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Don Sweeney is having his Peter Chiarelli moment.

The current Boston Bruins General Manager is at a crossroads similar in nature to that of his predecessor in Chiarelli– except this time it’s forward thinking.

No, not that forward thinking.

Sweeney’s masterplan has made up for Chiarelli’s deficits in both defense and cap management. Yet, for a team that’s tied with the Nashville Predators for allowing the fewest goals against (88), its offense is nothing spectacular– ranking 25th in goals for so far this season (94).

Through 34 games, the Bruins are 4th in the Atlantic Division with a 18-12-4 record and 40 points on the season despite numerous injuries.

At one point in time this season, five of Boston’s regular six defenders were injured.

In Chiarelli’s final years with the Bruins, defense became a problem. 

The 2013-14 President’s Trophy winning Bruins team amassed 117 points on the season with a plus-84 goal differential. The 2014-15 Bruins missed the postseason and had 93 points on the season and a plus-10 goal differential.

The franchise’s second ever President’s Trophy winning roster had Johnny Boychuk in his prime to rely on. The 2014-15 team did not, thanks to a trade made by Chiarelli prior to the start of the season.

Boychuk was traded out of salary cap constraints that could have been avoided had Chiarelli a) moved other assets or b) not signed those other assets to such inflated extensions in the first place.

Chiarelli promised he’d find a fix for the opening he created, but that never came to fruition as he was later fired in the 2015 offseason.

Upon Sweeney’s hiring, it was clear the Bruins needed a revival on the blue line.

In addition to that, Sweeney was walking into an organization that was needing to negotiate with then pending-RFA Dougie Hamilton.

Hamilton was coming off his entry-level contract and emerging as a prominent two-way defender with the offensive likes of Torey Krug, in addition to that of a more traditionally framed defender.

When Hamilton wanted out of Boston, Sweeney was looked at poorly for trading the RFA defender to the Calgary Flames in the midst of a foundation collapse in defense.

The problem was that the problem didn’t start then.

It worsened as a result of Chiarelli’s dealing of Boychuk, while Dennis Seidenberg got older and more susceptible to injury without anything in the pipeline to act as an adhesive bandage in a worst case scenario (Sweeney would later use a buyout on Seidenberg’s contract on June 30, 2016).

Sweeney’s Hamilton trade was meant to address the long-term scope, as Zach Senyshyn, Jakob Forsbacka Karlsson and Jeremy Lauzon were all selected with the 1st and 2nd round picks in the 2015 Draft the Flames gave the Bruins in return for adding Hamilton.

Though Forsbacka Karlsson has only emerged as far as the third line center in Boston for now, his chemistry alongside Ryan Donato and Danton Heinen is to be lauded with pleasure as those three forwards remain central to the core in a not-so-distant post-Patrice Bergeron era (Forsbacka Karlsson may end up centering the first or second line someday).

Senyshyn’s been seasoning in Providence as Sweeney brought in the Washington Capitals’ approach to “over-cooking” their prospects in the AHL before calling them up for a seamless transition to the NHL (though, in fairness, it remains to be seen where Senyshyn fits into the long-term plan, if he even makes it).

And Lauzon is near the top of the depth chart in defensive prospects within the organization alongside Urho Vaakanainen and Connor Clifton– if not number one.

Though the blue line is not of concern for Boston, when healthy, the depth of the team in the top-six forwards, as well as run-of-the-mill finds to play on the fourth line has come into question.

Sweeney must take an action to address the need for a winger to play alongside David Krejci and Jake DeBrusk on the second line– something Sweeney aimed to bring in since he began his tenure with the Bruins as General Manager.

Again, scoring fell from the 2013-14 dominant team to Chiarelli’s missteps in 2014-15, so Sweeney dealt a struggling Milan Lucic to the Los Angeles Kings at the 2015 Draft for a 1st round pick (Jakub Zboril), Colin Miller and Martin Jones.

Jones was flipped later that summer to the San Jose Sharks for a 2016 1st round pick (Trent Frederic) and Sean Kuraly. More recently, Miller was claimed by the Vegas Golden Knights at the 2017 Expansion Draft.

In the aftermath of the Lucic trade– and with a spot on the second line to fill– Sweeney signed 2015 Stanley Cup Playoffs star, Matt Beleskey to a five-year deal worth $3.800 million per season.

Beleskey set career-highs in assists (22) and points (37) in 80 games played in his first season in Boston (2015-16), then injuries cut his sophomore season with the Bruins to just eight points in 49 games.

In 2016-17, Beleskey had yet to score a point in 14 games with the B’s prior to being assigned to the Providence Bruins (AHL). He was added as an afterthought turned salary cap balancing equation in the Rick Nash trade last season with the New York Rangers.

