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?

Los Angeles Kings
Rebuild starts: 2006-07
First playoff appearance: 2009-10
Stanley Cup: 2012-13

Notable draft picks during rebuild stage
2007: Wayne Simmonds (2nd round, 61st overall), Alec Martinez (4th round, 95th overall)
2008: Drew Doughty (1st round, 2nd overall), Slava Voynov (2nd round, 32nd overall)
2009: Brayden Schenn (1st round, 5th overall)
Whiffs: Thomas Hickey (1st round, 4th overall, 2007), Colten Teubert (1st round, 13th overall)

Notable acquisitions during rebuild stage
2007: none
2008: Matt Greene, Jarret Stoll,
2009: Justin Williams, Ryan Smyth

Notable signings during rebuild stage
2007: Michal Handzus, Kyle Calder, Brad Stuart, Ladislav Nagy
2008: none
2009: Rob Scuderi, Jake Muzzin

Additional draft picks acquired: a net of two additional 1st round picks and three additional 2nd round picks between 2006-2009

The Kings' rebuild started with a solid foundation, as the team was able to find stars in Anze Kopitar, Dustin Brown, and Jonathan Quick outside of the top-10 draft picks in the years when they were still in playoff contention. Having already secured these players was integral as the Kings ultimately missed on two first round picks during their rebuilding stage — Thomas Hickey being an especially bad pick as LA owned the fourth overall pick that draft and reached for Hickey who Central Scouting ranked as the 17th best prospect.

Having Kopitar and Quick meant the Kings already had a No. 1 centre and a No. 1 goalie so they only really needed to find a No. 1 defenceman during their rebuild before having a solid enough foundation for true contention. Then drafting Drew Doughty and having him be able to make an almost immediate impact in the NHL is the main reason the Kings' rebuild took only three seasons before they were back in the playoffs. As you will see with the Hawks and Penguins not all rebuilds are that quick.

Chicago Blackhawks
Rebuild starts: 2003-04
First playoff appearance: 2008-09
Stanley Cup: 2009-10

Notable draft picks during rebuild stage
2004: Dave Bolland (2nd round, 32nd overall), Bryan Bickell (2nd round, 41st overall), Troy Brouwer (7th round, 214th overall)
2005: Nicklas Hjalmarsson (4th round, 108th overall)
2006: Jonathan Toews (1st round, 3rd overall)
2007: Patrick Kane (1st round, 1st overall)
2008: none
Whiffs: Cam Barker (1st round, 3rd overall, 2004), Jack Skille (1st round, 7th overall, 2005), Kyle Beach (1st round, 11th overall, 2008)

Notable acquisitions during rebuild stage
2004: Lockout
2005: Patrick Sharp, Radim Vrbata
2006: Martin Havlat, Michal Handzus
2007: Kris Versteeg
2008: Andrew Ladd

Notable signings during rebuild stage
2004: Lockout
2005: Nikolai Khabibulin, Adrian Aucoin
2006: none
2007: none
2008: Brian Campbell, Cristobal Huet, Antti Niemi

High draft picks acquired: a net of six additional 2nd round picks from 2003-2008

The Blackhawks too had a solid foundation to start as they were able to select Duncan Keith, Brent Seabrook, and Dustin Byfuglien during the years they were a playoff team, and only Seabrook was taken in the first round.

As much as people attribute Chicago's success to drafting Jonathan Toews and Patrick Kane in successive years with high draft picks, their continued dominance is also in large part thanks to their excellent drafting outside the first round. Their ability to still make quality picks later in the draft is a major reason why picking Jack Skille (7th overall) and Cam Barker (3rd overall) didn't kill them.

Chicago also did a pretty good job on the trade market, netting guys like Patrick Sharp, Andrew Ladd, and Kris Versteeg for cheap. Their major downfall was trying to accelerate their rebuild through the free agent market — disastrously in 2005, and somewhat less so in 2008 (because they still won a cup), although those decisions still gutted the post-championship Hawks and forced them to re-tool on the fly.

