Puck Daddy's Summer of Disappointment: Boston Bruins Edition

(Ed. Note: There’s entirely too much sunshine in the summer. So your friends at Puck Daddy are offering a month of thrown shade and perpetual gloom. Behold, our Summer of Disappointment series, in which we ask fans of all 30 teams to recall the biggest bummer moments, teams and players in franchise history! Please wade into their misery like a freezing resort pool, and add your own choices in the comments!)

Written by Marshall from Days of Y'Orr

Most Disappointing Team: 2009-2010 Boston Bruins

If the night truly is darkest before the dawn, then the end of the 2009-10 Bruins season was darker than the bottomless bags of chocolate donuts than Milan Lucic scarfs down as part of his off-season conditioning program.

Going into the Playoffs, nobody expected the sixth-seed Bruins to make much noise. But then they “upset” the Sabres, while the other top two seeds fell. Suddenly they had home ice in the second round against the Flyers, whom they promptly assaulted so hard there was an episode of Law & Order: SVU based on it.

A 3-0 series lead? Not even a team with Steve Begin and Matt Hunwick could drop four straight against a Michael Leighton-backstopped Flyers team. Right?

A 3-0 game 7 lead? In the first period? Gone faster than Brad Marchand’s shirt on a Tuesday.

Do you know how embarrassing it is to have your team mentioned in the same fleeting breath as David Carradine when it comes to the all time biggest chokers? We’re all just grateful that this year the Sharks grabbed that torch harder than Claude Giroux grabs uniformed butt cheeks.

Most Disappointing Bruin: Zach Hamill

Four career NHL points. That’s fewer than the number of times Adam McQuaid has put himself on the IR packing his luggage.

Looking at a draft in hindsight is a terrible thing to do. I mean, how many teams passed on Patrice Bergeron twice? But looking at all the names that were drafted after the Bruins used the 8th overall pick on Hamill makes you wonder exactly how much cheap Canadian whisky Peter Chiarelli slammed down that day. At least if he had been on a Derek Sanderson style bender he could say he thought he was just drafting Anze Kopitar’s ugly brother.

Side note: It’s spelled “whiskey”. Get your crap together, Canada, Scotland and apparently also Japan.

Logan Couture, Ryan McDonough, Kevin Shattenkirk, Max Pacioretty. All selected within 15 picks after Hamill, whose crowning NHL achievement came in the form of being traded for the Puck Daddy “Most Disappointing Shot of a Legendary Career”: Chris Bourque. Which segues nicely into...

Most Disappointing Moment in Bruins History: Ray Bourque Winning the Stanley Cup with Colorado

Imagine you and your spouse spent 21 beautiful years together. It wasn’t easy, but it was worth it. You suffered the lows and enjoyed the highs together. But there was always something missing.

Those were 21 hard years of trying to conceive and failing. One year after the cumulative heartbreak ends the marriage, you have to see your ex and his new spouse welcome a beautiful little boy named Stanley into the world. And every year, come April, you have to watch it again and again.

Most Disappointing Bruins Transaction: Trading Joe Thornton to San Jose

There have been some abysmal transactions in Bruins history. Somehow, giving Chris Kelly $3 million a year and a No-Trade Clause doesn’t even crack the Top 5. The jury is still out on last summer’s blockbuster between the Bruins and Stars. So for the time being, the title of worst trade in history could only go to former Bruins GM Mike O’Connell, who sent Joe Thornton - his captain and best player - away for an In-N-Out giftcard and a bag of moldy French Crullers. Real recipe for success there.

Marco Sturm, Brad Stuart, and Wayne Primeau. That was what the Bruins got in return for that season’s Ross and Hart Trophy winner. That trade was so lopsided it got mistaken for Tara Reid. Primeau and Stuart were gone after the following season, while Sturm ended up having a respectable five years in Boston. But comparing Marco Sturm to the career Jumbo Joe has had in San Jose is like trying to convince yourself that you really enjoyed George Clooney as Batman. You can make the argument all you want, but you’d just be lying to yourself.

The only redeeming quality of that trade is that this GIF is not in black and gold:

Most Disappointing Bruins Coach/Executive: Jeremy Jacobs

Remember those 2 lockouts in 8 years? You’re welcome, rest of the league. But you guys have only had to deal with the real life inspiration for Scrooge McDuck for a small fraction of time. For as long as any of us have been alive, Jacobs has been the only owner we’ve ever known.

Almost every penny spent attending a Bruins game (about 10,000 pennies for the worst seats in the house) goes right into his swimming pool of gold coins and not to improving any of his products. Keep that in mind when Jordan Caron is seeing huge minutes on the powerplay this year.

At least Jacobs wouldn’t be so cheap as to make the cup sizes smaller every year…

Or give you a half empty pizza box...

The man refused to spend money improving his team for over 30 years, keeping players like Cam Neely from ever winning the Stanley Cup. And then when Neely took over the front office and helped build the team into a winner, JJ had the balls to drop this quote about Neely at his own victory parade:

“...On top of it, he brought us a Stanley Cup, something he couldn’t do while he was skating.”

(╯°□°）╯︵ ┻━┻

Most Disappointing Bruins Fashion Choice: Eliminating the Late 90's Alternate Jersey

If you date a supermodel for a decade, you put a ring on it, not toss her to the curb like Tyler Seguin’s love-stained futon. Therein lies the story of the Bruins 96-06 third jersey, affectionately known as the Pooh Bear. For 10 glorious years, that majestic ursine smile was so contagious you had to wonder if its fur was concealing open sores.

Were our teams pretty awful during that stretch? You bet. But those bright yellow threads were a giant ray of sunshine that wrapped you up like a warm embrace that said “It’ll be alright.”

Miss the playoffs for the first time in three decades?

Trade away your longest tenured captain only to see him win a Cup with Colorado?

But then they took our smiles away. Worst decision ever.

BRING IT BACK! #TeamPooh for life!

They’re not ugly.

Shut up.

You’re ugly.

•  •  •

Other disappointments (in order of appearance): New York Rangers • Calgary Flames • St. Louis Blues • New York Islanders • Dallas Stars • Colorado Avalanche • Washington Capitals • Ottawa Senators • Arizona Coyotes • Minnesota Wild • Edmonton Oilers • San Jose Sharks • Winnipeg Jets • New Jersey Devils • Los Angeles Kings • Florida Panthers • Carolina Hurricanes • Buffalo Sabres • Montreal Canadiens • Tampa Bay Lightning • Chicago Blackhawks • Columbus Blue Jackets • Nashville Predators • Detroit Red Wings • Anaheim Ducks • Philadelphia Flyers • Pittsburgh Penguins • Vancouver Canucks • Toronto Maple Leafs