How low will Maple Leafs go before they rise again?

The Toronto Maple Leafs now have 12 picks in the 2016 NHL draft and are just getting started with their rebuilding plan, but they're still going to hit bottom first.

The Toronto Maple Leafs’ fire sale began on Sunday with the trade of pending UFA Shawn Matthias to the Colorado Avalanche for a fourth-round pick in the 2016 NHL Entry Draft and AHL forward Colin Smith. It continued early on Monday morning when the Leafs sent rugged blueliner Roman Polak and forward Nick Spaling to the San Jose Sharks for San Jose’s second-round picks in 2017, 2018 and Raffi Torres.

It was the start of what is expected to be a very busy trade deadline period for the Leafs, who have six more pending unrestricted free agents on their roster. Of course, this was always the plan entering the season: utilize players with one-year contracts, flip them to contenders at the deadline and load up on draft picks. With Colorado’s fourth-round pick, the Maple Leafs now hold a possible 12 picks in this summer’s draft. That’s kind of astounding, especially considering that they’re just getting started.

Maple Leafs trade Polak to Sharks in solid rebuild swap

​It's all an impressive return, let’s be clear on that. Leafs GM Lou Lamoriello should be congratulated on maximizing his assets, but with a three-year contract, you have to wonder if he will even be around to see many of the picks he’s acquired materialize into solid players during his tenure.

The draft is always a crapshoot and while we all know about the litany of talented NHL players who were chosen late in their respective drafts, they are exceptions to the rule. Even if late-round picks do pan out, they often take many years to mature. But Toronto is sticking with its patient plan: a robust rebuild via drafting and developing. To attain those picks, though, you have to get bad before you get better and the Leafs are thick in the weeds of that part of the plan right now. They currently sit second-to-last in the NHL in points percentage. And with the Edmonton Oilers and Buffalo Sabres seemingly content with their young cores, Toronto is the only team this season that is focused on getting worse in the short-term.

OK, so the Leafs are on pace for 72 points this season which would be a slight improvement from their dreadful 68-point performance last season. That’s assuming the team can keep up its pace after the deadline, with three of its top five scorers (Leo Komarov, P.A. Parenteau and NazemKadri) all rumored to be available.

Leafs fans have generally accepted the team’s fate, having bought into the hope that sprouts with the new front office regime in place and highly-touted prospects William Nylander and Mitch Marner in the system. That doesn’t mean things are going to get better anytime soon.

Even if Toronto gets nods of approval for sticking with the plan, this season, painful as it has been to watch at times, might only be a sign of how bad things will get for the on-ice product.

Dion Phaneuf trade a win-win

​With possible entry draft riches on the way and Steven Stamkos possibly available in free agency, this off-season could change a lot for the Leafs. Or, it might not change much. Best case scenario? Toronto wins the lottery and lands top line center prospect Auston Matthews with the first pick, backs up a dump truck full of cash outside of Stamkos’s house and he signs with them, and William Nylander jumps into the NHL with a Calder Trophy-style season. That immediate bump in talent would greatly enhance Mike Babcock’s coaching style and, while they might not contend, the Leafs rebuild would enter the passing lane.

But then what? The best the Leafs could hope for then is a season akin to the one the Sabres are having with highly touted rookie Jack Eichel playing well, but not great and a bonafide no. 1 center in Ryan O’Reilly shouldering the load. Buffalo still sits fourth-worst in the league in points percentage. An improvement, sure, but still a long ways to go to contention. In the long-term, by stockpiling hordes of draft picks, the Leafs could strengthen their organizational depth but this could take much longer than recent three-to-five-year rebuilds.

Worst case scenario? Toronto misses out on Matthews and lands a talented player but one who is not ready to jump into an NHL lineup, Stamkos signs with another team (likely a division rival), Nylander and Marner struggle to adjust to the NHL grind, and Toronto continues to be a landing spot for players who are looking to revitalize their careers on one-year deals.

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And that second scenario won’t include Polak’s presence, Komarov scoring at an otherworldly 16.80% clip, and the leadership of a captain in the locker room. All of this would occur during the Maple Leafs' centennial celebration season.

Pain Is Coming: Mike Babcock goes from killing floor to Maple Leafs

​When the newly hired Babcock warned “There’s pain coming,” perhaps he wasn’t referring to the 2015-16 season in general but the way the Leafs would be after the trade deadline and 2016-17 as well.

It means nothing from a statistical standpoint that this team does, and could, lack an identity for the final quarter of this season and next season as well. But there are players, most notably Morgan Rielly and Nylander, who will be depended upon to lead this team out of the wilderness. That’s a lot to put on an emerging defenseman and a talented youngster with no NHL games in his resumé.

This is part of the plan, though. And we’ll see the most swift part of it come to fruition throughout the next week.

You have to expect that the Columbus Blue Jackets will re-load and try to put this calamity of a season behind them going into 2016-17. If so, it will again be the Leafs who are the only team in the NHL that is purposefully trying to demolish what it has now. With 29 teams trying to get better, the odds in favor of the one team that is trying to get worse now appear to be more stacked than ever.