Likely the only way he could get him to buy 1 year of UFA status was by offering this. I don't think he contact is that bad. Had the cap continued to rise at the rate it did and we had no Covid, alot of these contracts signed prior would look like very solid deals and maybe even team friendly.
Covid and the stagnant cap for the past 3 years really hurt of lot of contact perception.
The contract was a massive loss for the franchise the instant it was signed. The 5 year term coupled to a top 3 salary was miles away from what the RFA market had been over the preceding decade. The flat cap made it worse, but only getting 5 years instead of 8 significantly reduced the benefit you expect to get from cap growth.
The Leafs needed to draw a hard line in the sand on some aspect of the deal and they failed to do so. If Matthews was going to become the 3rd highest paid player in the league, then they had to demand that the contract would be a max term deal. If Matthews wasn't willing to sell 4 UFA seasons, then they had to demand that he not receive superstar UFA money.
At the time he signed his deal, every single forward in the NHL with an AAV of $7M+ got their contract by signing away 3 or more UFA years.
Steven Stamkos is the only player in the preceding decade who became a top 20 paid forward in the NHL without signing away 3+ UFA years. He signed a 5 year deal (with a NMC in year 5 just like Matthews did. However, his $7.5M AAV was 11.66% of the cap while Matthews' $11.6M AAV was 14.64% of the cap. Stamkos was tied for the 8th highest paid forward in the NHL and it is worth noting that he already had a Rocket Richard trophy (and a 2nd place finish) while Matthews had a 2nd place finish and no other top 5 finishes. Stamkos was a more accomplished player than Matthews at the time they signed their 5 year deals but the Leafs paid a significantly higher premium. The Stamkos $7.5M would have been the equivalent to $9.27M at the time Matthews signed his extension.
That was the absolute most player-favorable comp of the last decade and it was 8 years old. Even if the Leafs had allowed the agent to ignore the most recent 7 years of the RFA market and demand that Matthews be paid like the most favorable comp from the last decade, this had to be the line in the sand on a 5 year deal. Hell, round it up to $9.34M AAV to get the player's number into the AAV and give him bragging rights over Stamkos. That would have been an exceedingly reasonable line in the sand to draw on a 5 year term. If the player balked and kept demanding the $11M+ AAV, then you counter by saying that you're happy to go there, but only on an 8 year term. Eichel had recently gotten $10M (13.33% of the cap) and it took 8 years to get it. McDavid recently got $12.5M (16.67% of the cap) and it took 8 years to get it. Meeting in the middle ($11.25M or 15% of the cap) would have been plenty reasonable
if the player took the same term that they got.
Giving Matthews the best of both worlds (and structuring it to be essentially all signing bonus) was a massive loss in negotiations. It was feasible to build around the AAV given the skill of the player, but it potentially shrunk the competitive window by 3 years. If it doesn't shrink the window by 3 years, then it means that the team will have to absorb an even bigger cap hit for those 3 years to avoid the player from walking. Because he sure as hell is going to get a raise starting in 2024/25.