By Jack Cinquegrana | Follow me on Twitter! @bruinsjc

Five Boston Bruins had remained in Boston since the 2010-2011 season when the Bruins took home the Stanley Cup. Patrice Bergeron, Zdeno Chara, David Krejci, Brad Marchand, and Tuukka Rask re-signed to stay with this strong group, to bring another Cup home.

That was nine years ago, and these five 30+-year-old veterans are running out of time to make their past re-signings with Boston worth it.

What happened?

In the past nine seasons, the Bruins have made the playoffs in all but two consecutive seasons in 2014-15 and 2015-16. Since winning the Stanley Cup, the Bruins have made it to the Finals twice but have fallen to the Chicago Blackhawks in six games back in 2013 and the St. Louis Blues in 2019.

And since 2011, the Boston Bruins have had to part ways with Dougie Hamilton, Tyler Seguin, Milan Lucic, Johnny Boychuk, and Reilly Smith; all players that would help solve the problems we face today. Free agency and the trade market have been less than impressive for Boston’s management, giving up assets for players like Rick Nash and Marcus Johansson for nothing in return. Not bad players by any means, but the cost of acquiring talent like this and not being able to re-sign these players hurt the team in the long run.

I understand that the Rick Nash situation was out of Boston management’s hands, and I do not resent the situation whatsoever. The point is that management is not willing to add the guys that will push this team over the edge because of their potential contract weight, especially considering the swinging misses and low-ball attempts by Boston to the high-end UFAs this fall’s free agency.

What is the point of David Pastrnak and Charlie McAvoy taking less than market value if the Bruins are not going to sign some more players of their skill level? Is that not what they should expect when taking less?

What do the veterans have left?

Of the five previously mentioned players, three long-time Bruins have deals expiring after this upcoming season. Tuukka Rask and David Krejci have one more year left in the black and gold, while 43-year-old captain Zdeno Chara is currently negotiating a deal for the 2020-21 season.

Patrice Bergeron is 35-years-old and a Boston Bruins for at least two more seasons, and his best buddy and linemate, Brad Marchand, has his contract with Boston expire after the 2024-25 season. These Bruins greats are getting old, and it is time to take a hard look in the mirror on whether or not this Cup window is still cracked.

In free agency, the Bruins fanbase looked for management to go after our most significant need: scoring. With Krug walking, the Bruins need a big-time player, and being that names like Hall and Ekman-Larsson are rumored in the same breath as Boston, the expectation was that the hockey club was going to land a big fish. That expectation fell short when the only considerable “get” for the B’s was Craig Smith, a middle-six winger that brings physicality and produces lots of shots on net.

A good signing, no doubt, but this Cup window looks a little bit smaller. With just above $8 million in cap space remaining and Unrestricted Free Agent Zdeno Chara and Restricted Free Agent Jake DeBrusk still to sign, what kind of player are we looking at being able to add. The answer right now seems to be nobody.

Don Sweeney and the Boston Bruins management group have to look at the roster they have assembled and be honest with themselves. Can this club compete with teams as deep as Tampa Bay, as tough and as physical as Dallas or St. Louis, as able to score as Toronto?

The answer was adding Toffoli or Dadonov, in my opinion. An affordable contract for a player that addresses your scoring needs and not breaking the bank to acquire that player. Hall would have been a roster-altering addition and may have made us contenders again, but the deal may have weighed too heavy on the cap, plus someone having to go out the door to keep him.

When all is said and done.

All Bruins fans can agree that these five players on the back end of their careers have made a significant impact on the organization, that they are all five legends, and will be remembered forever and ever.

I believe that each of these five legendary Bruins has a chance to get their numbers retired, all having been in Boston for so long, and for all of the records they have broken and wins, they earned.