The price of success, no? I mean, the players he re-signed who were part of back-to-back Cups would have been re-signed by pretty much any NHL GM. I personally do not like the Hornqvist contract because of his likely imminent decline, but Dumoulin is fine, Rust is OK, even Maatta would not be too bad if he had maintained greater health.
As for those he has brought in since, the Johnson deal is the one everybody cannot stand. The cap hit is not terrible, imo, it's just the term. But there are far worse contracts out there, and far worse defensemen too. Just saying.
Gudbranson? Bjugstad? McCann? None of those deals are a problem for me. JR continues to tinker to find the right mix because his head coach cannot seem to be satisfied with anything he does. The coach does not even like most of the players JR brings in...i.e. Reaves, Brassard, Pearson.
Our issue is coaching more than personnel. Stanley Cup winners are being chastised and one will almost surely be shown the door. I still have a problem that it has come to this re: Kessel. The man is clutch. He was the best player in the postseason in 2016, but thanks to the rep he has had to carry since the Toronto media absolutely destroyed him, he did not win the Conn Smythe. But make no mistake, when we trade Phil Kessel this off-season we are trading away a Conn Smythe winner. Mike Sullivan does not like him. Boo frickin'hoo.
Last point: JR wins the vast majority of the trades he makes. But when the coach depreciates his assets, it is kinda hard to keep a perfect record on that front.