It feels like we've wondered about Zdeno Chara's impending retirement for the past five years. A one-year extension back in March put a stop to that, at least temporarily.
When Chara's current deal runs out, he'll be 43. Eventually, it's going to come to an end, right? After sustaining an ankle injury against Carolina in the Eastern Conference final and breaking his jaw while blocking a shot against St. Louis in the Stanley Cup final, it was like watching a mummy trying to piece his game together - he held his own given the excruciating pain, though.
The hulking 6-foot-9 blueliner has made a career out of being one of the toughest defensemen to play against. But how much more does Chara have left in the tank? He's starting to get too slow for today's NHL and he doesn't use his blistering slapshot nearly as much as he used to. Boston has good defensive depth and Torey Krug is more than capable of running the left side.
Chara, a seven-time NHL all-star and 2009 Norris Trophy winner, won't need to wait long before he's inducted into the Hockey Hall of Fame. And while he says he hopes to play a few more years, does he have it in him to actually do so? That's the thing: we've been asking that for a few years now, and he keeps coming back, and his uncertain status as an upcoming UFA will fuel the discussion once more.
It's early, but who are the other pending UFAs in the twilight of their careers? Taking the age of the player at the start of 2020-21 into account, here are some of the leading candidates to call it a career after this coming season:
Ryan Miller, G (age at start of 2020-21: 40)
Regardless of team, it's hard to argue that Miller doesn't have some of the best style in the league when it comes to goalie equipment. Unfortunately, injury issues have limited Miller's starts over the past few years (most notably, a six-week break due to an MCL sprain last December) and his reliability has been an issue. He was brought in to mentor John Gibson and steal a few wins along the way, but Kevin Boyle impressed enough in a five-game stint last year that he could be called upon in 2020-21. If this is his last season, Miller will retire as the NHL's all-time wins leader among U.S.-born goalies, so it's safe to say he's had a career to remember.
Craig Anderson, G, (age at start of 2020-21: 39)
Anderson has been through it all with Ottawa during his nine years with the club: the spoils of coming so close to a Stanley Cup final appearance to...whatever you would call last season. He's been the team's rock in net for the past decade and has a history of stealing games for the Senators when all else would've failed. But he'll be 39 when 2020-21 comes around and it might just be time for both parties to move on despite Anderson giving the Sens some of the best goaltending the club has ever seen. The only way he may stay is if the Sens don't feel confident in their depth chart to give someone else the reigns right away, but Anders Nilsson is signed until the end of 2020-21 and Marcus Hogberg and Filip Gustavsson will be looking for their big break by then.
Ron Hainsey, D, (age at start of 2020-21: 38)
It's no secret Toronto coach Mike Babcock loved using Hainsey, but cap issues resulted in the defenseman moving on to Ottawa this summer. Hainsey provides a veteran presence to a defense group that will have Christian Wolanin, Thomas Chabot, Christian Jaros and Erik Brannstrom in the mix, all of whom are under the age of 25 and with limited NHL experience. He'll be the hockey dad for Ottawa's future on the blueline, but they'll have a crowded defense group if all goes well this coming season. After a good season as a leader, it'll be time to focus on keeping the blueline up to speed.
Deryk Engelland, D, (age at start of 2020-21: 38)
It was hard not to be happy for Engelland after Vegas picked the hometown defenseman in the 2017 expansion draft. Since then, he has become a leader in the community off the ice and a fan-favorite on the ice. Engelland said he hopes to play a few more years, but Nicolas Hague and Zach Whitecloud, among others, could make him expendable. He seems happy in Vegas and he'd probably retire before he would go somewhere else after living out his one-year, $700,000 deal this season. It's safe to assume he'll be with Vegas in 2020-21, but not as a player.
Jason Spezza, C, (age at start of 2020-21: 38)
One of the best feel-good stories of the summer was seeing Spezza return to his hometown team in Toronto on a one-year deal at a league-minimum $700,000. The Leafs are still Cup contenders, giving him the best chance to win a championship since making the final with Ottawa in 2007. His deal signals that he'll be a depth player and may not dress every night (he was a healthy scratch on occasion in Dallas) but if he can carve out 20-30 points on the fourth line and play on special-team units in the playoffs, he'll bring good value to the Leafs. But he'll be 38 when 2020-21 kicks off and his play has declined enough over the past few seasons (from 50 points in 2016-17 to 53 in the past two years combined) that he won't have much left to give. Expect this to be his swan song, but a popular one for fans and Spezza's family alike.
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