So the 43-year-old defenseman decided to move on after 14 seasons with the Bruins, turning down their contract offer to play a reduced role this season and agreeing to a one-year, $795,000 contract with the Washington Capitals on Wednesday.
"I just felt that what was presented to me and the conditions that were attached to it, I just felt like I had more to offer," Chara said Thursday. "And I respect their decisions and wish them the best, but I just felt like I could still play regularly and play the games. ...
"I still have gas, lots of gas left, and I still want to go out there and do my thing. That's my motivation to still prove that I can play."
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By joining the Capitals, who won the Stanley Cup in 2018 and have legitimate aspirations to do so again, Chara is embracing a new opportunity entering his 23rd NHL season and following a similar path to his friend Tom Brady. The 43-year-old quarterback left the New England Patriots after 20 NFL seasons and six Super Bowl championships to join the Tampa Bay Buccaneers this season.
"I definitely see a new opportunity, new challenges," said Chara, who confirmed he spoke with Brady about his decision. "But also, very much I'm extremely motivated and I'm looking forward to go out there and play and compete. … I think we all have to compete and play our best, and the most important thing is to win the games as a team. So just that's where I'm at right now.
"It's something I had to try. I didn't want to have any regrets not to try it and not go for it."
Chara, who is in Washington and has begun quarantining and the testing that are part of the NHL COVID-19 protocols, said he is driven to win the Stanley Cup again after reaching the Cup Final three times, winning the championship in 2011. He said he'd love to mirror the success Brady is having with the Buccaneers, who have qualified for the NFL playoffs for the first time since 2007.
Chara is in a good position to do that with the Capitals, who are in win-now mode and hoping to raise the Stanley Cup at least one more time with their aging core, which includes forwards Alex Ovechkin, 35, T.J. Oshie, 34, Nicklas Backstrom, 33, and defenseman John Carlson, who turns 31 on Jan. 10. The memory of Washington winning its first championship is beginning to fade after being eliminated in the Eastern Conference First Round the past two seasons.
"I just want to have a fair chance and compete with the guys for the Stanley Cup," Chara said. "That's something that is the goal, but we want to get there through the right process and through the right way."