This graph is flawed and not complete. IMO
Due the rookie performance bonus paid out last year to Matthews, Marner, Nylander and other rookies etc the Leafs have incurred a $5,370,000 (CARRYOVER BONUS OVERAGES) against this years cap.
That $5.37 mil is also dead/wasted cap space that can't be used as part of this years salary cap & added to the Cowan $750k, Gleason $1.333 mil and Kessel $1.2 mil retention = $8.65 mil in dead cap space this year which is likely among the worst in the league.
There was always going to be pain in ridding this team of the cap bind from the previous management group. There was no way around it.
The Shanny/Lou/Babs management team were very upfront that were would be pain and I think they expect it for many more seasons then. But then drafting Matthews changed all of that.
This management team has done an excellent job of getting out from under the horrible cap management of the previous team.
You pointed to the Kessel 1.2M in another post but I'd choose to focus on how we've gained extra assets from good cap management.
Kessel was dealt for a 1st, 3rd and an affordable high end potential Kapanen (1st was used to get our starting goalie).
Winnik for 1 year of cap dump Laich + Carrick + 2nd (Grundstrom)
Phaneuf for a bunch of short term cap dumps (Cowen was a cap credit last year + 2nd rounder who we used to draft Rananen)
Gaining a 4th rounder for taking on Fehr