He got burned by Brian Campbell not re-signing with SJ, then when he traded for Burns he handed out a 5 year contract, followed up by an 8 year contract.
He got burned when PM was the first of the "Big 3" to leave the team, so he signed Vlasic to a massive contract because he wants to keep him.
He got burned when Tavares wouldn't sign in SJ, so he signed Couture to a massive contract, then traded for Karlsson, couldn't lose him after giving up all those pieces so he signed him to a massive contract.
Bits of this are probably correct, but overall not it. He signed Vlasic to make up for being one of the biggest bargains in the NHL through his 20's. Couture's contract is probably close to adequate value (within a half million probably) but got destroyed with the cap not rising. Karlsson was maybe a million over what I wanted at the time but that was the cost of not going to UFA and letting other teams take their shot at him. He just has played like absolute garbage this year.
Guess it goes back to you'll almost never regret the guy you didn't sign to a big deal, but you will almost always regret the guy you did. That said, until there is a leaguewide change in philosophy on those deals, you're almost always going to have to play that game in UFA or trades. Unless you tank for a prolonged period of time to build a Crosby/Malkin, McDavid/Draisatl, Toews/Kane, etc. duo that allow you to just nibble around the edges with ELC guys and cheap short term veteran players you're going to have a bulk of your core overpaid for term because it's better for a team trying to contend to have that guy than to not (same deal with the NFL and QBs).
Really the only solution given where we are now is to get creative and make a big risky trade or to tear it to the studs and accumulate picks for guys that actually have value like Kane, Meier, and Hertl. It would suck in the near term, but that is probably the best path forward given the state of our prospect pool and NHL roster. I like the way that we have drafted the past couple years, but those guys are just going to need time to get here and be good NHL players and this core will be burnt toast by the time that happens. So may as well accumulate more picks to build another core for 2-3 years down the road (barring the miracle DW trade).