57 years of futility can be heartbreaking, especially if you’re a Toronto Maple Leafs fan. With their game seven overtime loss to the Boston Bruins in the first round of the 2023/24 playoffs the Leafs have enhanced their status as the team guaranteed to break the collective hearts of their fan base.

For head coach Sheldon Keefe Toronto’s loss to Boston marked his fifth straight playoff defeat without ever reaching the Stanley Cup finals as a head coach. This means he has now officially become a member of the Heartbreak Coaches club.

In this writer’s first book Bench Bosses: the NHL’s Coaching Elite I invented the term Heartbreak Coach to denote an NHL coach who is capable of leading his team(s) to the Stanley Cup playoffs but is incapable of securing a berth in the Stanley Cup finals. To become a Heartbreak Coach, one must earn at least five Stanley Cup playoff berths without ever reaching the Stanley Cup finals.

Sheldon Keefe has now become the 15th member of the Heartbreak Coaches club where he is tied for 13th place in the Heartbreak Coaching ranks with the late Herb Brooks and Kevin Constantine. In five tries Keefe has gotten three first round eliminations, one second round defeat and a loss in the qualifying round during the Covid-19 plagued 2019/20 playoffs.

But the heartbreaks don’t end there for Toronto.

For Maple Leafs General Manager Brad Treliving his Heartbreak Managing streak continues. Just as Sheldon Keefe is now a Heartbreak Coach, Brad Treliving has been a Heartbreak GM since the 2021/22 Stanley Cup playoffs when the Calgary Flames lost in the second round to the Edmonton Oilers (when Treliving was GM of the Flames). During his managerial tenure with the Flames Brad Treliving earned five playoff berths while suffering three first round and two second round playoff defeats.

With Toronto’s loss to Boston Brad Treliving has now moved up the NHL Heartbreak Managerial ranks. He is now tied for 12th on the Heartbreak Manager charts with Wren Blair, Gerry Meehan, and Doug Risebrough with six playoff defeats to his discredit.

What’s ironic is that Brad Treliving took over as GM of the Maple Leafs last year replacing Kyle Dubas (who is now the GM of the Pittsburgh Penguins). Dubas joined the Heartbreak Managing ranks last season when Toronto lost in the playoffs to the Florida Panthers (if you’re curious to know where Dubas ranks, Kyle is tied for 16th in the Heartbreak Managing ranks alongside Baz Bastien, George Maguire, Don Maloney, and former Columbus Blue Jackets GM Jarmo Kekalainen).

It speaks loudly about the Leaf’s propensity for futility when they replaced one Heartbreak GM in Kyle Dubas for an even worse Heartbreak GM in Brad Treliving.

But Heartbreak Coaching and Heartbreak Managing do not belong exclusively to the Toronto Maple Leafs.

Other franchises suffer from it too.

Take the Carolina Hurricanes, although still alive in the playoffs they have a Heartbreak Coach in Rod Brind’Amour (six playoff defeats with no Stanley Cup finals berths as a head coach) and a Heartbreak Manager in Don Waddell (seven playoff defeats with no Stanley Cup finals berths as a GM).

Time will tell if they add to their mutual playoff losing streaks.

There is also Winnipeg Jets GM Kevin Cheveldavoff. He (like Don Waddell) has seven playoff defeats without ever earning a ticket to the Stanley Cup finals as a GM.

Time will also tell if he adds to his skein of playoff futility.

There are potential future candidates for the Heartbreak Coaching and Heartbreak Managing ranks.

Please keep your eyes on Minnesota Wild head coach John Hynes. He has earned four playoff berths without ever winning a ticket to the Stanley Cup finals as a head coach.

Please also watch Los Angeles Kings GM Rob Blake and Minnesota Wild GM Bill Guerin. The two had both suffered four playoff losses as NHL GMs without ever reaching the Stanley Cup finals.