Sometimes picks go wrong. It's not like Vaak was a huge reach, he was looking like a fantastic partner long term for McAvoy early on, but unfortunately development is never linear and he fell off. We can look at every draft (as can any team) and find a pick better than who they chose, but seems like a pointless exercise in hindsight, except for maybe the draft who shall not be named.
But thing is, when we've been exercising a bit too much about it, maybe there actually is a problem with it. Especially what they've done with our firsts... really stunted the organizations ability to stay in the elite coming into this decade. I mean what I'm typing isn't anything new, but a recap just to see it all at once:
1 decade of Bruins first rounders and what the Bruins accomplished or did with them. Just covering 1st rounders, as an extensive full draft drill down would be even longer.
2021: Fabian Lysell, a lot of promise and Bruins most exciting prospect in a while. TBD
2020: Did not select, traded with part of Backes contract & prospect, and for a handful of games of Kase. (Anaheim selected Jacob Perreault)
2019: John Beecher, promising player, MAYBE middle 6 upside, TBD? Bruins lose in SCF.
2018: Did not select, traded to NYR with part of Belesky's contract, Lindgren & Spooner for... Rick Nash and a quick playoff exit. NYR selected Jacob Bernard-Docker)
2017: Urho Vaakanainen, swing and a miss. At least he was rated somewhere around there. Better players obviously on board. There's still time, but it's probably running out given the Bruins recent defense-core.
2016: McAvoy & Frederick, McAvoy is a cornerstone piece, and Frederick is young and an NHL player... with what looks like limited upside. Frederick pick was from a trade with SJS for long-time Bruin Martin Jones ( /s)
2015: Don't think I even need to say anything here. We all know. For the record, Senyshyn was the Flames pick acquired for Hamilton, Zboril was the pick acquired from LA for Milan Lucic, and Debrusk was the Bruin's own pick.
2014: Chiarelli still, but Pastrnak seems like the last top 6 forward we've been able to draft and develop ourselves in the past decade.
2013: Did not select, but we had a cup appearance and added a Jersey collection for any Jagr fans out there. (Dallas used pick to select Jason Dickinson). Bruins lose in SCF.
2012: Malcom Subban, waived and lost for nothing (later traded for Robin Lehner).
2011: TOR pick, Dougie Hamilton, moved for picks, which ended up being Zach Senyshyn, Jakob Forsbakka Karlsson, and Jeremy Lauzon (recently selected via expansion draft). Boston pick traded to Ducks via Toronto (Rickard Rackell). Bruins win Stanley Cup.
So a DECADE of 1st round picks accomplishments and where it brings us today:
Accomplishments: 1 Stanley Cup , 2 Stanley Finals losses, 3-5 opening night starting lineup players
Current players:
2014 - Pastrnak - Top line RW, NHL star
2015 - Zach Senyshyn - fringe NHL/AHL tweener
2015 - Jake Debrusk - Struggling middle 6/bottom 6 forward
2015 - Jacob Zboril - current depth defenseman, unable to hold a steady job in the lineup
2016 - McAvoy - Top pairing RHD
2016 - Frederick - Current depth, 4th line winger
2017 - Urho Vaakanainen - AHL call up-7/8th defenseman
2019 - John Beecher - TBD
2021 - Fabian Lysell - TBD, recently signed
How this affects our current roster?
Forwards (3 top 12 fowards)
xxx - xxx - Pastrnak
xxx - xxx - xxx
Debrusk - xxx - xxx
Frederic - xxx - xxx
xxx
Senyshyn
Defenseman (1 top 6 defenseman)
xxx - Charlie McAvoy
xxx - xxx
xxx- xxx
Zboril
Vaakanainen
Goalies (this position was mostly unaffected, besides the blunder of wasting a pick to select Malcom Subban)
xxx
xxx
So maybe this is a POINTLESS exercise, but maybe a lesson in how we've managed our assets in the last decade and how we can actually improve from past mistakes. I know every single player and pick won't play on this team, but we've also done an awful job at using any of those trades to find lasting core players on this roster. Zboril and Frederic are the best players we've acquired from picks we traded for (which says a lot), and we used 1/5 of the last 10 years of our own firsts to get rid of bad contracts. We've managed to use none of those firsts to bring back players that actually played on the team more than a full season (not counting Kase as he literally managed to play 9 regular season games and 11 post-season games as a Boston Bruin), I understand that's the cost of being a contending team, but we really could have done better than getting rid of bad contracts or buying rentals.
tl;dr: While it's a pointless exercise to go back and see what they could have done, it's an opportunity to learn from mistakes and hopefully do better drafting, developing, and/or trading.