I don't expect Shanahan to lose his fans here, but some should atleast question the direction this team is going in trades if this is the best deal this current Mgt team can make with its marquee player. You do not have to be on team Shanahan or other to recognize this. The man is on the job for more than a year now. We should expect better.
If Kessel had 3 years left on his deal, I would agree with you, but you can't ignore the factors that hamstrung the Leafs on this one. I'm not blindly defending them, and am the first to say I'm not happy retaining, giving up a pick, or having lottery protection on the first - but you and others are presenting it as though there were no restrictions to making a deal
How many teams could responsibly fit his contract in long term? Maybe 3 or 4?
How many of those teams would he be willing to go to? 2?
Now - if we were trading FOR Kessel, what would we look at? He's likely to decline halfway through the remainder of his deal? He has known lack of commitment to training?
So you have a market of maybe 2 teams, and you're selling a flawed product. You can't bring him back as he's the poster child for the bad culture you are trying to change. Neither team is wiling to sell the farm, and both want you to retain. You make the best deal for your teams future you can. You add a couple of solid prospects, a young guy who can be flipped at the deadline, extra picks for your revamped scouting staff, $6.8 million of cap space to be creative with, and most importantly, the start of a culture change for your team.
That is how it works in real life.