from Dave Caldwell at ESPN,
"Whatever term you use -- windows, timing, whatever -- it's impossible not to factor how to ride the momentum of core players rising to their optimal playing years," said Mike Milbury, the former New York Islanders GM who is an NHL analyst for NBC.
"And, on the flip side, it's problematic for managers who must deal with those same players whose 'windows,' or prime years, have passed them by. Take Bill Torrey after the dynasty ended," Milbury said, referring to the Islanders' GM who amassed enough talent to win four consecutive Stanley Cups in the early 1980s. "Did he wait too long to convert the aging players to assets, or was loyalty to their success paramount?"
Before the 2016 NHL trade deadline, Washington Capitals GM Brian MacLellan said he was establishing a "two-year window" for the core of his team to win the Stanley Cup, saying, "We're going for it this year, we're going for it next year, and then after that we're evaluating where we're at."
The Caps won only one playoff series in each of the past two years, although there was an enormous asterisk: They lost in the second round each time to the Pittsburgh Penguins, who went onto win the Stanley Cup both seasons. Washington had the best regular-season record in the league both years, and it lost Game 7 of the 2017 Eastern Conference semifinals to the Penguins 2-0.
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