This season's trade deadline is fast approaching, set to come to a head next Monday afternoon. While it typically represents a pivotal point on the NHL calendar annually, it remains to be seen how much real action we'll actually even see this year.

Even under ideal circumstances, the league will never be mistaken for one that's pushing the envelope to orchestrate blockbuster trades. What we typically see instead, is relatively safe tinkering on the margins. Teams add third-pairing defensemen and penalty-killing bottom-six forwards, and we're left blowing their potential contributions out of proportion because it's all we've got to work with.

This season is undoubtedly anything but ideal for obvious reasons, and all of the added financial considerations seem like a major obstacle standing in the way of impactful trades right now. Whether it was the last free agency period when players were settling for discount rates or the various useful players that have been shuttled through waivers without any takers this season, it's clear that the large majority of teams are either unwilling or unable to take on money.

For a lot of teams, the question of whether it's even worth trying to make a push this season is a very real one. We know that the NHL playoffs can be random, and you just have to make it to have a chance. But the idea of finishing fourth in the West or Central right now, and earning the right to be fed to either the Avalanche or Lightning in round one isn't an especially appealing one. Particularly without the added benefits of the typical revenue of home playoff games with fans in attendance. With significantly more sellers than buyers, and financial flexibility tight for everyone, it's tough to markedly move the needle with any manoeuvering.

But we're not going to let that stop us from daydreaming and trying to manifest trades by putting them out into the universe. In preparation for Monday's deadline, we're going to take a look at the teams that should be trying to add right now, and who they should be targeting to address whatever needs they may have.

For the purposes of this exercise, we'll focus on players that are presumed to be available according to trade boards. While it's fun to be spicy and speculate about how prudent it would be for a team like the Blue Jackets to be proactive and trade Seth Jones while there's term left on his deal, or the Flames to sell high on Sean Monahan while people still think he's good, the likelihood of either happening is next to none. So let's instead focus on players that are realistically going to be moved, and where they would be the best fit. 

On a personal note, this is one of my favourite exercises to do every season. Not only is it fun to try to figure out what's going to happen beforehand, but it makes for a great bit of revisionist history after the fact. I'd like to think that we've enjoyed some pretty good success doing so over the years. Last deadline we nailed the Robin Lehner to Vegas move, and the year before we were on the right track with a couple of other big trades. Let's take a look at what we've got to work with this season, and try to play the role of matchmaker again.