During the 2009-10 season, Bruins general manager Peter Chiarelli must have felt like he was out in a sail boat that kept springing leaks. And every time he plugged one, another started spewing water.

The laundry list of injuries over the course of the campaign included Marc Savard three times, Milan Lucic twice, Andrew Ference off and on, Patrice Bergeron, Mark Stuat and Dennis Seidenberg. The Bruins’ organizational depth, which Chiarelli is responsible for was tested, and barely passed its trial by fire.

As inconsistent as the play of his team was, Chiarelli also had his peaks and valleys throughout the summer of ’09, fall and winter. Chiarelli failled to protect himself against injuries by retaining at least one veteran as a seventh or eighth defenseman. He dealt Phil Kessel for what looks like a steal now because Toronto earned Boston the No. 2 pick, but overestimated what his incumbent players could produce to make up for Kessel’s loss.

Chiarelli gave his penalty kill a boost by dealing for Daniel Paille, but hurt his offense and grit by shipping out Chuck Kobasew for pieces that won’t arrive in Boston for years (if ever). Dennis Seidenberg was a great addition at the deadline, but Boston was still thin on the back end because Chiarelli moved out Derek Morris and then didn’t use the left over cap room to add scoring. If that wasn’t completely his decision, that’s unfortunate. However, the blame is all his.

Chiarelli has some difficult maneuvering to do this summer. And he’s counting on a new crop of freshly signed prospects, led by that No. 2 pick and Joe Colborne, to invigorate the organization. While he might be able to conjure up a championship-caliber team out of his moves in the next few years, he didn’t do enough to push a team that was the best in the East in ’08-09 over the hump this season.

Season highlight: When Chiarelli re-signed goaltender Tuukka Rask to a two-year contract extension at a cap hit of just $1.25 million per season, he made sure that an evil future filled with offer-sheet threats, endless bargaining and a potential holdout was avoided. Rask went on to a have a Calder Trophy-worthy season and rewarded the Bruins’ confidence in his first NHL season.

Season low-light: When Chiarelli moved Morris to Phoenix on deadline day, it was expected that he would then use the freed-up money to add much-needed scoring. Seidenberg came in and made Boston better, but they still didn’t have enough threats up front to keep opposing defenses working. Armed with enough cap space to add a Lee Stempniak or Raffi Torres, Chiarelli decided to stand pat.

It’s easy now to look back and see that those two players failed to contribute to their respective teams’ playoff appearances (and look at the way Miro Satan played for Boston in Round 1) and say Chiarelli was right. But at the time, the addition of a player with a scorer’s pedigree could’ve been the spark that would’ve allowed Boston to clinch a postseason berth earlier than the season’s last weekend. Plus, there’s no telling how such a player would’ve responded to playing for the Bruins rather than the team he wound up skating for down the stretch.

Final grade: C-plus
More than anything, Chiarelli built a team that was highly resilient when it came to dealing with injuries but still lacked the type of backbone that could’ve prevented the 3-0 collapse against Philadelphia and any number of the dozen of stinkers Boston produced in the regular season. He under-estimated the value of vocal veterans and failed to make the Bruins a better team this season than they were the year before. And then there’s the Andrew Ference extension, which … well, you’ve read it all before.

The crystal ball says … Chiarelli has Taylor Hall or Tyler Seguin handed to him at the draft, mixes in a couple of veterans and puts a productive team that finishes in the top half of the conference next year on the ice. But the overall makeup of the core of the team — Zdeno Chara, Marc Savard, Patrice Bergeron, Rask — will also be in question until it does something to erase the nightmare of the Flyers series.