, Jonathan Bernier and James Reimer are there to stop them all, and the forwards are scoring more than an bearded high schooler driving a Firebird.

Hours before the start of the regular season, Phil Kessel re-signed with the Toronto Maple Leafs for $64 million over 8 years.

With a number that big there are sure to be people losing their minds. To help you understand I put together a handy guide to answer any concerns you might have about the richest deal in Maple Leafs history.

The Leafs made the playoffs for the first time in nine years and I almost missed it.

With how the series came crashing down catastrophically at the end, maybe that would have been for the best. But even after enduring insanely improbable heartbreak, the Leafs at least had a chance. And after nearly a decade lost in the bleak wilderness of apathy, I wouldn't trade this season, ending and all, for another lottery finish.

I almost missed the most relevant Leafs hockey in nine years because I was invited to a destination wedding in Punta Cana that inconveniently coincided with games 3-6.

Tip for anyone thinking about getting married: Book it before or after the playoffs, even if you're an Oilers fan and the chances of your wedding interfering with the playoffs is nil (Hey! I can make fun of other teams that don't make the playoffs now and it feels great). Otherwise, make accommodations for your insane hockey friends. For example, I went to a Stag and Doe on the night of Game 2 and one of the groomsmen brought his satellite dish from home and hooked it up so no one had to miss the game (or, more likely, the Stag and Doe). If you're having your wedding this might interfere with things like speeches, but just crank up the volume during intermission and it'll be like Don Cherry is giving you a personal wedding toast. "Keep your stick on the ice, even in the bedroom."

Bringing a satellite dish to Punta Cana probably wasn't going to happen, not that I was worried when I was first invited. I've had my plane tickets booked since last Autumn, well before the NHL lockout even ended, so I initially didn't think my trip south would be anything other than blissful. I wasn't overly optimistic about Toronto's chances heading into the season either, so even when the lockout ended I didn't think a trip in early May would be an issue. There are 10-year-old children who didn't even know the Leafs were allowed to play hockey in May. But as the season crept along, and the Leafs continued to pile on wins, I began to slowly realize that this trip was going to prove challenging.

For normal people, taking a trip to an all-inclusive resort with beautiful sunny weather would wash away any thoughts about a hockey game. Unfortunately, as a Leafs fan, I'm far from normal, and I was in a slight panic. Where was I going to watch the game? Was there an ESPN5 that would at least show some highlights, albeit after three hours of football and basketball coverage? How could I argue with bartenders about the merits of Jake Gardiner over Mike Kostka if I couldn't speak a lick of Spanish (other than "dos cervezas por favor").

After a win in Game 2, it became even more imperative that I watch this series. It was actually going to be a series, not a one-sided beating like many predicted. Luckily, there was a good contingent of Leafs fans going to the wedding, so I wouldn't be alone on my quest to find hockey.

And a quest it was. Here is how my (possibly hazy) memory recalls the week.

Looking at the Leafs' stats after the season is a little strange as the lockout caused far lower totals than I'm accustomed to seeing. I'm used to thinking that 30 goals is a pretty solid season for a sniper and it's hard to quickly determine what that 30-goal mark would be during a 48-game season. So to get a better understanding of what type of season the individual Leafs players just had I prorated their 48-game totals to their corresponding 82-game numbers.

The one major caveat of this table is that the missing 34 games of the season would not necessarily play out exactly the same as the other 48, so simply prorating players' 48-game stats over 82 games isn't exactly a precise measure of what an 82-game season would look like. For example, Joffrey Lupul, a career 11.55% shooter, was probably not going to continue shooting 26% over a full year.

Regardless, this table is a quick and dirty look at what the Leafs might have produced in the alternate universe where Gary Bettman didn't flush away the first 34 games of the season.

	Lockout-Shortened 2013 Season				Stats Over Full Season
	GP	G	A	Pts	GP	G	A	Pts
Phil Kessel	48	20	32	52	82	34	55	89
Nazem Kadri	48	18	26	44	82	31	44	75
James van Riemsdyk	48	18	14	32	82	31	24	55
Cody Franson	45	4	25	29	77	7	43	50
Dion Phaneuf	48	9	19	28	82	15	32	48
Tyler Bozak	46	12	16	28	79	21	27	48
Nikolai Kulemin	48	7	16	23	82	12	27	39
Clarke MacArthur	40	8	12	20	68	14	21	34
Joffrey Lupul	16	11	7	18	27	19	12	31
Jay McClement	48	8	9	17	82	14	15	29
Mikhail Grabovski	48	9	7	16	82	15	12	27
Carl Gunnarrson	37	1	14	15	63	2	24	26
Matt Frattin	25	7	6	13	43	12	10	22
John-Michael Liles	32	2	9	11	55	3	15	19
Leo Komorov	42	4	5	9	72	7	9	15
Mark Fraser	45	0	8	8	77	0	14	14
Mike Kostka	35	0	8	8	60	0	14	14
Ryan O'Byrne	42	2	4	6	72	3	7	10
Frazer McClaren	36	3	2	5	62	5	3	9
Colton Orr	44	1	3	4	75	2	5	7
Jake Gardiner	12	0	4	4	21	0	7	7
Korbinian Holzer	22	2	1	3	38	3	2	5
Ryan Hamilton	10	0	2	2	17	0	3	3
Joe Colborne	5	0	0	0	9	0	0	0
Mike Komisarek	4	0	0	0	7	0	0	0