As the calendar turns to 2023 and teams approach the halfway mark in their seasons, focus starts to shift towards the league’s trade deadline, set for March 3rd. That might feel far away, and in terms of a team’s season it is, but in reality it’s just two months away. Earlier, TSN’s Pierre LeBrun, Chris Johnston, and Darren Dreger convened for today’s Insider Trading segment, where the group discussed a number of topics related to not only the upcoming deadline, but team’s strategies approaching their builds, their assets, and how they’ll manage the next two months.

There’s always the odd trade or two in the months leading up to the deadline, but it seems most business gets done in the few days before and the day of. So, why would we expect any different this year? As LeBrun points out, the answer may lie at the forefront of Canada’s World Juniors performance: Connor Bedard. Every team would love to have the phenom, but presumably only the winner of the Draft Lottery will have the opportunity.

LeBrun explains that the Bedard sweepstakes could push teams to trade players earlier, perhaps even in January, in order to fortify their chances in the lottery. In other words, though teams are hesitant to use the word “tank,” if that’s their mission, getting the talent that might win a few games off the roster sooner than later could sink the team even lower in the standings than had they waited another two months. LeBrun says these conversations are certainly happening, but cautions that with the sellers, the buyers need to agree too, but the buyers must deal with a tricky cap situation. With salary cap space growing as time moves on, the teams in the market for those rental players might not be able to make the move they want until closer to the deadline.

Generally, the hot commodities at the deadline are the talented rental players, which explains why so many teams pay the high prices for them. This year, that will likely hold true, but another hot commodity will be first-round picks. Even beyond the chance to win the draft lottery for the 16 eligible slots, the 2023 draft is expected to be deep, inflating the value of all first-round choices to an extent. Thus, those picks will be in high demand, says Johnston.

In fact, Johnston says shutdown defensemen like Joel Edmundson of the Montreal Canadiens and Vladislav Gavrikov of the Columbus Blue Jackets, could both fetch their teams a first-round pick and then some. Surprising as that might sound, consider last trade deadline when Montreal was able to secure a first-round pick (and more) for veteran defenseman Ben Chiarot, then a pending UFA. Here, the 29-year-old Edmundson is under contract for another season at a very affordable $3.5MM AAV, while Gavrikov, a pending UFA, is considered one of the league’s best shutdown defenseman and is just 27-years-old himself.

Also of note on Gavrikov, Johnston adds that the struggling Blue Jackets still haven’t determined if they’ll trade him or not. Columbus of course isn’t necessarily hoping to get into the playoff race this season, but could hope to re-sign the blueliner for themselves.

One rather interesting team heading into the deadline is the St. Louis Blues, who came into tonight with a 17-17-3 record. The team recently placed star forwards and pending UFA’s Ryan O’Reilly and Vladimir Tarasenko on IR, joining defenseman Torey Krug. Dreger notes that Blues’ GM Doug Armstrong doesn’t feel pressured to make a decision on what to do with either O’Reilly or Tarasenko, or his trade deadline approach for that matter. Instead, the organization will consider the trade value of their pending UFAs against the idea, and likelihood, of extending them.

There’s no doubt that either O’Reilly or Tarasenko would bring a large haul back for St. Louis, however trading either could foreclose any chance of bringing them back next year. That would be a tough loss, or losses, for a team still looking to compete and probably a bit surprised at their lack of success this season.

A final note, also from Dreger, is the status of the Chicago Blackhawks’ pair of franchise players: Jonathan Toews and Patrick Kane. Both are pending UFAs and both rumored to be on the move this winter. Dreger expects Pat Brisson, agent to both players, to engage in serious talks in the near future with each to determine the following: Do they want to be traded? If so, what does the contending field look like? And, would it be best to accept a trade, then look at the open market come July, or is a trade-and-sign an option?

As tough as it will be to move on, the Blackhawks will hope both players can be moved for a large return. However, both control their destiny, having complete no-move clauses, so a trade will not only be up to Chicago and their trade partner, but the player themselves.