Brendan Gallagher
It's hard to include Gallagher on any of these lists as his commitment to the Canadiens has made him a fan favorite. He joined the Canadiens in 2012-13 and made an immediate impact, but injuries have caught up to him in recent years.
The last time Gallagher played a full season was in 2018-19, tallying 33 goals and 19 assists. The next four seasons included 59, 35, 56, and 37 games. (Keep in mind there were some pandemic years where the seasons were shorter.) He finally maintained his health last season, appearing in 77 games. However, he had just 16 goals and 15 assists.
Gallagher will make $6.5 million annually for the next three seasons. If his production continues to decline, the contract could get ugly by the end of the deal.