The Leafs have a very unique opportunity to do something shocking at this year's trade deadline

So, hypothetically, if the Leafs were to opt out of the buyer's market before the deadline, would you be fine with them standing pat while in win-now mode? That's a million dollar question, but perhaps the even more intriguing question is this; should the Leafs become sellers and use some of their expiring contracts as trade bait for contending teams in order to fetch some additional draft capital and/or prospects?

The Leafs have a number of players on expiring deals who could certainly yield a handsome return, if that's the route that Brad Treliving and the Leafs choose to go. Just a quick glimpse at the Leafs' CapFriendly page shows a tremendous amount of players on expiring deals who could, at the very least, bring back a draft pick. Some would bring back even larger returns.

Take Tyler Bertuzzi, for example. If the Leafs aren't sure that they're going to be true Stanley Cup contenders this year, and if they don't feel as though they'll be able to re-sign Bertuzzi in the offseason, you'd have to imagine that if they opted to retain salary on Bertuzzi, they'd get a pretty solid return of futures and draft capital.

Max Domi, Ilya Samsonov, T.J. Brodie, Bobby McMann, William Lagesson, Martin Jones and Mark Giordano represent the pending UFAs on the team. Nicholas Robertson, Simon Benoit, Timothy Liljegren and Noah Gregor represent the pending RFAs in the group.

Obviously, there are a number of players that the Leafs may want to retain, such as Liljegren, Benoit and potentially Jones. If you want to include Bertuzzi and Domi on this list, then great. It still leaves the team with a number of enticing options for other teams who may be willing to part with a draft pick.

The Leafs have 9 draft picks in this year's draft, but 7 of those picks will occur in rounds 4 or later, leaving the Leafs with only their 2024 1st rounder and the Islanders' 3rd round pick in the first 3 rounds. Moving someone like Robertson, for example, may bring the Leafs back a 3rd round pick. If a team is looking to bolster their top-4 ahead of the playoffs, I'm sure someone would part with a 2nd round pick for defensive specialist and PK wizard T.J. Brodie.

If the Leafs opted to move Bertuzzi to a contender at, say, 50% salary retention, I'm sure they'd have no problem bringing back a late 1st round pick and a prospect or even multiple draft picks.

There are still options for the Leafs outside of selling off the farm in order to try to win now with a subpar group. If this doesn't feel like a year in which the Leafs can win or even compete, what's the use in emptying the cupboards for another 1 round win? Or even a 1st round exit?

The Leafs have a chance to do something rather unique here. That is to keep their core intact and ship off supporting cast for pieces and parts to help them next season and in the future, which could maximize their potential during the first season of Nylander and Matthews' new deals. What's wrong with setting up for future success if you aren't sure about the present? Just my two cents.