Now Edmonton and Toronto are both sitting in a wild-card spot, battling down the stretch for a playoff berth.
There are striking similarities behind their rebuilds. In the spring/summer of 2015, both teams hired Stanley Cup-winning general managers, then selected highly skilled forwards at the top of the draft. Each club then showed progress in 2015-16, but ultimately finished last in their conference. This season, they are mirror images, separated by just one regulation win (Toronto has 30, Edmonton 31).
With young superstars in place, they are traveling the path of teams like the Chicago Blackhawks and Pittsburgh Penguins, who were once punchlines, then turned high draft picks into a decade of success.
It's very likely they will be legitimate contenders for years to come, but are either the Oilers or Leafs good enough to win the Cup this year?