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Mookie Betts. Tom Brady. Rob Gronkowski. Torey Krug. And now, Zdeno Chara

On Wednesday, Chara joined the parade of longtime Boston sports stars to leave town in 2020. The now-former Bruins captain signed a one-year deal with the Washington Capitals worth approximately $795,000.

As the NHL approaches its January 13th start date, the veteran defenseman lingered on the list of unsigned players and remained hopeful that he would be able to stay with the Bruins for another season. Ultimately, the team elected to not bring back their captain for a 15th season, forcing Chara to find another team.

"Recently, The Boston Bruins have informed me that they plan to move forward with their many younger and talented players and I respect their decision," Chara wrote in a farewell Instagram post on Wednesday. "Unfortunately, my time as the proud Captain of the Bruins has come to an end."  

Although he's heading into his age 44 season and is not nearly the player he once was, Chara is still a serviceable depth defenseman on a good team, plus a respected and beloved presence in the locker room. For the Capitals, it's a deal that makes a whole lot of sense -- especially at a minimum price tag.

But it's also a deal that would have made quite a bit of sense for the Bruins, who have taken a curious approach to this offseason. Boston had a few glaring needs after being eliminated at the hands of the Lightning in last year's playoffs: Secondary scoring/forward depth and security on the blue line. 

To this point, the most notable moves of the Bruins' offseason have been the addition of Craig Smith (a nice depth piece) and the departures of Krug and Chara. Not exactly the step forward needed to keep their Stanley Cup window open.

By letting Krug and Chara walk, Boston is banking on some younger, unproven players being able to carry the weight -- especially on the left side of the defense. They'll likely have some combination of Matt Grzelcyk (who re-signed earlier this year), Jeremy Lauzon, Urho Vaakanainen, Jakub Zboril and John Moore on the left side heading into this season. Of that group, Grzelcyk is arguably the only player that has earned a significant promotion on a contending team.

Perhaps getting younger and taking a chance on these guys is a plan that will pay great dividends. At the very least, it allows the team to gauge what they've got. But this is a team that won the Presidents' Trophy last year and is two years removed from reaching Game 7 of the Stanley Cup Final. This seemed like an offseason for aggressiveness -- an opportunity for the team to add final pieces to try to capitalize on the current core's closing window. Instead, a few key core pieces have departed, only to be filled by uncertainties. 

It seems like the approach of a team looking to transition into a new era rather than sell out and maximize the current one. Is it the right choice? That's up for debate, but the following is not: This approach by Bruins' president Cam Neely and general manager Don Sweeney will undoubtedly open the front office to intense criticism and scrutiny heading into this season. 

Not only is management banking on unproven pieces capitalizing on the opportunities given to them, they're also essentially banking on Chara not being worth a minimum salary cap hit. And a 44-year-old Chara playing in a condensed, meat-grinder schedule this NHL season? Maybe it's a fair bet. 

But it's unwise to doubt Zdeno Chara's physical limitations and contributions as a depth defenseman, even in his elder years. It's also unfair to overlook what he's meant to the Bruins for the last decade and a half. Since coming to Boston in 2006, Chara has established himself as one of the best and most influential Bruins of this generation. Without Chara and the culture he established as captain, there's a good chance the Bruins don't see the organizational renaissance that they've experienced since his signing. That Stanley Cup in 2011? Hard to see it happening without Chara.

Ask any current or former Bruin their thoughts on Chara and what he's meant to the team on and off the ice over the years. You'd have a difficult time arriving at a single negative sentiment. He was beloved in the locker room and he'll remain beloved in Boston's locker room even as he finishes his career in Washington. 

By electing to part ways with a guy like that -- a pillar of the organization -- a front office is opening itself up to a lot of heat. Scores of Bruins fans are already furious that the spoked B won't be the final uniform that Chara wears. They'll be even more furious if the plan in Boston, as murky as it may be, doesn't pan out. They'll also probably be furious if Chara excels in Washington. 

Of course, business decisions are a difficult part of sports. In shoving Chara out the door, the Bruins made the difficult business decision to move on from a legend in order to push the organization in a different direction. It's part of the job of a front office to separate emotions from the day-to-day and not get too attached to any certain player, so maybe Boston's front office deserves a bit of credit for sticking to their convictions about the state of the roster.

But in this particular case, it's hard to shake the feeling that the Bruins are not only overlooking the stability that Chara could provide for next year's team (on and off the ice) but also failing to appreciate what he's already done for the organization. If things don't go the way Boston is hoping in 2021, it's a legacy move that could stain this management group for a long time.