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Sports fans love to reminisce over the days where it all went wrong: the wasted draft pick, the tragic trade or the defecting hero. These may not be, by definition, the worst roster moves ever made, but they were the ones that affected us on a personal level. These are the events that caused -- and still cause -- us to sit on our bar stools and lament the cruel twists of life.
|CNNSI.com wants you to send us your memories of the day your heart was broken by a team, player or GM.
React to any of the deals listed here.
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Then keep your eyes open for when we run your reactions on CNNSI.com.
Bruins fans flooded CNNSI.com with their tales of woe, starting, of course, with the stunning departures of idols Bobby Orr and Ray Bourque 24 years apart; followed by the Phil Esposito trade; the premature retirement of Cam Neely; the 1972 trade of Reggie Leach; and the failed homecoming of Kevin Stevens.
| June 24
| D Bobby Orr signs free-agent contract with Chicago
For 22 years, Bruins fans struggled to comprehend how Bobby Orr's career came to such a depressing end in a Blackhawks uniform. Then, in 1998, the world (Orr included) learned that Alan Eagleson, Orr's agent and the head of the Players' Association, had withheld details of a contract offer that would have kept Orr in Boston for the remainder of his playing career by making him a minority owner in the club.
Tony Triolo/Sports Illustrated
The reported 18.5-percent ownership would have amounted to about $20-40 million today. Instead, Orr walked out on the Bruins and to this day has never had any official involvement with the team for which he revolutionized the role of defenseman. Eagleson, who bilked Orr out of most of whatever money he did make, served time in Canada for his role in elaborate, illegal schemes that skimmed money from the players he represented.
In his 10 years with the Bruins, Orr won every major award at least twice (except the Calder, which he only won once, duh) and won two Stanley Cups. He was the face of the Bruins and of the NHL, the Gretzky of his time. He led the league in assists five times and in overall points twice ... unheard of for a defenseman at the time. For him to leave was absolutely devastating to Bruins fans, who no doubt consider his departure the biggest disappointment in team history. The Bruins haven't won a Cup since.
As for Orr, he played only 20 games for the Blackhawks in 1976-77 before knee surgery virtually ended his career. He returned in 1978-79, but lasted only six games before retiring. He lives in Boston and still is an ambassador of sorts for the Bruins, but he has never fully reconciled his differences with the team and has never held a formal position.
|| Rich Lundin, Worcester, Mass.
"It was the most awkward thing to watch. First the news conference -- Bobby crying. Then watching him in red and black instead of black and gold. Then later finding out that his agent never told him that the Bruins offered him a stake in the team! That's how I found out that as you grow up, sports turn from a love of the game into a business."
Three years after Orr left Boston, young Ray Bourque showed up and immediately filled the seemingly unfillable void. Starting with a Calder Trophy in 1980, Bourque put in 21 full seasons with Boston, winning the Norris Trophy five times and earning 18 All-Star bids.
And 24 years after losing Orr, the Bruins lost Bourque.
| March 6
| Boston trades D Ray Bourque and
LW Dave Andreychuk to Colorado for
F Brian Rolston, Martin Grenier, Sami Pahlsson and a 1st-round pick (Martin Samuelsson)
The comparisons are unavoidable: stalwart defensemen, trophies on the mantel, perennial All-Stars, good community men. But the ways and means by which Orr and Bourque left were quite different.
Ray Bourque left Boston as the all-time goals leader for defensemen. Brian Babineau/Allsport
Orr left bitterly over money, an issue that never came up between Bourque and management. In fact, Bourque had often drawn the ire of the NHLPA for his willingness to re-sign with Boston with minimal negotiations over the years. Several times, he could have been the watermark for defenseman salaries, but instead he would usually quietly and quickly agree to terms.
No, Bourque left apprehensively for a ring. And as disappointing as it was, many Bruins fans didn't blame him. The Bruins' thrifty spending and hard line stances with their own players gave even Bourque's closest advisors reasons to say, 'If you want the ring, make the move.'
|| It's A-OK to root for Ray
Boston Herald -- March 7, 2000
By Steve Buckley
Perhaps the easiest way to explain the greatness of Raymond Bourque would be to give you the numbers - that he logged 21 seasons with the Boston Bruins, that he's scored 395 goals, that he's won five Norris Trophies, that he's an 18-time NHL All-Star, that he represented his beloved Canada in the Olympics.
Put aside the numbers, though, and this is the easiest way to explain the greatness of Raymond Bourque: In 21 seasons as a Bruin, he never disgraced his uniform, his teammates or his adopted city. With Bourque, it was quite the opposite.
