Button fired two coaches, Don Hay and Greg Gilbert, during his three-season tenure (2000-03) as the general manager in Calgary. Neither decision came easy. Both were made after he and his management associates took long and in-depth looks at what wasn't working and why.
"It just comes down to a case of, 'OK, we've reached the point of no return,'" Button told NHL.com Monday. "That is exactly what happens."
McPhee and Rutherford each reached that point of no return over the weekend, and both made decisions Monday morning that rocked the hockey world. McPhee brought in ex-Capitals captain Dale Hunter to replace Bruce Boudreau and Rutherford fired Paul Maurice and hired Kirk Muller.
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Button said a manager rarely knows when the perfect time is to make a coaching change, but the decision typically comes naturally due to the unavoidable signs that go beyond winning and losing.
"We measure things by wins and losses, which you have to, but there's a lot going on behind the scenes," Button said. "There are a lot of things going on behind the scenes that people don't know about -- how you're managing your team, how you're managing internal battles, how you're managing situations not only on the ice, but off the ice."
In Button's case, he said there were specific, internal reasons why he fired Hay and replaced him with Gilbert 68 games into the 2000-01 season, but didn't want to shed light on them publicly other than to say there were conflicts that weren't dealt with the way Button would have liked.
Mostly, though, Button felt he had to fire Hay because he could see that the coach wasn't getting the most out of the team's best players. Button also said he senses that the same problem cost Boudreau and Maurice their jobs Monday.
"I really liked Donnie, and I'll tell you this -- Donnie, technically, from a coaching perspective, is as good as anybody I have ever been around," Button said. "But as time went on, he wouldn't push the best players. I'm not talking about hammering them; I'm talking about pushing them. Pushing them to be better, pushing them so they will be better and our team will be better.
"It shows up and manifests itself in wins and losses, but there's so much that goes to pushing your best players. Scotty Bowman, Ken Hitchcock or whoever you want to talk about, they push their best players. Danny Bylsma pushes his best players."
Button's second coaching change came 25 games into the 2002-03 season when he fired Gilbert and eventually replaced him with Darryl Sutter, who came on board following an 11-game interim stint by Al MacNeil.
The Flames were 6-13-3-3 when Button fired Gilbert. It was a disappointing start on many levels, but mostly because Button felt he made the necessary moves -- adding Chris Drury, Stephane Yelle and Martin Gelinas to a core that included Jarome Iginla, Craig Conroy, Toni Lydman and Robyn Regehr -- to turn Calgary into a contender.
Remember, McPhee and Rutherford also made moves over the summer aimed at raising the bar for their teams, but neither team has come close close to meeting their respective expectations.
"Our team was clearly better than it was performing," Button said of the Flames in 2002-03. "We were losing leads, we weren't able to close out games, and I just felt the essence of a good team is one that understands where they're at in a game and they don't beat themselves. I really thought our team was much better than it was performing. When Darryl Sutter got there, it confirmed it."
Rutherford and McPhee will have to wait to see if they'll get the same type of confirmation. For now, they have to trust that their instincts were right, and Button said that can be as difficult for a GM as it is to come to the conclusion that change is needed.
"The decision to make the change from the exit point of view is one that has been thought about and discussed in depth, but the coach coming in is the key that either validates your decision-making or calls it into question," Button said. "The questions will be numerous if the new coach can't affect positive change because you made the coaching change to do exactly that.
"It'll become, is the team that the GM constructed not good enough? Or does the GM not know what coach is the right fit?"
Follow Dan Rosen on Twitter at: @drosennhl