Let me end the suspense right now for you: he's #1 on this list.
With the Bruins having won their first Stanley Cup since 1972, I thought it might be worthwhile to take a look at how we got here. This will be a two part series: first, the 10 worst trades in Bruin history since 1972.
I'll give you one guess as to what part 2 of the series will be.
These are trades that didn't make the cut, but are frequently mentioned in the "worst trades" conversation, so at a minimum, I owe you, dear reader, an explanation for why these two big deals missed the top 10:
Glen Murray and Bryan Smolinski for Kevin Stevens and Shawn McEachern.
The Bruins got great value in this deal...just not in the way they thought they did. They thought the value was in Stevens, when in fact Stevens was already washed up, but no one outside Pittsburgh knew it. A combination of drugs and rough and tumble play on the ice (most notably having his face shattered after a hit on Rich Pilon) led to Stevens best years being long behind him. However, McEachern was a real find, and on his own, combined with the fact that Murray only became a real NHL sniper after he returned to Boston later in his career, would have made this deal almost acceptable.
I know what you're saying. "But Phunwin, McEachern only played one year in Boston!" Trust me, we're coming to that.
Adam Oates, Rick Tocchet and Bill Ranford for Jim Carey, Jason Allison, Anson Carter and a 3rd round pick.
I will defend this trade to the death. This is the definitive "Harry Sinden is cheap" argument. To be sure, he shipped out a lot of salary without taking much back. And yes, Oates still had plenty of gas in the tank; traded at the age of 34, he would lead the NHL in assists two more times before retiring. But neither Ranford nor Tocchet had much to contribute; in fact, Ranford was busy posting Vesa Toskala-esque GVT numbers (-11.7 and -14.0 from 1995 through '97). Meanwhile, Allison gave Boston three phenomenal years, and Carter was a quality winger as well, both at low cost. When you can get good production at low cost, you're making out well. It doesn't hurt that Allison was ultimately spun for Murray at the peak of his value, nor that Carter was traded in part for Bill Guerin.
Below the fold, the top (or if you prefer, bottom) 10...
10. 16th pick in the 2003 draft for the 21st pick, 66th and 107th.
The 2003 draft was an absolute goldmine of NHL talent. Maybe the best draft of all time. Sitting at 16, the Bruins had shots at Zach Parise and Ryan Getzlaf...and instead traded down to pick Mark Stuart at 21. This isn't a case of hindsight being 20-20, either; Getzlaf and Parise were picked at 17 and 19. That was like reaching into a bag with two $100 bills and a $1 bill, and getting your hands on George Washington's mug.
Mitigating factor: They got Patrice Bergeron in round 2 of that draft, a choice I'm not convinced they would have made without the extra second round pick. That entire Bruins draft was filled with brutes and bangers; the Bergeron pick almost felt like they were saying "we've got an extra second rounder, let's take a flier on this skill guy from the Q."
I hated this trade at the time. McLaren had pretty much zero hockey IQ (his cheap shot on Richard Zednik turned the series in favor of the Habs), but he was a big, tough defenseman who could skate. He would give the Sharks another 4 years of quality top 4 play, while the Bruins got zilch from Jillson and Hackett. Worse, the fourth round pick turned into Torrey Mitchell, who is emerging as a quality bottom 6 forward.
This one rates as Peter Chiarelli's worst trade, and hopefully it will stay that way. Apart from a brief period of productivity, Bochenski did nothing in Boston and ended up as a journeyman. Versteeg went on to play a huge role for the 2009-10 Cup champions and looks like he'll be an excellent 2nd/3rd line forward for another 8-10 years.
Mitigating factor: Bochenski scored 22 points in 31 games after the trade, while Versteeg was still in the minors, so for a little while, the trade looked good. Alas, that was the high water mark of Bochenski's career.
