Since I started covering the Colorado Avalanche in some form back around 2009, the Avs have had two first-round picks as many years as they’ve not had a first-round pick at all.

That is to say, it’s happened twice, back in 2011 when the team selected Gabe Landeskog and Duncan Siemens and 2019 when they took Bowen Byram and Alex Newhook. Following yesterday’s trade of Newhook to the Montreal Canadiens in exchange for picks 31 and 37, the Avs are once again slated to pick twice in the first round at 27 and 31.

Now, the organization is in a little different place than back then. The extra selections were from the Erik Johnson and Matt Duchene trades, respectively, and this was a team still trying to find its way. Today, they are recent Stanley Cup champions trying to find their way back to the mountaintop.

That’s what makes walking into this NHL Draft so different. If you polled every NHL executive in the league, I would be willing to bet very few of them believe the Avalanche are going to make both of those selections. Colorado just traded a 22-year-old player who, while failing to meet high expectations, still managed back-to-back 30-point seasons and was a productive member of the lineup and wasn’t going to break the bank on a new contract this summer.

Aggressive moves over the years have seen the Avs trade draft picks and/or prospects for the likes of Andre Burakovsky, Devon Toews, Philipp Grubauer, Darcy Kuemper, Alexandar Georgiev, Josh Manson, Artturi Lehkonen, Andrew Cogliano, Colin Wilson, Vlad Namestnikov, and Derick Brassard, among others.

The team has turned many of its draft picks into solid contributors, key role players, and three different starting goaltenders on three different division-winning teams before ever using them on the draft floor. While their draft and development results have left a lot to be desired, their ability to scout the NHL and get quality play out of draft pick exchanges has been among the league’s best over the last five years.

Colorado has gotten so good at this particular part of player acquisition that people frequently joke that if you get a call from the Avalanche front office, you either don’t answer or find out who they’re interested in and figure out what you’re missing. Whatever you do, don’t trade with them.

Well, Montreal’s Kent Hughes jumped into the ring and gave the Avalanche two more draft picks to play with over the next 24 hours. I’m sure the front offices in Edmonton, Vegas, and every team in the Central Division that cares about winning (so not Arizona and Chicago…yet) were rolling their eyes at the thought of what the Avs might do with that kind of draft pick capital to play with.

As Colorado’s star players have graduated from cheap contracts to needing to get paid premium prices for being premium players, the need for the Avs to find cost-efficient players elsewhere on the roster has gone up.

We saw last year the team failed to adequately replace Nazem Kadri despite an admirable attempt by J.T. Compher and the lack of center depth was one of many factors that led to the team’s disappointing first-round loss to the Seattle Kraken.

Colorado addressed the 2C spot earlier this week with the extremely cheap acquisition of Ryan Johansen, but it still has the rest of a roster to fill out and only in the neighborhood of $15.5 million to do it. They still need a second-line wing to round out their top-six forwards and, with the trade of Newhook, need at least a third-line center and, depending on how they feel about Ben Meyers, a fourth-line center, too.

The departure of Erik Johnson also opens up a spot on the defense that needs to be filled next year and until he signs a new contract, there will be uncertainty around just how much money Bowen Byram is going to make this season.

There’s work to be done here as the Avs enter this evening’s first round of the draft. Should the Avalanche decide to simply sit tight and make their scheduled picks at 27, 31, and 37, Colorado’s prospect pipeline would get a desperate injection of youth and skill. The Avs have only made six selections over the last two years in the draft and their highest pick last year was 193rd overall.

After the 37th pick, Colorado’s next pick this year is scheduled to come in the fifth round at 155. If the Avalanche wants to give its prospect pipeline a boost, sitting back and making the picks is the way to go. Hell, maybe they’ll even trade down once or twice to try and add a few more picks. Why not try to add a future second or third-round pick while they’re at it? If they’re going to use this draft to replenish their draft capital, go all the way with it.

If they choose to do that, it’s realistic that whoever the Avs pick won’t be pushing for the NHL team until 2026 or 2027, and even then it’s fair to wonder if the Avs will be able to integrate the young player into the lineup.

You see, the Avs have been hailed as this success story of drafting and developing the right guys. In a way, it’s true. Landeskog, Nathan MacKinnon, Mikko Rantanen, and Cale Makar are all very likely going to have their numbers retired in Ball Arena someday and were draft picks of the team. Maybe Byram gets added to that list, too, but the reality is that those guys all showed when the Avs simply had no better players to take those jobs.

Since then, we’ve seen the team fail to successfully integrate Conor Timmins (there are mitigating circumstances here, I realize, but it’s still true), Martin Kaut (the 16th pick in the 2018 draft), and other top-100 selections in Sampo Ranta, A.J. Greer, Nicolas Meloche, and J.C. Beaudin. All but Ranta have gone on to play in the NHL for other organizations.

If the rebuttal is to ask how good any of those players were in the first place, that’s fair. There is maybe no blurrier line in sports than the one that exists between draft and development. It’s a chicken and egg question, no doubt, but the reality is that the Avalanche has been by far the worst in the NHL at this over the last ten years.

The one success story has been Logan O’Connor, an undrafted player out of the University of Denver who had the extremely rare path of being a more productive AHL player than college player and has carved out a role in Colorado’s bottom six as a valuable depth forward. His success has led the Avs to more aggressively mine the college ranks for more mostly-developed players (see: Ben Meyers and last year’s signing of four undrafted college players to contracts. Meanwhile, 2020 sixth-round pick Nils Aman, unsigned by the Avs, played 68 games for the Vancouver Canucks).

Like Newhook, the team struggled to get what it wanted out of Tyson Jost, the 10th pick of the 2017 draft, before ultimately moving on. Jost seems to have found a home in Buffalo for now as a depth player, but it’s become a worrying trend that the Avs can’t seem to balance the need to develop players alongside the drive to win at the highest level.

They hit grand slams with the selections of three potential Hall of Fame players in MacKinnon, Rantanen, and Makar. Those are the pillars of Colorado’s success (the new Sakic/Forsberg/Roy if you will) and as long as they’re on the same team, other teams will be nervous about the damage the Avs can do.

But will any of Colorado’s rivals be scared if the Avs simply sit back and use all three of these selections? I’m venturing to guess the answer is an emphatic no, to the point where I bet all of them will breathe a sigh of relief if the Avs don’t have something else up their sleeve before they leave Nashville on Thursday night as they prepare for the open of free agency on Saturday morning.

That’s what makes this such a pivotal moment in this timeline of Avalanche hockey. Will the Avs push the right buttons, and continue their tradition of finding exceptional value through the leverage of trading draft picks for undervalued NHL players? Or will the Avalanche play it perhaps too patiently and make a couple of picks and go into the weekend with all the same needs they have right now but with three drafted prospects, whose value immediately plummets the second they are selected a la buying a car and driving it off the lot.

It’s not to say the Avs won’t be able to use those players in deals later. Timmins, Drew Helleson, and Justin Barron were all once in the Avalanche organization at the same time and all three are slated to play for different NHL teams next year. The Avs can still make it work, the job just gets that much harder when you actually select a player.

So what do the Avs have in store for the NHL? Are they the wounded juggernaut so many believe them to be after their title defense was submarined by an endless parade of injuries and comically bad luck? Or was their run to the Stanley Cup the best this core had to offer?

How the Avalanche handles the next 48 or so hours will play a major role in determining the answer to that question.