The Toronto Maple Leafs lost to the Florida Panthers in the second round of the Stanley Cup Playoffs. It marked the end of an era for various reasons, including the departure of team president Brendan Shanahan. But NHL free agency will be fascinating for the Maple Leafs, as star forwards Mitch Marner and John Tavares are both available. Losing half of the Core Four would be disastrous for Toronto and its new executives.
Both Marner and Tavares are from Ontario. That isn't that impressive, as seemingly half the league is from Canada's densest province. But they have both made that a key part of their Maple Leafs tenure. They grew up Leaf fans, wanted to bring the team to glory, and failed epically in seven straight playoff appearances for Tavares and nine for Marner. Now, they may both leave, and general manager Brad Treliving does not have a backup plan waiting in the wings.
There are legitimate reasons why Maple Leafs fans are frustrated with Tavares and Marner. They both disappeared in big games, see Games 5 and 7 of the Panthers series, for example, and they never made the conference final. But at this NHL trade deadline, they went all-in, trading prospect Fraser Minten to the Bruins for Brandon Carlo. Losing both would leave two gaping holes in their top six without a true replacement.
Marner and the Maple Leafs appear to be on the outs, with the front office asking him to waive his no-trade clause at the deadline. Considering his massive pay day that will be coming, they may want to steer away. But that means Tavares needs to stay after another solid regular season to help usher Easton Cowen, their new top forward prospect, into NHL games.
The Maple Leafs also must avoid a division foe

If the Maple Leafs were to lose Marner and Tavares, they could hit NHL free agency looking for a replacement. If they brought in Nikolaj Ehlers or Brock Boeser, that would make sense. But too many fans and pundits believe Sam Bennett is the key to the Florida Panthers' success. While he is an important player for them, overpaying Bennett could cost a team a legitimate Cup window.
The Maple Leafs saw firsthand how important Bennett is to the Panthers. His up-to-the-line physicality knocked Anthony Stolarz out of the series without drawing a penalty or suspension. Fans who believe that the Leafs need to get more physical to win in the playoffs aren't necessarily wrong, but overpaying for that is where teams get in trouble. Milan Lucic's Oilers' contract, Dave Bolland's Panthers deal, and the deal the Leafs gave David Clarkson in 2013 should be enough proof to not overpay Bennett.
This free agency period will be a tough line to toe for Treliving. It is a disaster if they lose Marner and Tavares, overpay Bennett, and think that they're a better team because of it. Keeping one of Marner and Tavares, supplementing them offensively with Cowen and a lower-priced free agent, and maybe adding a defenseman, could be the path for Toronto.
Brad Treliving has given out some historically poor contracts in his tenure as an NHL GM. Jonathan Huberdeau, James Neal, and Troy Brouwer are just some names that haunt Flames fans to this day. He also let Johnny Gaudreau walk for nothing and fumbled the Matthew Tkachuk deal in Calgary. How did Bennett become a playoff stud for Florida? By getting traded there from Calgary when Treliving was in charge.
This offseason is Treliving's first big test. It could set the Maple Leafs on a more successful path than the one they were on. It could also set them back, costing them years of Auston Matthews' prime. What are the right and wrong moves for the Maple Leafs this summer?