Pittsburgh Penguins
Rebuild starts: 2001-02
First playoff appearance: 2006-07
Stanley Cup: 2008-09

Notable draft picks during rebuild stage
2002: Ryan Whitney (1st round, 5th overall), Max Talbot (8th round, 234th overall)
2003: Marc-Andre Fleury (1st round, 1st overall), Matt Moulson (9th round, 263rd overall)
2004: Evgeni Malkin (1st round, 2nd overall), Alex Goligoski (2nd round, 61st overall), Tyler Kennedy (4th round, 99th overall)
2005: Sidney Crosby (1st round, 1st overall), Kris Letang (3rd round, 62nd overall)
2006: Jordan Staal (1st round, 2nd overall)
Whiffs: none (you can make a strong argument for Whitney but they parlayed him into Chris Kunitz)

Notable acquisitions during rebuild stage
2002: none
2003: none
2004: none
2005: none
2006: none

Notable signings during rebuild stage
2002: none
2003: none
2004: Lockout
2005: Sergei Gonchar, Ziggy Palffy, John LeClair
2006: Jarkko Ruutu, Mark Recchi

High draft picks acquired: a net of one additional 2nd round pick from 2001-2006

It's hard to look at the Penguins and see anything other than a pure tank in progress. The Penguins didn't make one notable acquisition or signing for three seasons (although to be fair one of those was a lockout) and didn't really try to improve in any way until they selected Sidney Crosby. But they also did a terrible job of selling off players for assets as they only managed to net one additional second round pick during their rebuild period and completely bungled the returns for both Jaromir Jagr and Alex Kovalev.

Unlike the Kings and Hawks, the Penguins didn't really miss on any of their high picks, which is one of the reasons why it didn't hurt them that their only real important carry over from their playoff years was Brooks Orpik. It also helped that they were able to find a top-pairing defenceman (Kris Letang) outside of the first round.

Ultimately, the Penguins rebuild was one that was hard to screw up as they lucked into a few years where the top talent was generational—Crosby and Malkin—unlike in other years where it's merely good to great (#OilersProblems). It's a good thing they were so lucky too, because they really didn't do anything to help themselves.

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What do these three case studies mean for the Maple Leafs?

At a minimum, the Leafs are looking at three seasons outside the playoffs, most of which will be pretty terrible. Although after almost a decade of that type of play already, doing so with a clear purpose sounds pretty good. Going by the same methodology as I used with the above teams, that would put the Leafs rebuild starting last season in 2013-14, meaning at the earliest the Leafs can hope for a playoff berth is in 2016-17, which sounds hopelessly optimistic (especially considering it's only now the Leafs realize they need to rebuild). If the Leafs take a track more similar to the Penguins or Blackhawks you're looking at a playoff berth in 2018-19, meaning the next three seasons will be rough. That sounds about right, and still plenty optimistic.

Toronto Maple Leafs
Rebuild starts: 2013-14
First playoff appearance: 2018-19?
Stanley Cup: 2020-21?

As for what lessons the Maple Leafs can learn, one of the most important seems to be amass picks. Both the Hawks and Kings acquired a bunch of additional picks in the first two rounds and it's no surprise that they were two of the better teams at finding talent outside the first round. The chances of finding not only an impact player, but even a guy who hits 50 career NHL games drops dramatically as the draft progresses, so having extra chances at unearthing a gem is extremely helpful. More picks can also lessen the impact of whiffing on any one, as there are more chances to recover.

Second, stay away from big free agent deals, at least until the team is on the cusp. Both the Hawks and Kings made some regrettable deals early on in their rebuilds and had to work so much harder in other areas to overcome them. The Leafs should focus on cheap, short-term deals like they did last summer and try to flip those guys at the deadline for picks or prospects to continually stockpile the system.

Additionally, unless you're at the top of the draft and have a generational talent waiting (can the Leafs finish bad enough for either Connor McDavid or Jack Eichel?) having a young, strong foundation is a major factor in ending the perpetual rebuild cycle.

Can Morgan Rielly become the Leafs' Duncan Keith? Will Stuart Percy or Connor Brown make an NHL impact? What about Jonathan Bernier, Nazem Kadri, Jake Gardiner and James van Riemsdyk? By the time the Leafs can contend those four will be in their late 20s, but the Hawks won their first Stanley Cup with key pieces like Patrick Sharp (28), Marian Hossa (31), and Brian Campebell (30), so they can still help the Leafs in the future.

It's also important to remember that the three teams above represent the absolute best case scenario. There are plenty of teams that have gone through similar rebuilds and found absolutely zero success (again, #OilersProblems). Even when teams do manage to make it out of the rebuilding stage there is still no guarantee they will have any real playoff success (like both the Blues and the Capitals).

The first step, however, is getting out of the rebuild stage and building a contender. And what it will come down to is drafting. Even if Rielly and Bernier are legitimate No. 1s at their position in the future, the Leafs still need to get an elite centre (almost always filled with a top draft pick) and quality pieces throughout the lineup. The Leafs hired Mark Hunter to lead their scouting and player evaluation department and over the next few seasons he's going to have to earn his pay cheque. Otherwise it will be another long walk in the wilderness for Leafs fans.