With the NHL playoffs down to the third-round-just-get-it-over-with phase, whichever of the final four teams eventually lifts the cup, one city and one team will have an extra tough time stomaching it.

It wasn’t a great sports winter in Toronto, with the Leafs exploding all over themselves on the launch pad to open the season and the air leaking out of the balloon for the rest of the season to miss the playoffs yet again, while their roommate Toronto Raptors looked as if they would break the Toronto playoff jinx, before collapsing and possibly partying their way out of the playoffs.

And while the Leafs think about what-might-have-beens and maybe-next-years, it’s hard to say which team lifting the trophy will be the toughest for them to swallow because San Jose, Philadelphia, Montreal and Chicago will each bring a special pain to the self described center of the hockey universe.

If the Cup was to end up on the west coast in the hands of San Jose, it will be yet another expansion franchise that has been created, suffered through its losing expansion years and been built into a championship team while Toronto has embarked on, suffered through and abandoned multiple rebuilding programs.

If the Flyers are crowned as champions, it will be the third time the Leafs have watched the trophy lifted in the City of Brotherly Love since the Flyers were admitted to the league in 1967, while the Leafs exist on the fumes of their early ’90s semi-final appearances.

It doesn’t get any less painful for the Leafs looking across the Great Lakes at Chicago where the Blackhawks hold the NHL record for futility, having not lifted the cup since 1961, a title they will be more than happy to pass on to the Leafs should Chicago win it all.

And finally heading up the 401 is the team that would probably leave the Leafs with the biggest ache should they emerge as the last team standing.

Although the Leafs consider the Canadiens to be their arch rival, the teams haven’t met in the playoffs since 1979, when Montreal swept Toronto 4-0, and although the Leafs won their final cup in 1967 over Montreal, the teams have been going in opposite directions since George Armstrong fired the puck into an empty net to seal the win.

The Canadiens represent all the hopes and frustrations of the Leafs over the past 40 years, as Montreal has seen both dynasties win multiple cups and teams emerge from nowhere to win it all.

The pain gnawing on the Leafs as they watch the Canadiens this spring is especially raw, as not only were they unable to keep Montreal out of the playoffs in the last game of the season, but they have watched former Leaf defenceman Hal Gill, whom they dumped to help Pittsburgh win a Stanley Cup ring last season, now patrolling the Montreal blueline to great effect.

And while the Leafs watch teams climb the final rung of their building process or make an unexpected playoff run at glory, Toronto can dream that next year it will be their turn to give their fans something to celebrate and plan a parade for…by finally making the playoffs.