Don Sweeney might have inherited a salary cap mess from Peter Chiarelli, but at this point there’s a bigger concern surrounding the Boston Bruins organization: their inability to keep young stars before they hit their primes.

After a career-high 36 goals in the 2008-09 season, Phil Kessel was looking to cash in big after finishing his third and final year on his entry level contract. The Bruins were in salary cap prison at the time and couldn’t afford Kessel’s demands. Eventually, amidst reports on how Kessel didn’t want to be in Boston, Chiarelli dealt him to the Toronto Maple Leafs for two first round picks in the 2010 and 2011 NHL Entry Draft and a second round pick in 2010.

That Kessel trade turned to gold when Chiarelli used those first round picks on Tyler Seguin (second overall in 2010) and Dougie Hamilton (No. 9 in 2011). Having a talented goal scorer and a future stud defenseman is something a team like the Black and Gold should have built around.

But then, on July 4, 2013, Chiarelli dealt one of the two prized selections in Seguin and received Reilly Smith, Loui Eriksson and Matt Fraser in return. Perhaps Chiarelli and the Bruins brass, including Cam Neely, might have felt Seguin’s off-ice issues would be a concern amidst media reports during that time. Either way, the return for Seguin hasn’t brought the best of results.

Perhaps the Seguin and Kessel trades were a trend in which the Bruins didn’t want to risk hurting their locker room chemistry. Or maybe something was fishy with the organization in their handling of younger players from the management to Claude Julien’s reluctance to insert a youth movement into his system.

Well, things got even more fishy before Friday’s first round of the Entry Draft when Sweeney and company announced that they traded Hamilton (a Restricted Free Agent coming off a career-high 32 points in 2014-15) to the Calgary Flames for three picks (one in the first round and two in the second). The Bruins used the Flames’ pick (15th overall) on Zachary Senyshyn of Sault Ste. Marie of the Ontario Hockey League — one of three picks that Sweeney whiffed on according to many pundits given that Matthew Brazal and Kyle Connor were still on the board.

A few days later, Hamilton signed a 6-year contract worth $34 million — an AAV of $5.75 million — with the Flames. The Bruins were rumored to have offered him $5.5 million at 4-5 years.

Notice the trend? Maybe Hamilton didn’t want to be in Boston given the offer or the recent history of the team’s reluctance to play younger players in crucial situations. Maybe, as crazy as this whole smear campaign towards Hamilton sounds, the Boston Herald was on to something when an anonymous GM told Bruins beat writer, Stephen Harris, that the 2011 first round pick was a “loner” in the locker room and an “uppity kid.”

Whatever the situation is, Hamilton’s departure is just another alarming signal of the team’s recent history in similar situations.

Granted, not every young and promising player has had the same fate in the Bruins’ system. From Brad Marchand to Patrice Bergeron to Tuukka Rask, there are examples of younger players (at the time) being successful in the system. Torey Krug has provided an interesting dynamic on the blue-line in his two years in Boston. David Pastrnak and Ryan Spooner showed promise in their first full seasons in Boston.

it also must be noted that without Kessel forcing the Bruins’ hand in the summer of 2009, there would be no discussion of Seguin and Hamilton ever donning the Black and Gold. But with the two key pieces of that infamous trade with the Leafs now out of Boston, the skepticism of these high-end talents leaving for greener pastures before their prime years are concerning on Causeway Street.

In an off-season of confusion, it would seem that those greener pastures and the infamous “Thank You Kessel” chants won’t be coming back to TD Garden any time soon.