The Boston Bruins have had their fair share of controversial decisions over the last couple of decades. It started with the Joe Thornton trade, and continued when they shipped young stars Tyler Seguin and Dougie Hamilton out of town in the early 2010s. It seemed like the Bruins were building a dynasty, and Seguin practically fell into their laps at the 2010 draft thanks to a first-round pick from the Toronto Maple Leafs.
Seguin made the team in his first year with the team, and had some bright moments. The Bruins were a deep team during the 2011 playoffs, which led to Seguin being a healthy scratch at times, but he had some clutch goals during that run and still has the Stanley Cup ring to prove it. It seemed like he was a massive part of the future, but the front office had some other plans.
Seguin was part of the 2013 team that returned to the Stanley Cup Final, but they failed to finish the job which led to the front office trading him to the Dallas Stars shortly after the start of free agency. Seguin had just one goal in 22 games during that run, and adding in past incidents where he overslept for meetings and other behavioural concerns, the front office decided it was time to cut bait.
It turns out that the decision might've been a wake-up call, as he had 84 points in 80 games with the Dallas Stars the following season and has been a valuable player for them ever since, while also wearing a letter as part of the team's leadership group. The easy criticism for the Bruins is that they gave up on him too early, grabbing poor value for a 21-year-old who was three years removed from being the second-overall pick.
Loui Eriksson had 147 points over three seasons with the Bruins, while Reilly Smith had 91 over two seasons. Joe Morrow played just 65 games, and Matt Fraser played 38. It wasn't even close to the value that Seguin could've given them, and there's no telling how different the team would've been through the late 2010s with another offensive piece like Seguin added to those successful rosters.
Seguin could even be a massive help now as the Bruins search for more offensive depth in the top six. While some moves like the Joe Thornton and Dougie Hamilton trades helped the Bruins get to where they were going (the Hamilton trade was good for it's value, but it was the draft picks they accrued from the deal that flopped), the Seguin deal put them five steps backward. It's scary to think how good the Bruins could've been if they had just given Seguin another season or two to prove his worth. It isn't like they received massive value from the Stars for his services.