By Michael Hurley, CBS Boston

BOSTON (CBS) — The moves made by the Boston Bruins on Friday were bad — real bad — and they no doubt made them a worse hockey team.

But in no way was this a change in direction for a team that has done almost nothing to improve itself over the past 16 months.

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Yes, the Bruins won the Stanley Cup in 2011 — an accomplishment that seems more and more miraculous with each year that passes. And yes, the Bruins fought with the Blackhawks to a six-game Stanley Cup Final in 2013. Those teams relied on stellar goaltending, a solid defensive corps and balanced scoring to scrap their way through long postseasons. They were good teams — the key word being “were.”

After that crushing Cup Final defeat, the Bruins entered the short offseason by taking one step forward (signing Jarome Iginla) and one huge step back (trading Tyler Seguin). They ensured some long-term stability by signing Patrice Bergeron and Tuukka Rask to massive deals, but they relied mostly on the returning roster talent (plus Iginla) to compete in 2013-14. And it worked.

The Bruins went 54-19-9 and were the best team in the entire league. Though they couldn’t get past the Canadiens in the second round, the team was still among the best half-dozen or so in hockey. Surely, we all figured, the following season would bring similar success and another chance at a Cup.

Except … that was when the dismantling — and the inability and/or refusal to restock — truly began.

Here is a condensed list of the notable transactions the Bruins have made since the trading deadline of 2014. If you’re a die-hard Bruins fan, you may want to avert your eyes.

March 2014: Acquired Andrej Mezsaros, Corey Potter at trade deadline.

June 2014: Drafted David Pastrnak.

July 2014: Re-signed Jordan Caron as their only offseason move.

July 2014: Let Jarome Iginla depart via free agency, while still being on the hook to pay Iginla $3.75 million in 2014-15.

July 2014: Let Shawn Thornton depart via free agency.

September 2014: Re-signed Torey Krug, Reilly Smith. Both would sign extensions again at the end of the season.

September 2014: Signed David Krejci to contract extension.

October 2014: Traded Johnny Boychuk to Islanders for second-round draft picks and a conditional third.

October 2014: Signed Simon Gagne.

December 2014: Lost Matt Fraser on a waiver claim by the Edmonton Oilers.

March 2015: Lost Craig Cunningham on a waiver claim by Arizona.

March 2015: Acquired Brett Connolly and Max Talbot.

June 2015: Traded RFA Carl Soderberg’s rights for a 2016 sixth-round pick.

June 2015: Traded Dougie Hamilton for a mid-first-round pick and two second-round picks.

June 2015: Traded Milan Lucic for a backup goaltender and defensive prospect, while retaining $2.75 million of the winger’s salary.

June 2015: Signed Adam McQuaid to a four-year, $11 million deal.

That right there looks like a whole lot going out (Boychuk, Hamilton, Lucic, Iginla, Soderberg) and not a whole lot filling in the vacated roster room. (Pastrnak was certainly a great pick, but even the Bruins didn’t expect him to make such an impact at age 18.)

And when zeroing in on the Lucic/Hamilton/McQuaid flurry of moves on Friday, it all looks even worse.

Even if you accept the idea that Hamilton refused to sign with Boston and therefore had to be traded, the return of a mid-first and two seconds is simply not enough for an established NHL D-man with three years of experience under his belt. This is a guy who led Boston D-men in scoring and registered more points than four forwards who played at least 70 games — and that’s with Hamilton playing just 72 games himself.

But, you might figure, at least the Bruins cleared $6 million in moving Lucic, plus whatever money Hamilton would have been making this year, right? Well, Sweeney agreed to pay $2.75 million of Lucic’s contract, and he now also has to pay restricted free agent goaltender Martin Jones, who came to Boston in that trade with L.A. Considering Martin is due a raise from last year’s $550,000, and considering there was absolutely no reason to give McQuaid $2.75 million per year, the cap savings of these moves becomes minimal.

(If another team did end up offering McQuaid a contract worth that much money, then nobody in Boston would begrudge Sweeney for letting him go. As it actually turned out, we now wonder if Sweeney is just Chiarelli 2.0, with McQuaid filling the Chris Kelly role. Could the Bruins have not survived without Adam McQuaid?)

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The bottom line is quite jarring: The Boston Bruins have continued to field a roster that has gotten worse as time has passed, and they’ve done very little to present themselves as trying to improve. Surely, they’re trying (right?) but there’s been almost nothing in terms of results.

The offseason truly begins this week with the start of free agency, but the talent pool is not exactly full of players who can immediately fill voids. And none will come cheap.

And so, the Bruins will enter the 2015-16 season holding on to the hope that Zdeno Chara will be back at full health to start the year and will stay that way all season, through his 39th birthday, despite coming off a knee injury that was never repaired surgically, and despite having logged more than 17,000 minutes on NHL ice. They will hope that Dennis Seidenberg’s miserable season can be blamed entirely on his recovery from a torn knee and is not the mark of a steep descent for a player who will be 34 this summer. They will hope that not only will McQuaid stay healthy for the first time in four years but he will also take giant steps forward in his playing ability at age 29. And they have to hope that their prospects will be able to come up and replace the 41 goals and 130 points that departed in the form of Lucic, Soderberg and Hamilton.

That’s a lot of “hope” for a team that fell out of the top six in goals allowed for the first time in seven years, did not make the playoffs and has thus far done very little to improve their chances of even sniffing the postseason next spring.

It goes without saying, but at a certain point, the Bruins have to reverse the trend of getting worse without reloading. Perhaps that will begin soon in ways those of us on the outside of the Causeway Street meeting rooms can’t foresee. But as of now, we know that the cumulative effect of the past 16 months has the Bruins at the moment looking much more like a bottom-tier Eastern Conference team than the perennial Stanley Cup contender that’s rejuvenated hockey in Boston over the better part of the past decade. So much of what was accomplished from 2007-2014 has seemingly been stripped away player by player — or brick by brick, if you will — to the point where the outlook on the Bruins looks as grim as recent memory can serve.

In many ways, that’s disappointing. But for now, the only question left is simple.

When will this stop?

UPDATE: After the acquisition of Zac Rinaldo, an addendum has been written to this story. Check it out here.

Read more from Michael Hurley by clicking here. You can email him or find him on Twitter @michaelFhurley.

The Zolak & Bertrand Show, with Dan Shaughnessy, questioned whether the local media is already turned on Don Sweeney. Listen below:

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