It's hard to start asking hypothetical questions about Boston Bruins history and not come back to the 2015 draft. It has been talked about in nauseum over the years, and the selections Don Sweeney and the front office make only continue to get worse as players picked later in the first round thrive. It was bad enough when Jake DeBrusk was the only one of the three players picked left in the black and gold, but now that he is gone, we've officially reached rock bottom.
The Bruins shipped off some fan favorites in Milan Lucic and Dougie Hamilton to get draft capital in an attempt to get younger at every position. The plan worked masterfully for Sweeney, as he landed back-to-back-to-back picks in the middle of the first round. It would've been hard for that front office to mess it up, as you'd think they'd be able to hit on at least two of the three selections.
It's hard to look at the selections as a complete failure. DeBrusk has had some big-time moments for the Bruins over the years, some of which have elevated them to playoff series wins and regular-season success. It was the one aspect of the first round where Sweeney made a good decision, but it still doesn't detract from the fact that four players drafted after him have more points and have become key pieces for their respective teams.
The Bruins took Jakub Zboril, Debrusk, and Zach Senyshyn with their three picks. If you're asking where two of those three players are now, it'd be a valid question, and it's an even worse question when you realize some of the names that went after them in the draft. For starters, the next three taken at 16, 17, and 18, were Mathew Barzal, Kyle Connor, and Thomas Chabot.
Maybe Bruins fans are happy with their defense and wouldn't want a player like Chabot, who is a bit on the soft side and does have some injury concerns. Well, there were some other forwards they could've taken, such as Joel Eriksson Ek, Brock Boeser, and Travis Konecny.
The Bruins have a considerable talent issue in the top six of their forward group. There's no guarantee that all the players could've stayed around, but that group would be looking much better with some combination of Barzal, Connor, Eriksson Ek, Boeser, or Konecny.
The bottom six is a bright spot for this upcoming season, while the top lags behind. Imagine a world where the Bruins figured out a way to have the bottom six while also having David Pastrnak and three of the forwards mentioned above to fill out the lineup. All of a sudden, the Bruins go from a potential lottery team to the cream of the crop in the East.
If you're looking at it on a broader scale, the Bruins probably finish the job in 2019 if they had made three better decisions at the 2015 draft. They also probably smashed the regular season points record well before they did it in 2022-23.
The unfortunate truth is, the Bruins had a great two decades for fans to enjoy, but they could've been one of the dynasties that people talk about forever if Sweeney and co. hadn't completely bundled the selection process.