He would show up, night after night, season after season, and deliver the goods - solid performance on the ice, solid performance off the ice. Always. He was as much a gentleman as any athlete who ever graced the Boston sports scene, a man loved by the fans, the media, his teammates and every one of the coaches, front-office executives and scouts who have worked for the Bruins.
Raymond Bourque gave back to Boston far, far more than he took. He is one of the few athletes whose mere presence made Boston a better city than when he arrived. In an age in which we throw up our hands and concede that athletes should not be role models for kids, Raymond Bourque was and always will be a terrific role model. You can point to him on the ice and say: "That's the way the game should be played." You can point to him off the ice and say the same thing.
|| Sean Edmunds, Franklin, Mass.
"Whether you were happy he was getting a better shot at the Cup in Colorado, or you were crushed because you wanted him to finish his career in Beantown, it was a dark day. I couldn't watch Bruins games for a couple weeks after that. But now the fans of New England have two teams to root for in the Stanley Cup playoffs. I wish Ray all the best of luck and continued success."
|| Scott Leger, Fairlee, Vt.
"This cut the remaining ties to my childhood and many others ... 19 years and never a bad thing said about him or from him. Just worked hard. Knowingly or not, he was a role model for all the blue collar workers in the area. Bruins vs Avs for the Cup? Go Avs! I watched Raymond more than all the current Bruins combined."
This was a wash. An aging Espo never quite rose to the occasion in New York, and Park and Ratelle lost their star appeal in Boston. It was a case of both franchises underestimating the value of identity.
| November 7
| Boston trades C Phil Esposito and D Carol Vadnais to the N.Y. Rangers for D Brad Park, C Jean Ratelle and D Joe Zanussi
It was very nearly impossible to tell whose fans were more outraged.
Neil Leifer, Melchior DiGiacomo/SI
Traded to Boston from Chicago in 1967, Esposito became the NHL's first 100-point scorer and led the league in scoring five times. Planting his big body in front of the goal, he scored a then-record 76 goals in 1970-71. Boston bumper stickers read: Jesus saves ... and Espo puts in the rebound.
Esposito's whole identity was with the Bruins, and many Rangers fans could not warm up to him. His production was steady (34, 38 and 42 goals in his first three full seasons in N.Y.) but not even close to his numbers in Boston. Midway through the 1980-81 season, Espo lost interest and hung up the skates ... though he remained in the Rangers organization and eventually became the GM.
|| "When the Buzzer Sounds"
Triumph Books ; 2000
By Charles Wilkins, Colleen Howe and Gordie Howe
He could [score] so well, in fact, that he had every reason to believe he'd be a Bruin forever. The story is told that when got the news of his trade he sat on the bed in a Vancouver hotel room and wept. "If you tell me I'm traded to New York," he told his coach, Don Cherry, "I'll jump out that window."
According to Phil, it took him two years following the trade to accept that he was no longer a Bruin. "I'd look in the mirror with the New York sweater on, and I'd say, 'Hey wait a minute - where's the Boston crest?' "
|| Stewart Dean, Woodstock, Ontario
"A trade of former superstars that were the heart and soul of both teams and were never fully appreciated in their new surroundings as aging veterans."
| September 5,
| RW Cam Neely announces his retirement
Profile of a city: Ray Bourque and Cam Neely in 1991. Damian Strohmeyer/Allsport
Cam Neely was the embodiment of the power forward. Actually, he might have been the first to be called that. Always crashing the corners, always crashing the net, his fearless, kamikaze style of play endearing him to fans from Southie to Hah-vahd Yahd.
"It was fun to know you had Cam on your side," Ray Bourque once said.
Of course, fearless kamikaze style of play comes with a price. For years, Neely had battled injuries -- to his thigh, his knee and finally his hip -- always coming back to be a good player. Many think the injuries were all related: the treatment for the thigh injury damaging his knee, and his hip being affected as compensated for the leg woes.
Of course, many others point a finger at Ulf Samuelsson, who leveled Neely with a vicious hit in the 1991 playoffs. Neely went after Samuelsson later in the game and the two collided hard again. In the weeks that followed, a brick-sized bony tumor grew in Neely's left thigh. Then came knee problems, then his right hip began to turn arthritic.
He played just 22 games over the next two seasons, scoring 20 goals and 10 assists. Then he blew everybody away by scoring 50 goals in just 49 games in the 1993-94 season. He lasted two more seasons, scoring as long as he could get on the ice.
