1) Anders Lee (3 years, $7 million AAV)
Now this is was and remains a more complicated situation.
On the first of July in 2019, the Islanders and their fans woke up to the realization that Artemi Panarin had decided to go across town to join the Rangers rather than come to Long Island. This was also only one year after the Isles had lost their franchise player, John Tavares, to free agency. It would have been a tough pill to swallow if the Islanders let their captain walk in consecutive off-seasons.
Lou Lamoriello made the decision to make sure he kept Lee around long-term, but it was always likely that the Islanders would pay for it on the back end of the contract. Since signing the extension, Lee has still produced at a high level, scoring 28 goals in each of the last two seasons, but just isn't a dynamic offensive player compared to others that carry a $7M AAV cap hit.
For reference, DeBrincat's contract with the Red Wings will have him making a little under $8 million in each of the next four seasons. Lee has been a big part of the Islanders' success over the last decade, but it seems fair to say that he, at the age of 33, should not be making similar money to a 25-year-old who's already had two 40-goal seasons.
Then there are players like Winnipeg's Kyle Connor, that carry a cap hit of $7.5M AAV cap hit and put up over 90 points last season. Buffalo's Tage Thompson signed a 7-year, $50M extension with the Sabres last August and produced a 47-goal, 47-assist season.
Lee has been an excellent captain since he became the leader just before the 2018-19 season, but his cap hit is among the reasons the Islanders find themselves handcuffed when trying to make roster improvements due to salary cap issues. He is still doing Anders Lee-type things and scoring Anders-Lee-type goals but appears a step slower and is a one-dimensional player that doesn't help you win if he's not scoring goals in front of the net.