3 Bruins’ Draft Picks That Didn’t Work Out in Boston

The Boston Bruins were notorious for having a good eye when it came to drafting talented players, especially in the pre-Don Sweeney era. The likes of Patrice Bergeron, David Krejci, and Brad Marchand were all drafted in a short window from 2003 to 2006. The Bruins have had a decent track record at the draft since the turn of the millennium, with 12 of their 20 players in their current starting roster being homegrown players.

However, not all draft picks stay in Boston to play their best hockey. Therefore, this list will be counting three Bruins’ draft picks that never stayed in Boston to play the best hockey of their careers. Here’s a look at what the Bruins’ missed out on.

Phil Kessel

Phil Kessel was drafted by Boston fifth overall in the 2006 NHL Entry Draft. He was picked up early due to a very impressive season for the University of Minnesota prior to the draft, where the sniper netted 18 goals and 51 points in 39 games. The Wisconsin-born forward didn’t do that bad in his rookie season with the Bruins, as he compiled 11 goals and 29 points in 70 games. He continued to have a steady increase in his next two seasons with the Bruins, as he stepped up for 37 points his sophomore season, and 60 points in his third season. After his best season yet, and after he showed signs of improvement, the Bruins still decided to trade him.

Phil Kessel Boston Bruins
Phil Kessel, Boston Bruins (cubesbyamanda / CC BY – https://creativecommons.org/licenses/by/2.0)

The Bruins ended up dealing Kessel, an improving scoring threat at the time, to the Toronto Maple Leafs for two first-round picks and a second-round pick. These picks turned out to be Tyler Seguin, Dougie Hamilton, and Jared Knight respectively. Tyler Seguin and Dougie Hamilton made the trade worth it, however, both elite Bruins’ draftees didn’t play more than three seasons for the Bruins’ before getting dealt to other teams. Regardless of how bad the return was on the trade long term, let’s take a moment to see how well Kessel developed later on in his career.

After being traded to Toronto, Kessel put up four 30-goal seasons and two 80-point seasons in his six campaigns in Toronto. However, his prime was most definitely with the Pittsburgh Penguins. After Toronto dealt the American winger to a stacked Pittsburgh team, Kessel thrived. Kessel won two Stanley Cups with the Penguins, after being an integral part of the team come playoff time with an astonishing 18 goals and 45 points in 49 games during those two back-to-back Stanley Cup runs. He would also hit his career-high in Pittsburgh with 34 goals and 92 points in 82 games during the 2017-18 season. Kessel leaves Bruins’ fans aching as they wonder what kind of aid the sniper would’ve been throughout their various playoff runs during the 2010s.

Tyler Seguin

As mentioned previously in this article, Tyler Seguin seems to be another one that got away from the Bruins. Seguin spent a total of three seasons in Massachusetts. He was shipped out at the young age of 21 to Dallas, along with Rich Peverley and Ryan Button for Loui Eriksson, Reilly Smith, and Matt Fraser. None of the players acquired for the star center stayed with the Bruins long term, which makes matters even worse, before we even look at how well Seguin has developed.

Photo Credit: SlidingSideways/Flickr (CC)

At the time of being traded, Seguin had amassed 56 goals and 121 points in 203 games across three seasons. Those totals weren’t bad at all considering it consisted of a rookie, sophomore, and a shortened season in 2012-13. However, the Bruins decided to cash out early on the young center by shipping him out to Dallas. With Texas to now call home, Seguin fit in perfectly and thrived in Dallas as soon as he arrived. The Brampton-born forward scored 37 goals and 84 points in 80 games for the Stars, making the Bruins regret every ounce of the trade they made. For comparison, the main piece in the trade to go to the Bruins, Loui Eriksson, never hit more than 63 points in his three years with the Bruins.

Seguin has definitely proved the Bruins wrong in trying to cash out too early, with the now 29-year-old having reached 70 points in six of his past seven seasons with Dallas. The Canadian center is nothing short of extraordinary on the ice, warranting his $9.85 million AAV contract. The 29-year-old has consistently put up numbers, and still has prime playing years ahead of him if he stays healthy. Imagining the Bruins’ center core, which is already stacked and impressive enough, and adding Seguin is just scary.

Ken Dryden

A surprising inclusion to most, considering the 6-foot-4 goalie was a one-club man for his career. He was drafted 14th overall by the Bruins in the 1964 NHL draft. That very day, Dryden, along with Alex Campbell, was traded to the Montreal Canadiens for Paul Reid and Guy Allen. Out of the four involved in the trade, Dryden would be the only one to play in the NHL. It is safe to say the Bruins once again let talent slip away for near nothing, considering how good of a goalie Dryden was during his tenure.

Goalie Ken Dryden
The classic photo of Dryden’s famous stance. (Photo by Bruce Bennett Studios/Getty Images)

A bit of a throwback as the last player, this is the most successful player on the list. Dryden is amongst the most notable Montreal Canadiens goalies of all time, alongside George Vezina and Patrick Roy. The Cornell University alum was the main starter between the pipes of the Canadiens for the better part of eight seasons from 1970-1979. The Hamilton-born net-minder was superb during his eight-season career having a record of 257 wins, 57 losses, and 74 ties. Although save percentages weren’t calculated so diligently back in the day, we can still note that he held an approximate .922 SV % during his regular-season career.

Dryden, as stated previously, has the most storied career on this list. Dryden was the goalie during the Habs dynasty years where he and his Canadiens went on to win six Stanley Cups in eight seasons, with a quadruple repeat from 1976 to 1979. The Ontario native has also been awarded the Conn Smythe Trophy and the Calder Memorial Trophy, and the Vezina Trophy five times. There is no denying Dryden is one of the best to ever guard a crease, with him being included on the NHL’s Top 100 players of all-time list. There is no way of knowing what the Bruins could’ve accomplished in the 1970s with this giant between their pipes.

Moving Forward

We all make mistakes, it’s just a part of life. Although trading these players before they could make an impact for the Bruins seems brutal, hindsight is always 20/20. All the Bruins could do now is to simply learn from these mistakes, and make sure that talented players stay within the system as long as possible. Who is your favourite Bruins’ draftee that never quite played his best hockey with the Bruins?


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