The Bruins are hitting the busiest two-week stretch of their offseason. Here are five things to watch. - The Boston Globe (2024)

Sweeney, who will give a state-of-the-team address ahead of the draft Thursday in Vegas, has holes to fill and the cold hard cash to fill them.

Sweeney has some internal items to check off his to-do list, including what to do with his goalies and what becomes of pending free agent Jake DeBrusk.

In Sweeney’s perfect world, he would kept his elite tandem of Ullmark and Jeremy Swayman between the pipes for another campaign as well as keeping DeBrusk in the fold.

Here’s a look at how things could play out over the next fortnight or so.

▪ Net results

Swayman is in line for a massive new deal (at least $8 million per) after proving during the playoffs he can handle the load of a true No. 1. Both sides would love to avoid an arbitration replay, so getting a deal done makes good sense.

Rumors swirled shortly after his All-Star Game selection that Swayman and the Boston brass were closing in on an extension, but it never materialized.

Moving his good buddy Ullmark (who was on the books for one more year at $5 million) should help offset Swayman’s bump in pay.

Ullmark, just a year removed from his Vezina Trophy-winning season, was the most attractive goalie on the market. The 30-year-old has a limited no-trade clause and approved the trade, unlike at the last deadline.

▪ DeBrusk dilemma

Both the club and the winger have a number in mind. Will either (or both) budge?

DeBrusk, 27, will have suitors — the Toronto Star recently reported the Maple Leafs have interest — and he likely will make a decision on his future at or near the opening bell July 1.

Injuries played a role in a down season for the speedy DeBrusk (19 goals, 40 points), but the 2015 first-rounder’s postseason surge (11 points in 13 games) makes him an enticing player.

▪ Internal affairs

Among Sweeney’s top offseason acquisitions last year was Danton Heinen, who went from a professional tryout contract to prime-time cog. The versatile veteran is a responsible two-way player who slotted in multiple spots in the lineup and was one of the club’s top penalty killers. Locking the 28-year-old up to an affordable multiyear deal would make a lot of sense.

Another pending free agent, defenseman Derek Forbort, could be in line for a new deal. Already a popular player throughout the organization, the rugged Forbort further endeared himself to teammates by battling back from a pair of late-season surgeries to rejoin the club for the playoffs. The 32-year-old would provide valuable depth and veteran guidance to younger blue liners.

Similarly, what happens with Pat Maroon?

He fit in nicely after getting the green light following his rehab from back surgery. He provided the big-brother grit the club lacked (particularly after Milan Lucic’s departure). Maroon, 36, gushed about his brief time in Boston, and both sides expressed interest in running it back, with health being a determining factor.

▪ Draft dodgers

The Bruins have often been players at the trade deadline, and they are paying the piper for their (correct) all-in strategies with a lack of draft picks.

As a result of trades for Tyler Bertuzzi, Hampus Lindholm, and Garnet Hathaway, the Bruins have just three selections this year, and their first comes in the fourth round (No. 122 overall). Their other picks are in the fifth (No. 154) and sixth (No. 186) rounds.

The Bruins could move up via trade, with the Senators a possible intriguing partner; Ottawa has a pair of first-rounders (Nos. 7 and 25). That might be a high price to pay, but franchise goaltenders are hard to find, and if Ottawa could have a contract extension in place for Ullmark, it would make parting with a high pick more palatable.

▪ Kid stuff

It’s rare that players make the jump from development camp to the big club, but slick center Matt Poitras did just that last summer. The then-19-year-old showed glimpses of brilliance during the summer and during the season until shoulder surgery put him on the shelf.

Though he didn’t make the initial roster, Mason Lohrei also similarly impressed last July.

Could another youngster make a breakthrough this season?

The camp roster is not set, but names to keep an eye on include defensem*n Frederic Brunet and Jonathan Myrenberg and a trio of local college forwards: Andre Gasseau (Boston College), Oskar Jellvik (BC), and Dans Locmelis (UMass).

Jim McBride can be reached at james.mcbride@globe.com. Follow him @globejimmcbride.