How is your team in so much cap trouble...?
Brandon Saad- $6mil. 23 years old and scored 31 goals this year. Good contract.
Brandon Dubinsky- 5.85mil. 50 point player, grit, leadership, something. Not good contract.
Nick Foligno- 5.5mil. scored 30 goals one year and was given contract assuming he will remain captain and keep the same kind of production. He will not.
David Clarkson- 5.25mil. Shambolic contract that has to be eaten because Horton's borked back, insurance fine print, and a small market ownership who don't want to eat the salary. Yeah, it is what it is.
Scott Hartnell- 4.75mil. Traded for Umberger so BJs could get better player at similar price and Flyers could get a shorter contract. Hartnell's production actually justifies the contract. Go figure.
Seth Jones- 5.4mil. Good contract. Good job front office.
Jack Johnson- 4.35mil. Fancy stats hate him. Normal stats hate him too. Not good.
Savard- 4.25mil. Contract based on locking down potential top pairing D man before he gets too good and demands more. He is not a potential top pairing D man.
Bobrovsky- 7.425mil. Given 2nd highest goalie contract two years removed from Vezina, one year removed from playoffs. Has since regressed and become more injury-prone. Looking ugly.
So yeah, a mix of bad luck and overvaluing mediocre talent and a couple good contracts sprinkled in there.
At the end of the day the cap hell is there because of Horton's back, Bob regressing, bad Foligno+Dubinsky contracts, and bad Savard+Johnson contracts.