By Michael Hurley, CBS Boston

BOSTON (CBS) — As we all try to figure out what exactly the Bruins’ long-term plans and organizational philosophy might be, a report out of Canada suggests the team’s most recent strategy has been one born out of buyer’s remorse.

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In Elliotte Friedman’s “30 Thoughts” column for SportsNet, he explored the current chatter surrounding the Boston Bruins. Friedman said that Joe Haggerty’s report about a potential offer sheet for restricted free agent Jacob Trouba could help explain exactly what the Bruins were looking for when they were trying to trade down in last weekend’s draft.

They ultimately failed in that endeavor and decided to select Trent Frederic at No. 29 overall, a spot much higher than any scout anticipated. Even the Bruins themselves stated that they don’t see a top-six forward in Frederic, making the selection at No. 29 all the more puzzling. (They couldn’t have taken him with their second-round pick at No. 44, because they traded that away for Brett Connolly a year earlier, and they apparently feared Frederic might be off the board by the time they picked again at No. 49, a pick acquired in the Johnny Boychuk trade.)

But Friedman has presented some potential clarity on just how specific their trade requests may have been that night.

From Friedman:

The Jacob Trouba offer sheet story from CSNNE’s Joe Haggerty fills in some blanks, including: why was Boston trying to move down in the draft on Friday night? The obvious answer is the Bruins knew they could have selected Trent Frederic lower than 29th, and wanted to get extra assets while still landing their man. However, the offer-sheet possibility reveals another motive: to try and regain their 2017 second-rounder (now owned by New Jersey for Lee Stempniak) or 2017 third-rounder (to Philadelphia for Zac Rinaldo). Any offer sheet with an average annual value between $3,755,233 to $9,388,080 involves one or both of those selections. The picks offered as compensation must be your original choices — you can’t acquire someone else’s selection and offer it up instead. So, if you don’t have yours, you must get it back.

Friedman’s as plugged in as anybody in the NHL, and he’s cautious to not publicize rumors unless he’s got good reason to believe they’re likely to be true.

So, if we assume for a moment that this suggestion is true — that the Bruins were asking for their picks back from the Devils and Flyers — then we must pass a message along to Bruins general manager Don Sweeney. And it’s a message from an old woman in an insurance commercial.

This is, of course, the National Hockey League. It is the highest level of hockey in the world. Certainly, for any executive, mistakes are going to be made. But never does a GM or team president get the chance for a complete do-over within a year of the initial blunder.

That’s not how this works.

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Obviously, when this chart was tweeted this week and showed just how limited the Bruins’ options were in terms of restricted free agency, the picture was grisly. Due to their lack of second- and third-round picks, the Bruins were handcuffed, only capable of making a measly offer on a bad player or making an exorbitant offer on a good player — and at the high cost of paying four first-round picks.

For any non-playoff team looking to rebuild on the fly, this is a most troubling scenario. But that does not mean that the team has a chance to hit the easy button and erase very bad deals from the past.

As a reference point, everyone in the world knew the Rinaldo trade was horrific as soon as it happened. Rinaldo has roughly the same number of suspensions from professional hockey as he does NHL goals. A player like that can be acquired for nothing. Instead the Bruins relinquished a real live asset in order to acquire his services. He rewarded them for that show of good faith by tallying three total points and earning a prototypically Rinaldonian suspension in early March. He followed it up by earning an AHL suspension a few days later.

To say it was poor asset management would be an insult to the words “poor,” “asset” and “management.” It was simply a disaster.

The Stempniak trade may place less blame at the feet of Sweeney and more on ownership and/or Cam Neely. It’s hard to know exactly which minds in the organization felt the team was good enough to not only make the playoffs but to make a decent postseason run that could justify surrendering more assets. But whether it was Neely, or Sweeney, or either of the Jacobses who decided to put a foot to the gas pedal, the end result was the dumping of a prospect, third- and fourth-round picks in 2016, and second- and fifth-round picks in 2017 for Stempniak and John-Michael Liles.

As was noted extensively at the time of the trade, the Bruins could have had Stempniak all along for nothing but money — the veteran’s minimum in fact — because Stempniak participated in Bruins captain’s practices prior to last season. So, giving up a second-round pick and a fourth-round pick for him a few months later was yet another example of poor planning and poor asset management.

The Bruins only ended up getting a grand total of three goals and seven assists from Stempniak in 19 games before failing to reach the playoffs, rendering those two picks wasted. Additionally, the decision to retain Loui Eriksson instead of trading him for prospects and picks showed just how much the Bruins believed in their existing roster’s ability to compete.

Now, just a few months later, the Bruins apparently wanted those exact picks back, and they probably wish they picked up a few extra picks by trading Eriksson. And because the other GMs don’t exist to provide charity to Don Sweeney, the Bruins didn’t get what they wanted.

Learning on the job as a first-time GM can be difficult, and Sweeney’s now been offered his most dense educational lessons on draft night for two straight years. Last year, he learned teams may not be eager to help out if you have a glut of mid-first-round picks. This year, he learned teams again won’t be interested in helping him make up for a past mistake.

Those mistakes have now been mounting for over a year, and with no easy way out, the real impact of those errors may truly manifest themselves on the ice this season in Boston.

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You can email Michael Hurley or find him on Twitter @michaelFhurley.