You had me...and you lost me.
ha, most NHL teams are run by smart people*
Why do you think Chicago was so competitive for so long and won 3 cups and 5 western conference finals to see them now at the bottom? Its because you pay the price for success. Teams don't just think about being competitive , if they feel this is their time they will understand certain sacrifices.
Toronto is a young promising unproven team , Matthews, Tavares are great but unproven , you need a mixture of players whom bring that type of experience to help with taking the next step.
Keith's numbers are just as good anemic not better than the defenseman Toronto already has and he isn't showing any signs of slowing Down.
Toronto's cap situation isn't going to get any better and GMs know that so if their shot is this year or worst case next year Keith would make sense and would be highly effective and targeted.
Chicago was successful because of the core they drafted, but let's look at the type of additions that they made when their core players were the same age that Toronto's are now:
Locked up Patrick Sharp to a 4 year contract @ $3.9M per to support their longer window of opportunity
Locked up Keith to a 13 year, $5.5M AAV deal that would be cap circumvention today, buying all of his UFA years knowing that it would be a bad contract at the end but securing all of his prime years at a very affordable rate (36yo Sergei Gonchar got $5.5Mx3 years for all non-prime years in the same free agent class,
Locked up Hjalmarsson to a 4 year contract to support the primes of their core players
locked up Seabrook to a 5 year contract to support the primes of their core players
locked up Brian Campbell to an 8 year contract for the same reason
Added Marian Hossa, 30 years old on a 12 year contract at an AAV of $5.275M. This would be cap circumvention today, but they got Hossa at a very good cap hit (about $2M less than market, 27yo Gaborik signed the same year at $7.5M as a UFA for example) by offering a contract they knew would be bad at the end but very cap efficient for the prime of their core
in the next few years, they would also lose, for cap reasons:
Versteeg
Ladd
Buff
etc
etc
So Chicago is a very good example of what happens to good teams in a cap era, even though they did plan for the long term, they knew that some of these contracts would be bad at the end but they wanted a long window of being good and they were willing to accept the position they're in now if it meant winning cups. It worked
Also, did they make any older player additions like Keith would be now? I don't remember any. I think Chicago did the opposite of what you think they did