Shaw's agent, Pat Brisson, denies that he asked for $4.5 million annually for Shaw and said the Hawks just didn't have the cap space to make a deal. However, the compromise that he was willing to make for a lower average annual average apparently came in the form of very long term.
Powers reports that Shaw wanted an average annual value of around $3.2 million, which at seven years would come out to $22.4 million. That's not terribly far off from the $23.4 million he got from Canadiens after being traded, so if the report's accurate he was offering a hometown discount but only slightly.
A $3.2 million cap hit for Shaw might make sense now, but it's risky signing top players for that kind of term, let alone someone who's never recorded 40 points in a season. Shaw turns 25 in July and likely would've been declining well before the end of a seven- or eight-year deal. His physical style may not do him any favors in terms of being an impact player long-term.
So, on the one hand, you have to respect Shaw's side for really trying to find a way to make this work because at $3.2 million, the Hawks probably could've done it. But on the other hand, their compromise would've seen Shaw commanding a $3.2 million cap hit through at least his age-31 season. The Hawks made the right move not locking him down for that long given all their other commitments.
To put it simply: if anyone is getting a seven or eight-year contract from the Blackhawks this offseason, it's Artemi Panarin. That's the kind of player who deserves that kind of term and you have to imagine he's going to get it if the Blackhawks ink him to an extension. And it's the smarter bet, too, because he's younger than Shaw and just scored 17 more points in his rookie season than Shaw over the past two seasons combined.
In the end, Shaw got a better deal in Montreal anyway, too, so while it hurts that he had to go, this seems like an instance where everyone was probably better off.