7. Andy Moog and Gord Murphy for Jon Casey.
This is why you never, ever overreact to a bad playoff loss. Coming off a first round sweep at the hands of the Sabres, culminating in the famous "May Day" goal (you can kiss my ass if you think I'm linking to that damn thing), the Bruins dealt Moog out of frustration. To be fair, Moog was objectively awful in that series, posting a 5.22 GAA, giving way to the immortal John Blue at one point, and looked to be in decline. However, the Bruins turned him into Jon "Technicolor Five Hole" Casey, who gave the Bruins one crummy year before moving on as a free agent. Worse, the Bruins sent Gord Murphy to Dallas for "future considerations", which ended up being the Moog for Casey trade. Murphy wasn't special, but he was a fairly competent defenseman who wouldn't embarrass you in a second or third pair. So, while the trade is remembered as Moog for Casey, it was actually Murphy and Moog for Casey. Moog would have a career renaissance in Dallas, having excellent seasons in 1994-5 and 1996-7.
Mitigating factor: statistically, this made all the sense in the world at the time. Moog's GVT plummeted from 15.7 to 5.6 to 1.2, while Casey, 2 years younger, was coming off a perfectly respectable 8.9. Plus, it did inspire one of Kevin Paul Dupont's best nicknames ever.
6. 1st round pick for Landon Wilson and Anders Myvold.
Somewhere toward the end of his reign, Harry Sinden just decided to stop valuing first round draft picks. (Oh, don't worry, it gets worse.) I don't know why a GM with such a focus on cost control would deliberately deprive himself of the easiest way to repeatedly bring in cheap, young talent, but he did. If you've heard of either of the guys Boston got in this trade, give yourself a pat on the back. Who did that first round pick become? Robyn Regehr. I'm going out on a limb and saying that the Bruins could have used a decade of Regehr's rock-solid defensive play. Hell, it might have even saved them from the boneheaded decision described in #10.
Mitigating factor: Colorado made an even worse trade than this, involving Regehr. They took Regehr in the draft, then shipped him to Calgary with Jarret Stoll, Rene Corbet and Wade Belak for Theoren Fleury and Chris Dingman. Fleury was an Av for about 15 minutes, and then his substance abuse problem started bubbling to the surface.
5. Ray Bourque and Dave Andreychuk for Brian Rolston, Martin Grenier, Sami Pahlsson and a 1st round pick.
Bourque, of course, had another year and a half of all-star level play before going out on top. You knew that. What you might not know is that Andreychuk had 4 more 20 goal seasons in him before retiring. Boston got four pretty good years of Brian Rolston and nothing else. That's a pretty slim return for two Hall of Famers (I assume Andreychuk, he of the 640 career goals, will be in one day). What makes this worse, however, is that Philadelphia was reportedly offering Simon Gagne for Bourque. The Bruins preferred Colorado's package, presumably because Rolston had more NHL experience to his credit.
Mitigating factor: This.
4. 1st round pick, Mariusz Czerkawski and Sean Brown for Bill Ranford.
We're getting into the truly awful deals now. Everything up to this point had at least something resembling a rationale behind it. The Bruins couldn't know that Parise and Getzlaf would be THAT good. The Bourque deal sucked, but they were doing him a favor, etc. This deal, however, was one that made no sense at the time. Czerkawski was an exciting young prospect who was starting to turn into a big time scorer. And for Christ's sake, he was married to a Bond girl. How do you deal a guy like that? Brown was Boston's first round pick from the season before. So, really, they were dealing 2 first rounders and a great young scorer (Czerkawski would go on to score 215 NHL goals, including a 4 season stretch where he had 108), which is a lot, but I could live with it if they were getting a prime goaltender. Here's the problem: they didn't. Rumors were rampant for weeks that the Bruins were going to get Curtis Joseph from Edmonton. Joseph was on the outs with the Oilers, and it was well known that they were going to move him. Yet, when deal time came, it was Ranford, not Joseph, that was headed east. As an added bonus, not only did Boston get a much worse goaltender than they'd been negotiating for, but all the rumors absolutely crushed whatever confidence young Blaine Lacher, who was coming off a sterling rookie season, may have possessed. Ranford was awful in Boston after his acquisition, while Czerkawski and Brown went on to decent NHL careers. And the first round pick? At 19th overall, the Oilers took Matthieu Descoteaux. He did nothing, but two guys picked shortly after that made something of themselves: the 21st pick was Marco Sturm, the 24th was Daniel Briere.
