The problem with the "hindsight is 20/20" line is at the time it wasn't. There was TONS of pushback on their picks AT THE TIME. Zboril & JDB weren't sexy but defensible. The top 75% of 1st round-rated players are generally safe consensus NHL regulars with varying opinions after that. But Senyshyn was wildly off the radar. Rated as a 3rd rounder & a project. Mid-1st round project picks are not defensible. It was a horrible pick then and an even worse pick now. There were slam dunk picks just sitting there. Why do you think people never stop complaining about it? Because it was a horrible pick. ZS is a bust for where he was picked. 100%. Maybe he'll stick in the league in a bottom 6 role. But there was 0% reason to pick him where they did with lots of picks later. And we are seeing the effects now.
People forget that Zboril over Chabot wasn't really controversial at the time. That was just an error in the Bruins scouting. In multiple rankings Zboril was above Chabot, and their average rankings were pretty close. In fact, looking back at some of the Saint John Sea Dogs threads, most of the fans preferred Zboril and thought he was a safer pick. IIRC, Zboril was viewed as the safer and better all around pick, whereas Chabot had a higher ceiling but was hit or miss.
DeBrusk was ranked in the mid-high 20's on nearly every list, so that was still a reach by Sweeney and the scouts. Although technically a "hit", the consensus was that Connor/Barzal/Konecny were superior players at the time, and they have all proven to be superior players 5 years later. 14 was too early to pick DeBrusk, as he was not the best player available. He was picked about 6-10 spots too early. If we had the 20th pick and selected him, that would've been fine. The Senyshyn pick was an absolute disaster. The consensus on Senyshyn was that he was a mid 2nd round pick.
Had the Bruins just selected Barzal, Connor and Zboril, the franchise would be in a much different position right now, and the window would be open for a longer period of time. The future would look a lot brighter. Connor, Barzal and (insert player here) would be the best 2nd line in the NHL, and take the pressure off of the 1st line. The RW, whoever that would be, would flourish with those 2 elite players. It would cause teams to adjust their game plan, as opposed to only trying to shut down one line. Depending on if they would've traded Krejci during the 2018 offseason, Coyle would still be the 3rd line center. Krejci would've fetched a top 6 forward (to complete the 2nd line) or a top 2-3 D that we need. The team also could've kept Krejci through this year, until Barzal's ELC was up, and been working the phones to deal him for a top 6 forward or top 2-3 D. Additionally, Kyle Connor would still be on his ELC as well. WPG burned one year of his ELC in 16-17 after an injury.
IMO, with Barzal and Connor, we would've won the cup last year. Think about what our top 3 playoff lines would've been last year:
Marchand-Bergeron-Pastrnak
Connor-Barzal-(Top 6 RW Sweeney would've traded for)
Johansson-Coyle/Krejci-Heinen