How a Steal Became an Abomination for Boston

When Phil Kessel was traded from the Bruins on September 18th, 2009, it marked the end of a bitter contract dispute that dragged on for months. Kessel got the money he wanted, and Boston received Toronto’s 1st round pick in 2010 and 2011, and Toronto’s 2nd round pick in 2010.

How It All Unfolded

In the 2009-10 season, the Maple Leafs finished with the second worst record in the league, and were rewarded the second overall pick. Problem was, that pick belonged to Boston. Immediately, the hockey community laughed at the Leafs and said the trade was bound to be one of the most lopsided in history.

The reason being was that the Bruins now had the opportunity to select Tyler Seguin, who was coming off a 106 point season for the Plymouth Whalers. The Bruins also selected Jared Knight with the Leafs’ 2nd round pick that year.

In 2010-11, Seguin made the Bruins in his first year after being drafted, and while he was not a dominant force, did help the Bruins win their first Stanley Cup since 1972.

Meanwhile, the Leafs continued to struggled again and finished with the 9th worst record in the NHL. Once again, their valuable draft pick belonged to the Bruins. They used it to select Dougie Hamilton, a lanky two-way defenseman from the Niagara Ice Dogs of the OHL.

Dougie Hamilton Flames
Dougie Hamilton (Winslow Townson-USA TODAY Sports)

In 2011-12, Seguin and Hamilton exploded. Seguin scored 67 points in his sophomore campaign, and Hamilton led the OHL in points by defensemen with 72 in just 50 games. The Leafs didn’t make the playoffs. The trade that was already laughable became downright joke.

After a solid, but unspectacular 2012-13 season for Hamilton and Seguin, change was on the way. Seguin was dealt to the Dallas Stars in exchange for Loui Eriksson, Joe Morrow, Reilly Smith, and Matt Fraser.

Seguin’s talent and star potential was clear, but reported off-ice maturity issues led to Boston cutting ties with their budding superstar.

In 2013-14, the pieces that Boston received in exchanged for Seguin failed to live up to expectations. Loui Eriksson was hindered by concussions and scored just 37 points after averaging 69.5 over the previous four full seasons. Reilly Smith, however, was a nice surprise that chipped in 51 points.

Tyler Seguin
Tyler Seguin

Meanwhile, Seguin found his groove in Dallas and ripped off a career year that included 37 goals and 47 assists for 84 points, 4th most in the league.

2014-15 was very similar to the previous year. Seguin continued his scoring tear that saw him register 77 points and finish 2nd in the league in points-per-game. Loui Eriksson improved from his previous year’s point totals by ten points to 47, but Reilly Smith regressed to 40 points.

The one bright spot was the emergence of Dougie Hamilton. He finished the season with 42 points, was the Bruins’ best defenseman on a regular basis, and looked to be the heir apparent to Zdeno Chara that would anchor Boston’s defense for years to come.

It All Came Crashing Down

On Draft Day 2015, the Bruins did the unthinkable and traded Dougie Hamilton, who represented the future of their blue line. In a crunch with the salary cap, the Bruins apparently did not believe they could meet Hamilton’s salary demands.

The return they received was underwhelming to say the least. They received a 1st round pick in 2015, and two 2nd round picks in 2015. Many believed the Bruins could have (and should have) gotten much more in return.

The hilarious cherry on top? Minutes after announcing the Hamilton trade, the Bruins signed Adam McQuaid to a 4-year, $11M contract.

What’s Left of the Kessel Trade?

All three of the original pieces from the Phil Kessel trade (Tyler Seguin, Dougie Hamilton and Jared Knight) are all gone from Boston. The trade that was lauded as highway robbery by the Bruins has turned into a joke on them, as they traded away two franchise players. What they got in return is far worse than what they gave up.

Here is a breakdown of the assets the Bruins have left in their organization that stemmed from the original trade:

Loui Eriksson: a two-way 2nd line winger whose PPG has been on a steady decline over the past four years

Reilly Smith: a middle six winger

Joseph Morrow: prospect who is a veteran of 15 NHL games, may become a bottom pairing NHL defenseman

Draft Picks #14, 45, and 52 in 2015

Zack Phillips: a prospect with no NHL experience and 59 points in 141 career AHL games