TL;DR at the bttom. Sorry for the delay. It is a false premise, but one I'm comfortable making on the basis of both contract/cap management and probability for the following reasons (long post - hopefully grammar is well enough, don't really have time to proof as I'm at work):
The majority of teams manage cap like a short term prepaid expense, rather than a long term investment. This is a result of different goals over different time horizons, and I'd argue the $AAV (cap hit) amount of individual contracts is less important to a GM than the overall liability at a given time. Term is more important than $. PV principals apply to the cash outlay of NHL contracts, but the NHL does it backwards - this is true because most contracts are front-end loaded. Present value of money is that it is worth more today, than in the future. So although the cash going out in the early years of the contract is higher and this is bad from a PV perspective, minimizing cap space each year increases the likelihood of receiving as much money back as possible from escrow. Since most GMs try to minimize cap space, it benefits the league in the short term as more money is recovered on aggregate (since most teams are above the midpoint, and this year obviously revenue got chunked - obviously the HRR/escrow calc is more onerous than presented here).
Team aggregate cap is made up of a bunch of tranches (levels of contracts) based on time remaining on contract - Time = 1, 2, and 3, up to a maximum of 8 years. Looking at contracts by payback period, where the value being paid-back is on ice results or some other metric which is non-monetary. Most NHL contracts should maximize payback over the first half of the contract, where the player is hopefully in their prime and at their most productive. Going back to the PV, you should be able to get away with higher upfront costs if - ("value received" > Current cash - escrow recovered). Obviously this analysis will be dependent on what exactly you use to measure value - whether points, advanced stats, etc. If you have maximized your value when the cash outlays are high in the short term, then the contract is easier to sell in second half of the contract, since by a PV method - ("value received" > Current cash - escrow recovered) - should still be true for the team buying the contract.
EDIT - I do want to add in the tranche management is more important than individual contract management - because it denotes the expected liability year over year, which is super simple to forecast. Since the aggregate liability cannot be less than the cap floor, bad contracts here or there are not going to ruin cap management on their own. Tranche management also gives you more visibility regarding ELC, RFA, UFA needs - since these are all different types of contracts and carry different risks (Arbitration, age, etc). Contracts should be viewed in aggregate long term, and individually short term. It's a weird balance.
per this source -
Pittsburgh Steelers, Penguins, Pirates News, Live Coverage | DK Pittsburgh Sports - average escrow was 9.5% 2018-19. For the below, assume NHL recovered 100% of the escrow and it was the same for last year. Escrow is withheld on the cash payment, not a cap hit basis.
Simple Example - Connor McDavid (19-20 cash outlay = 14M, cap hit = 12M) Age = 23
9.5% of his cash outlay was 1.33M.
So for Connor McDavid - was the value received by the franchise > 14M - 1.33M last year? This can be through sponsorship, merch, on-ice results (top 2 in points), etc. I would argue yes, arbitrarily it was (Obviously you would a better definition of value received, were you to do the analysis for real).
This contract will expire when he is 28 years old and at age 26ish, the cash outlay is 11m, which is 1m less than the cap hit. Using the same calc and assumptions, would this contract be worthwhile to buy? IE - will the value received by the team buying the contract > 11M - escrow. The answer is probably yes, so this would be a favourable contract. Obviously this is super simple for the top 3 player in the world over the life of his first RFA contract, who is also young and in his prime. You can see some instances where this might not be true for players who are 30 and the value being received is already dipping. A contract like Weber might actually still be worthwhile to buy near the end, since actual cash in the end of his contract will be 1M. Although the cap is extreme (7m) and his value as a 40 whatever old might not be good, the questions - will it be worse than 1M less escrow? Maybe not. This is why we see places like Arizon and Ottawa collect these contracts. Obviously most of this intuitive at first glance.
What this has to do with my point is - The goal of short term (yearly) cap management is to maximize ROI, where the investment is fixed anywhere from the cap floor to the cap ceiling. Each year you measure what value is being returned against the basis of this years cap hit only. Every year it changes this changes as contracts slide in and out of positive value and new contracts are signed. Accumulating as many positive value contracts is the start of recognizing good ROI year in and out. This can be as simple as singing Joe Thornton for league minimum to sell jerseys and make money - is he going to provide the push to create playoff gate revenue? The Leafs already create gate revenue on their own, so no. However, it is a positive value contract for the Leafs. Last year - Tyson Barrie was not, since anyone can probably tell you that his on-ice value received was less than the cash outlay.
However, the goal of long term cap management is to minimize future liability, since you don't want to become over-levered on contracts which start to show negative ROI in the
current short term (from the perspective where "current" refers to years 6, 7, 8, 9). If the contracts have positive value in the later years, they can be offloaded, but in cases like Lucic, Eriksson, etc - they cannot be sold without short term losses (draft picks, etc - see Marleau). Unless a contract is heavily skewed with front loaded payments, most contracts will start to show negative value near the end, since a players on-ice value generally drops quicker than the backend payments of a front-loaded contract. This is dangerous in the short term since front loading too much leaves you vulnerable to heavy recapture, and it's harder for the contract to be positive in the beginning. NHL also has rules about how far the expenditure can be from the AAV to avoid this stuff.
These are incongruous goals - the short term goal of minimizing cap space to fill out the roster since cap space expires every year + getting a mulligan from escrow VS trying to leave room to replace contracts you can't forecast for and avoiding dead weight down the road - like a Pettersson, or Draisaitl, etc. GMs also face pressure from the fans or the media if they sit around letting 8m of cap space go to waste every year. All of these things together, IMO, result in every team having at least one bad contract - it's inevitable that something you signed in the past will at some point no longer have positive value. Rarer occasions like a Josh Anderson contract exist, where the contract might not even have positive value the day it was signed. With these principals in mind, it's actually not a guaranteed failure that Dubas signed Matthews/Marner to shorter contracts - which is something many people hold against him. It goes against the prevailing school of thought, that young kids should automatically be locked up with the key thrown away, but from a financial point of view - it does de-lever the org in the mid term. I'm on the fence whether they are bad contracts from a "value to the org" point of view - since the Leafs make tonnes of money off those guys, and they perform well. However - if you don't look at income generated from the players, the Marner contract is a candidate for a bad contract. Depends what you use to define - "value received", which is subjective based on the goals of the organization. Like it or not, the goals of the Leafs may not be primarily to win a cup, it may be to maximize revenue; with the exception of on-ice results, these teams do not compete against each other in business. They are all in the same boat together - so having orgs like the Sens who clean the tank and inherit high cap hit, low dollar contracts is a good thing, it allows orgs like the Leafs to offload these high cap contracts and sign high dollar contracts - which help to increase escrowed amounts. The Leafs also like to clean up a lot of LTIR garbage for the league, it's very much like a big fish tank.
TL;DR -
The short term goal of minimizing cap space to fill out the roster since cap space expires every year, where you also get a mulligan from escrow
vs trying to leave room to replace contracts you can't forecast for - like a Pettersson, or Draisaitl, etc. GMs also face pressure from the fans or the media if they sit around letting 8m of cap space go to waste every year. All of these things together, IMO, result in every team having at least one bad contract - it's inevitable that something you signed in the past will at some point no longer have positive value. It's also possible IMO to have bad contracts that are 2 years, rather than the general feeling where people say - "term isn't bad, so there's no risk".
To answer your question about Boston - the David Krejci contract is bad. It's not the worst contract in the league obviously, but compared to value received from him versus the value from the top line players, who are all signed for less - I think internally that's a bad contract.
