Haggerty: Should the Bruins trade first round picks to win now?  taken at BSJ Headquarters (Bruins)

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The Boston Bruins have plenty of draft picks, eight to be exact, headed into next weekend's 2026 NHL Draft, and must decide whether to part with some of their current and future first round picks to in order to be "aggressive" on the burgeoning trade market.

The Boston Bruins have amassed a treasure trove of draft picks over the next few years, and they continued that trend by trading one of their prospects ahead of next week’s NHL Draft in Buffalo.

It’s been common knowledge for a while now that Boston College forward Andre Gasseau (seventh-round pick in 2021) wasn’t going to sign with the Black and Gold after he was not given a guarantee of playing in the NHL within his entry-level contract. It’s an interesting gamble for a 22-year-old forward prospect who doesn’t project to be much beyond a fourth liner if he fully realizes his potential, but the 6-foot-4, 209-pounder did have a solid career at the Heights with 109 points in 131 career games that could project directly into pro hockey.

Anyway, the B’s this week dealt the rights to Gasseau and a 2026 fourth-round pick (120th overall) to the San Jose Sharks in exchange for a better 2026 fourth-round pick (104th overall) and a 2026 fifth-round pick (157th overall). The deal gives the B’s eight selections in next weekend’s draft, including three picks in the fourth round alone, and paves the way for them to have another productive weekend adding young talent to the Boston organization.  

It very likely will not be the same kind of productive NHL Draft that the B’s enjoyed last season, just based on where they are picking after the Toronto Maple Leafs managed to sink their way into the No. 1 overall pick with top-5 protection after sending a future first-rounder to Boston in the Brandon Carlo deal two years ago.

Cam Neely confirmed a couple of weeks ago that it’s looking like the B’s will get Toronto’s unprotected first-round pick in 2028 to complete that trade, though it won’t become official until the Leafs actually send their 2027 first-round pick to the Philadelphia Flyers to complete a deal with them as well.

The bottom line is that this could have been another bountiful draft where the Bruins were able to collect a top-shelf talent, but there is still plenty of promise with the 23rd overall selection and still plenty for them to prove in terms of making better picks at the end of the first round. And there is also some deep organizational consideration for trading draft pick assets in order to make the current team more competitive and meet the pointed requests of players like David Pastrnak, who is desiring a Stanley Cup-level roster as he celebrated his 30th birthday last month at the zenith of his hockey abilities.

“I applaud David [Pastrnak] in the sense of asking for immediate help. I'd say 10 years ago, when [Pastrnak] was working his way into our lineup, maybe the [Patrice] Bergeron, [and Zdeno] Chara [veteran players] said, ‘How good is this young man?’ We might say the same thing about Fraser Minten and [Marat Khusnutdinov] and James Hagens, so [it’s] going to require some patience,” said Don Sweeney. “We all alluded to that last year, that we needed to get back to [being] a deeper skill-based [team], and adding speed to our club. I love the competitive nature of what that comment represents in terms of him wanting [to win a Cup]. It's a disappointing end to a season where we should have been on the doorstep of going back to a game seven [in the first round against Buffalo], in everybody's mind, if we had taken care of business at home.

“So that's a reactionary comment from a really high-level, competitive star player in the National Hockey League, and he's not wrong in the sense that we would like to accelerate when we can. If that means we use the assets [that we hold] represented in the 2028 draft, or is it one pushed to [2027]? The ping pong balls dictated that it wasn't going to be this year [that the B’s get Toronto’s first-round pick], so we have to have everything in play in terms of how we continue to improve our club, and we have that mindset.”

The Bruins hold their own first-round picks in 2026 and 2027, and it appears that they will have three first-rounders in 2028 with their own pick, Florida’s pick used in the Brad Marchand deal, and Toronto’s pick from the Brandon Carlo trade as well. It remains to be seen how things are going to play out with the Panthers and Leafs organizations over the next few years, but there’s a decent chance that both of those picks could be top 15 picks by that future point.

The question now becomes whether the Bruins should deal future assets to become more competitive in the here and now, or hold onto those first-round picks to

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