The Boedker trade was an anomaly, it doesn't need to be cited as evidence of anything. That was the only time the new regime paid that kind of price to send off prospects for what could be a rental. Other than that they sent off individual 2nd round or later picks for players they thought could help them, and almost entirely on players that would be with the team longer than Boedker did.
The problem wasn't necessarily that they gave up those picks. Many teams do the same thing. The difference is most of the players they traded for didn't really help them, as opposed to other teams. Losing the mid round picks was a detriment, but it hurt them because it just expounded on the past bigger mistakes.
Those past mistakes are the REAL problem. Since they started the initial rebuild process, they didn't have a 1st in 2012, and they didn't get an NHL player in 2010 and 2014 with Hishon and Bleackley.
So the real problem is decision making from the previous regime losing their much needed top picks, and the scouting staff (which included the previous director) missing on a couple more top picks.
These are the things that other teams that have rebuilt well have NOT done.
I'm way more critical of the Berra and Gelinas trades than I am the Boedker trade. They lost a 2nd and 3rd round pick on trades that really didn't need to happen. They didn't really need a 3rd string goalie that bad at the time of the Berra trade. Especially one that was a question mark and displayed a lot of inconsistency. Waiting until the summer would have got them a decent backup, and there was word at the time Calgary wasn't even going to sign him.
Gelinas, it was clear was a bad defenseman from day 1. That threw away a 3rd for no reason. Sometimes you need to be patient to evaluate defenseman, but sometimes when a d man is so bad past a certain age, and just has really poor instincts and decision making, it can be pretty obvious. It should have been obvious to to the team.
And the evaluation that Gelinas might be good falls on the pro scouting staff, and really is just another in an incredibly long list of bad evaluations on defenseman. They just are not good at identifying defenseman that will help them. That's a HUGE part of the problem.
The previous regime's decisions to move top picks. The current and previous amateur scouting staff's decisions on draft picks. And the pro scouting staff's recommendations on good defenseman are the problem to focus on.
The Boedker trade by itself is much more a hindsight evaluation. People talk about how important drafting and developing is, but they don't realize this trade was done purely to help develop the young players who's development had stagnated because they didn't get any playoff experience, and gain that knowledge of what it take to win tight games. Just liked Matthias, he seemed genuinely interested in staying and not being a rental. By all accounts it seems they kept their desire to sign elsewhere all to themselves.
Boedker didn't blow the roof off the Pepsi center, but he did what he was expected to in a few games. Be a difference maker and get them some big goals. It wasn't enough to pull them into the playoffs, so because of that it didn't pan out.
On the list of reasons for why the franchise is in the position they are, the Boedker trade is pretty far down, and not really an example of anything since they never really made any other trades like it.