When Beleskey’s first season with Boston didn’t yield as much of a breakout as Sweeney expected, he signed David Backes to a five-year, $6.000 million AAV contract on July 1, 2016, expecting the forward to shift from center to right wing alongside Krejci.

In his first season with Boston, Backes had 17 goals and 21 assists (38 points) in 74 games played. He followed that up with 33 points (14 goals, 19 assists) last season in 57 games while battling injury.

Though he has been plagued by injury the last two seasons, Backes  (3-5–8 totals in 29 games) has been relegated to the fourth line when DeBrusk is in the lineup.

Sweeney’s plan to let the kids takeover led to exceeded expectations last season, but with that comes an even higher benchmark for success set for this season. Anything less is a disappointment.

Add to that the expectation for a Cup in three years time from when Sweeney was hired. At least, that’s what Boston’s internal operations was calculating when the front office sat down with Sweeney to interview for his current job.

For a GM that was active in his first month on the job and laid out a plan to take the organization up to where it is now– what’s next?

Sweeney’s not in the hot seat from the standpoint about imminent job security, but rather, he’s being put to the test.

This season, of all seasons, matters that much more.

His track record at the trade deadline hasn’t had any staying power, save for an extra year of John-Michael Liles as a depth defender for 2016-17.

He doesn’t have to hit it out of the park with a trade if he truly believes in the youth movement, which is why the Bruins probably aren’t going to be in the market for acquiring the services of Artemi Panarin.

Then again, if DeBrusk is going to be out long term and head coach Bruce Cassidy can’t split up Donato, Forsbacka Karlsson and Heinen, then it’s going to be worth acquiring a top-six forward that’s a legitimate top-six forward.

Adding Jeff Carter from the Los Angeles Kings would be like adding Rick Nash last season, except for the fact that the 33-year-old Carter is signed through the 2021-22 season at about $5.273 million per season.

If you even want to have a chance to potentially sit down with a guy like Panarin or pending-UFA Jeff Skinner in July, you can’t afford to chip away at your available spending money.

Unless Krejci or Backes is involved, that is.

Even still, Carter’s not set on playing anywhere outside of Los Angeles and might retire if he’s shipped elsewhere. Besides that,  he only has six goals and nine assists (15 points) in 35 games this season.

The only other recent rumors swirling around have been tied to Minnesota Wild forward– and Weymouth, Massachusetts native– Charlie Coyle and New York Rangers forward– and Boston native– Kevin Hayes.

Both Coyle and Hayes are 26-years-old with Coyle having a cap hit of $3.200 million through 2019-20 and Hayes as a pending-UFA this offseason at $5.175 million.

Minnesota’s in the hunt for a wild card spot currently in the Western Conference and sits 17th in the league table. The Rangers are fifth in the Metropolitan Division, 21st in the league standings and falling.

Coyle has five goals and 10 assists (15 points) in 33 games. Though he has the same offensive production as Carter has with the Kings, Coyle is younger and in the midst of his prime, leaving room for potential– especially should he be placed on a line with Krejci and DeBrusk.

But Coyle (6-foot-3, 220 pounds) has only surpassed the 20-goal plateau once in his career (21 goals in 82 games, 2015-16).

Hayes has 9-18–27 totals in 33 games with New York so far this season. At 6-foot-5, 216 pounds, he’s had the hotter hands of the three potential trade targets.

He’s also only reached the 20-goal plateau once in his career (25 goals in 76 games last season), but never had a season below 36 points.

Both the Wild and the Rangers will have enough cap room at the deadline should Boston look to flip a player like Backes to fit either player comfortably on their payroll and still have something to give pending-RFAs Charlie McAvoy, Brandon Carlo, Forsbacka Karlsson, Donato and Heinen in the offseason.

(Regardless, if there’s a team willing to take on Backes’ $6.000 million cap hit now as opposed to flipping him to the Arizona Coyotes later…)

Plus there’s the odd hold-out that the Bruins find themselves in conversation with one of the offseason’s biggest prizes like how they were finalists in the John Tavares arms race last summer.

Sweeney has a plethora of prospects to wager if– and only if– he can lop off one of the larger contracts on his books and land a legitimate top-six forward.

Can he do what Chiarelli failed to do in his final year with Boston and deliver on an as of yet unfulfilled promise?

Come to think of it, if he does acquire a top-six forward that can play with Krejci and leads to a Cup, then he does have a lot more in common with Chiarelli.

It’d just be more like when Chiarelli traded Dennis Wideman to the Florida Panthers in June 2010 for Nathan Horton and Gregory Campbell.