Mitigating factor: they sent Ranford off in the perfectly defensible Allison/Carter deal above, salvaging at least something from this abortion. Plus, the amount of blame one can put on this trade for Lacher's collapse is debatable. It's more likely that the kid caught fire one season, and then everyone just figured him out.
3. Joe Juneau for Al Iafrate.
Ancient by NHL rookie standards, the 25 year old Juneau scored 102 points in his rookie season for the B's, including 70 assists, which remains an NHL record by a left wing. His second season was going much the same way, with 72 points in 63 games, when he was traded to Washington for Iafrate. Iafrate took a polar opposite route to the NHL; while Juneau toiled in college, and was called up largely because of a breakout campaign at the 1992 Olympics, Iafrate was an instant success, making the NHL at 18, and already having 4 all-star games to his credit. He was big, he could skate like the wind, and had a wicked shot. He had 12 points in 13 games and seemed to make the trade justifiable. And then, the injuries happened. Well, they happened again. Iafrate had a medical file thicker than a phone book when he came over in trade. He'd been mostly healthy for the last two years, so the risk seemed minimal. Alas, Iafrate never suited up in Boston again after those 13 games, missing the entire next two seasons to injury, and then retiring from the NHL after a brief period with San Jose. Juneau totaled 572 points over his career, providing quality second/third line play for a decade after the trade.
Mitigating factor: well, at least the Bruins learned that you shouldn't overpay for a puck moving defenseman, right?
2. Shawn McEachern for Trent McCleary and a third round pick.
I remember where I was when I read about this: I was sitting in the computer lab in college, trying my best not to shout a string of four letter words as I read about this trade. The Bruins stumbled onto McEachern mostly as a throw-in to the Stevens deal above. They obviously didn't realize what they had, though, because they turned around and traded him the following offseason. Over his career, McEachern managed 253 goals and 323 assists. McCleary had a rep as a grinder...or at least, I assume he did, because I can't find anything in his minor league numbers that would suggest "hey, this kid's going to be good!" This draft day trade contributed mightily to Boston's dreadful 1996 draft, one that set a new low for incompetence and helped set the stage for the franchise's fall on hard times a few years later. The third round pick, Eric Naud, played not a single NHL game in Boston, but at least he had company; no one else in that draft did either. Who did they pass on? Massachusetts high school product Tom Poti went a few picks later; you'd assume the scouting department had at least a passing familiarity with him. Oh, there was one other guy they passed on, too. You might recognize him.
Mitigating factor: That aforementioned fall upon hard times was what helped Harry Sinden decide to move to the sidelines. Sinden did a tremendous amount for the franchise; you'll notice that there aren't a lot of trades from the 70s and 80s up there. That's not because I'm lazy, it's because Harry Sinden had the magic touch back then. But he was losing that touch by this time, and it showed. Unfortunately, it took another 6 years after Sinden stepped aside before they got a GM who knew what he was doing, but hey, better late than never.
If you don't know why this trade ranks as the worst in the last 39 years of Bruins hockey, we here at Stanley Cup of Chowder would like to welcome you, and we hope you're enjoying your first few days as a Bruins fan. (Please be advised that it's unlikely that every season will end in a Stanley Cup.) Thornton had just been signed to a long term contract extension immediately after the lockout was lifted, and then traded 3 months later in a deal that didn't even rate as a "three quarters for a dollar" type deal. It was more like a dime and two pieces of pocket lint for a dollar.
On a personal note, this trade, coming as it did immediately after a one year lockout, led to me giving up hockey for a couple years. That's right, this trade stunk so badly that I, a Bruin diehard of 20 years, actually threw up my hands and said "forget it. I'm done with this sport and done with that cheapskate Jacobs." It took the Savard/Thomas/Chara trifecta to bring me back.
Mitigating factor: Without this trade, we never would have seen this. Other than that...I got nothing.