1) Sure, get full value for the player. In 2014 pundits were talking about how Kane was droolworthy because of his decent long term deal and his scoring chops. Was no one interested or was Chevy asking too much?
2) ...Or was he asking at all? Is there any evidence that Chevy was really trying to deal Kane? A guy wants out for 3 years and with 29 potential dance partners and Chevy just can't make it happen? But then he has him gone in a week after the tracksuit incident with 1 dance partner and Kane on the IR for the rest of the season? Sorry - I just can't do those kind of mental gymnastics...
3) I'm sure players understand that having a trade demand met within a week or two is unreasonable (except in the case of the tracksuit incident where things somehow came together incredibly quickly) - but 3 years? In a situation you hate, with few friends in the locker room. Does this seem reasonable to ask of a professional? Kane showed up to every game, played hard, didn't go obviously public with his trade demands (though he didn't hide it terribly well)...Chevy sits on his hands for 3 year. Who's the professional again?
4) Right - who cares if Chevy's a jerk when the team is winning? Oh wait - 1 playoff year in 5 (and he sort of dismantled the team that had that 1 good year). He's also the guy who signed the terrible goalie that's been holding the team back too.
Anyway, I'm not even saying Chevy didn't trade Kane for 3 years to be a jerk - maybe it was dithering or incompetence.