Chicago and Pittsburgh both took advantage of its previous plight by utilizing high draft choices to build the core of its franchises.
For Leaf fans with insufferable angst, these are the horror stories that bring into question the merit of the Kessel trade - although Kessel was a top-five draftee himself, so it could be argued the trade was one first-round pick and a second.
Unfortunately for the 'Hawks, they have fallen victim to cap-era economics and were unable to retain nine players who contributed to last year's Cup run.
While you can't argue with the results of its all-in move, Chicago is suffering this season without the depth that made it the best team in hockey.
The Penguins are also cash strapped, with 44-percent of their cap tied up in Sidney Crosby, Evgeni Malkin, Marc-Andre Fleury and Jordan Staal.
But with a foundation that includes two first-overall and two second-overall selections locked up long term, any GM would be willing to take on Pittsburgh's problems, or lack thereof.
It's not entirely fair to make comparisons to the Detroit Red Wings - they are, unequivocally, in a league of their own.
Unlike the Penguins or Blackhawks, the Wings relied on good scouting and player development to build the most unconventional powerhouse in hockey.
The only first-round pick on their 2008 Cup-drive roster was Niklas Kronwall. Pavel Datsyuk and Henrik Zetterberg didn't emerge as superstars until they were 27 and 26 respectively, while playoff hero Johan Franzen didn't make a significant impact until he was 28.
Although Detroit had the luxury of allowing its recent superstars to grow on the farm or develop overseas, the efficiency in which it has been able to find gems in the later rounds of the draft is mind-boggling.
Even Nicklas Lidstrom, the best defenseman of this generation, was a third- round pick who came into the league and dominated as a 21-year-old.
It's hard to fathom any team replicating the Wings' savvy ways, but it goes to show that there is more than one round in the draft for a reason.
Anaheim and Carolina took the middle road, utilizing a couple of draft picks and piling on the meat and potatoes through trade and free agency.
If Leaf Nation is looking for a model to call its own, it's the Ducks.
Former GM Bryan Murray was responsible for selecting first-rounders Corey Perry and Ryan Getzlaf, who were important players but not the leaders during Anaheim's championship season.
Murray's predecessor, Pierre Gauthier, brought in goaltender J.S. Giguere, the undrafted Andy McDonald and Selke finalist Samuel Pahlsson.
For his part, Brian Burke brought in free-agent stars Teemu Selanne, Chris Pronger and Scott Niedermayer - the final pieces to put the team over the top.
Carolina, while not as active in the free-agent market, took a similar approach.
Eric Staal (2nd overall in 2003) was a man possessed in 2005-06, racking up 128 points between the regular season and playoffs as a sophomore.
But besides Staal's contributions and the out-of-the-blue performances by Cam Ward and Justin Williams, the Hurricanes got by with rugged hockey and veteran leadership provided by Rod Brind'Amour, Ray Whitney and Cory Stillman, among others.
The Leafs have a long way to go before they are playoff contenders, let alone Stanley Cup champs.
But simply because Toronto is without its first-round draft pick yet again doesn't mean all is lost.
Just ask the Florida Panthers, Columbus Blue Jackets and Atlanta Thrashers who seem to be stuck in a perpetual rebuild.
Toronto has two good prospects in Luke Schenn and Nazem Kadri, and has made significant moves to improve the team through trades.
The only roadblock will be tying up impact free agents, a tough task in today's NHL where teams are locking up their star players before they hit the open market.
But the road to the Stanley Cup is long and weary, with plenty of twists and turns and off-road paths - the straight line on cruise control doesn't always get you there first.