The Toronto Maple Leafs have the NHL’s longest active playoff streak at nine seasons. They also have the longest string of postseason misery, which dates back to their most recent Stanley Cup championship in 1967 and has been particularly painful the past few seasons.

The latest disappointment was a 6-1 loss Sunday to the Florida Panthers in Game 7 of the second round. The Leafs dropped their final two home games by a combined score of 12-2 and were booed off the ice after blowing a 2-0 series lead.

Toronto has failed to advance past the second round under three different coaches (Mike Babcock, Sheldon Keefe and Craig Berube) and three general managers (Lou Lamoriello, Kyle Dubas and Brad Treliving).

The one constant since 2018-19 has been a “Big Four” of elite forwards Auston Matthews, Mitch Marner, John Tavares and William Nylander. They have two playoff series wins to show for it. It could go down as the biggest waste of talent in league history.

It could be time to break up the band. Could the Detroit Red Wings capitalize?

Detroit is dealing with a different kind of misery – a nine-year playoff drought. The pressure is on general manager Steve Yzerman to make a bold move entering his seventh season.

Marner appears destined to leave Toronto and become the biggest name in the free-agent market on July 1. If so, Yzerman is certain to make a pitch.

Marner is coming off a contract with an average annual value of $10.9 million and might cost upwards of $12 million per season on a maximum seven-year deal (teams can sign their own free agents for eight years). The Red Wings previously might have been reluctant to pay anyone more than Dylan Larkin, whose AAV is $8.7 million, but not anymore. Yzerman said as much during his postseason media address.

“We’re going to look at any good player, any player that can help us in any role,” Yzerman said three weeks ago. “If there’s a player worthy of spending whatever amount on that has an interest in playing in Detroit and fits a need for us, absolutely, we would try to do that. We’re in a different stage than we were maybe five years ago in that we have a good, young nucleus of players and if we can add to that with a prominent free agent, we’d certainly entertain that.”

No question Marner would be that player. But would he want to come to a team that hasn’t reached the playoffs since 2016? At age 28, wouldn’t it make sense for him to join a team that’s well-positioned to win the Cup?

And while the Red Wings have ample cap space – more than $21 million – so does half the league with the cap projected to increase by $7.5 million to $95.5 million. Many teams can pursue Marner.

Tavares is also a pending unrestricted free agent, coming off an AAV of $11 million. But it makes no sense for the rebuilding Red Wings to spend big on a player who turns 35 in September.

The Leafs aren’t likely to trade Matthews, who’s 27 and scored 69 goals just two years ago. If they did, it would probably cost the Red Wings at minimum, Moritz Seider and Lucas Raymond.

If they can’t land one of the Leafs’ established stars, maybe they’ll look at a potential future star and target restricted free agent Matthew Knies. The 22-year-old, 6-4, 227-pound winger is coming off a 29-goal, 58-point season.

Offer sheets are rare – only 12 have been tendered in the past 25 years. But St. Louis capitalized on Edmonton’s cap crunch to pry away Dylan Holloway and Philip Broberg last summer and reaped the benefits.

“Is it something to consider? Yeah,” Yzerman said of the RFA route. “Do I see us doing it? Probably not.”

Changes are coming in Toronto and Marner is the Red Wings’ best option. But even that seems like a longshot. Still, it should make for an interesting offseason.