This off season I think we are finally seeing Sweeny's biggest strength, contracts, become a liability. Sweeney very cautious about entering big money long-term deals. This paid off big time in probably his best move, which was trading Lucic for a huge haul (regardless of how he used it) and avoiding a killer 7X6 contract. Now, it is clear that Sweeney is actually too conservative with contracts, and is approaching Harry Sinden territory. We have cap space, there have been good players available via trade and free agency, prices are reasonable, yet we have let talent go rather than acquired it.
Sweeney was brought in largely because of an impression that Chiarelli mismanaged money and gave out too many big contracts. The irony is that none of those Chiarelli contracts look bad 5 years after he as fired. Bergeron, Krejci and Rask are still on Chiarelli contracts and performing at or above their contract price. Chara's long-term contract, which look like it might turn bad, expired long ago and he keeps getting extended. Likewise, in Edmonton, Chiarelli's long term contract for Draisaitl, sort of shocking at the time, looks downright brilliant.
At some point, we need to pay FMV for talent. Sweeney rigidly sticks to an internal cap structure, which is fine when setting a line for RFA's, but won't ever get you a player on the UFA market.