As the Stanley Cup Final reaches the best of three between the Nashville Predators and Pittsburgh Penguins, the NHL’s off-season is getting closer by the day. With the Expansion Draft (tied in with the NHL Awards) and the Entry Draft a mere two weeks away, rumors and speculation will take center stage in the days leading up to the respective events in Las Vegas and Chicago.

Although they haven’t been a part of any speculations aside from negotiations with David Pastrnak on a new contract and their list of protected players for the Expansion Draft, the Bruins and general manager Don Sweeney have an important off-season ahead of them.

So important, that Sweeney may be willing to trade an asset many teams covet in today’s National Hockey League.

“It’s an effort to try and improve our hockey club,” Sweeney told the press at the NHL Draft Combine in Buffalo last weekend about potentially trading the 18th overall pick. “We have had a number of selections the last couple of years and we feel that they’ll all materialize into very good players for the Boston Bruins and I wouldn’t be doing my job if I didn’t explore what could improve our hockey club now in the shorter term. I owe it to our players and the organization to continue to do that.”

As he enters his third off-season, Sweeney’s personnel decisions have been well documented during his first two years as GM.

The misses are quite glaring. They include trading a third round pick for Zac Rinaldo, signing Matt Beleskey and David Backes to long-term deals in consecutive years on the first day of free agency, and trading Reilly Smith for Jimmy Hayes. Smart money has Beleskey and Hayes going elsewhere to continue their careers in 2017-18 – with one likely being bought out – along with Rinaldo, who spent all year in Providence. Backes has four more years left at $6 million per.

The hits, on the other hand, have come in the form of drafting and developing. Sure, the jury is still out on a few of his selections over the years, like the 2015 first round trio of Jakub Zboril, Zach Senyshyn, along with last year’s 29th overall pick Trent Frederic and second round picks Jeremy Lauzon (2015) and Ryan Lindgren (2016) to name a few. But one has to praise the Bruins GM for the selections of Brandon Carlo and Charlie McAvoy over the last two years and their quick development that led to a solid rookie season for the former and a strong first round performance against the Senators for the latter.

Past history suggests that Sweeney may be better off going up to the podium with a new Adidas Bruins jersey in hand and announcing the 18th selection at the United Center. But the Bruins are also in need of filling a couple of key holes – a left winger to play alongside David Krejci and David Pastrnak on the second line and a top-four left-shot defenseman. Neither spot would likely be filled right away if he keeps the selection.

So which veteran(s) could the Bruins exactly be targeting to fill those aforementioned spots?

At left wing, Sweeney could inquire about Gabriel Landeskog, who was the subject of frequent trade rumors last season, especially in Boston. Obviously, including Carlo, who was on the other end of those rumors, would be a non-starter, but perhaps the Bruins’ first round pick could be enticing for an Avalanche team that is in the rebuilding stage. With prospects like DeBrusk, Anders Bjork and Danton Heinen in the fold, Sweeney might look to his pipeline to fill that spot alongside Krejci and Pastrnak, at least to start the 2017-18 season. And in terms of Landeskog, the Avs captain has a cap hit of $5.5 million per year for the next four seasons, so the Bruins may have to ask Colorado to take on some of his salary during that duration.

Though the Bruins defensive prospects look promising, most, like Lauzon, Zboril, Lindgren and Rob O’Gara, are likely a year or more from competing for a roster spot. That’s where Sweeney could put the 18th pick in play in an attempt to pry away a left shot defenseman like Cam Fowler from Anaheim (who enters the final year of his contract with a $4 million cap hit) or one of the Wild’s trio of defensemen – Jonas Brodin, Marco Scandella and Matt Dumba – that could be left unprotected in the Expansion Draft. Whether or not any of these options are realistic is another story, but those names are a little more enticing compared to the UFA market for blue-liners outside of Kevin Shattenkirk – who the Bruins should avoid come July 1.

Keeping the 18th pick would lead to Sweeney taking the best available player on the board. In recent mock drafts from NHL.com and CSNNE.com, the Bruins have been linked to centers Ryan Pohler (St. Cloud State) and Kole Lind (Kelowna, WHL).

In an important off-season, figuring out what to do with the 18th pick is just one of a few crucial decisions for Sweeney and the Bruins front office.