Another good article on what is taking so long(Flamesnation):
http://flamesnation.ca/2016/7/18/gau...-s-complicated
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Each player's representatives have an incentive to have their deal expire juuuust a bit before the other one does, as that way they would have the opportunity to get their big "Please don't go to free agency" raise before the other guy does (and effectively get the maximum piece of the Flames salary cap pie rather than negotiate against each other). That's probably something that plays into it.
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The current CBA can potentially expire at the end of the 2021-22 season and agents are understandably wary about salaries being rolled back. So, we've seen the rise of something known as "Lockout Proofing." Rather than paying out the $7.5 million equivalent to Gaudreau every season in salary (for example), the sides could negotiate a combination of salary and signing bonuses. Salary can be rolled back, but bonuses can't. So the amount paid out each season and the composition of what is paid out is a huge factor in current negotiations league-wide.
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