But his body just broke down too quickly and his career came to a premature end. Neely tried a comeback, but found he just didn't have the strength.
|| It's unique loss for Sinden, Boston
The Boston Globe -- September 6, 1996
By Bob Ryan
Cam Neely was - is - huge. When Neely was popping in 50 goals a year, he was a monster sports figure in this town, and if the team had won a Stanley Cup, he would practically have been off the scale. I mean, come on. What didn't Neely have?
Talent? He invented a new position you, [GM] Harry [Sinden], coined yourself. In your perennially eclectic sports mode, you decided that Neely was hockey's answer to a power forward in basketball.
Charisma? You kidding? Guys lugging six beers at once down the Garden aisle loved him because he whacked people. Hockey coach types who loved the purity of the game idolized him because he had a surgeon's touch around the net. The press gave him an A-plus because he was always civil and decent. And you want to talk about cross-gender appeal? News of his engagement set off suicide watches among the adolescent female population of this here town. Cam Neely had something for everybody.
He is only 31, and now it is over. You look at him standing there and you say it can't be, but it is. His right hip says N-O, no. When Neely couldn't race his 10-year-old brother-in-law from the front of a New York movie theater to the corner without severe pain, he knew he was kidding himself. There was not going to be any more hockey for him.
You never know when a prospect is going to bloom, but when a kid scores 261 goals in 189 goals for the Flin Flon Bombers, you gotta believe he can do something right.
| February 23,
| Boston trades RW Reggie Leach, D Rick Smith
and D Bob Stewart to the California Golden Seals for D Carol Vadnais and D Don O'Donoghue
But after Reggie Leach, aka "The Riverton Rifle," scored only 9 goals in his first 79 NHL games, the Bruins tried to cut their losses by trading him. They netted an All-Star defenseman in Carol Vadnais, but also had to watch Leach grow into his nickname.
After two-plus seasons in California, Leach was traded to Philadelphia, where he scored 45 goals and won a Stanley Cup in 1975. The next season, he scores 61 goals in the regular season and 19 more in the playoffs, where he almost single-handedly eliminates Boston by scoring a record five goals in the clinching Game 5. The Flyers are swept by Montreal in the finals, but Leach wins the Conn Smythe Trophy.
He would remain one of the league's most consistent scorers for the next seasons, including another 50-goal year in 1979-80.
Nothing sells in Boston like a hometown kid. So even though it cost two talented young forwards, many felt the price was right to land the first American 50-goal scorer who just happened to be from Brockton, Mass., and played at Boston College.
| August 2,
| Boston acquires LW Kevin Stevens
and RW Shawn McEachern from Pittsburgh
for RW Glen Murray, RW Bryan Smolinski
and a 3rd-round pick (Boyd Kane)
Sports Illustrated called the deal "a steal" for the Bruins. Stevens had scored 54 and 55 goals in winning back-to-back Cups with the Penguins in 1991 and 1992. But the next season, with Mario Lemieux on hiatus, Stevens had 15 goals in 27 games.
Kevin Stevens' stay in Boston was all too brief. Rick Stewart/Allsport
He underwent extensive surgery after a face-first fall to the ice, and then showed up in Boston dealing with severe back pain. Bruins coaches and fans also doubted his effort. With 10 goals in 41 games, a bitter Stevens was shipped out to L.A. despite an alleged no-trade promise.
"They're a bunch of liars," Stevens said in The Boston Globe. "Assistant GM Mike O'Connell swore on his kid's head that he wouldn't do it. I wouldn't have come here if I'd known this was going to happen. I gave up a lot of money and a lot of bonuses to come here. It's sick. A lot of people told me that I shouldn't believe anything they tell me. But when someone looks you in the eye and tells you something like O'Connell did, well, I believed him. I asked him what was going to happen if things went bad and he said they wouldn't trade me. He told me not to worry. Pittsburgh didn't even really want to trade me, either, that's the sick thing. That's the hardest thing for me to swallow. If they hadn't promised they wouldn't trade me . . . but they did. That's the thing that stuck in my head. It sucks."
|| Local guy, B's make bad match
Boston Herald -- January 26, 1996
By Steve Buckley
Now, this will not sit well with those of you who adore Stevens. He's a big, studly guy who grew up in the area and played at Boston College, and it didn't hurt any that, unlike just about everybody else connected with the Bruins, he knows what it's like to play on a Stanley Cup champion.
Surely, the Bruins reckoned Stevens would bring some of that winning know-how to the new crib on Causeway Street.
They also thought it cool that Stevens is one of those I-grew-up-watching-Bobby-Orr local boys made good, which is probably why they chose him to model their new uniforms during training camp.
It was just about the only time Stevens was seen wearing both a smile and a Bruins uniform. ...
... Stevens, the local kid who could probably tell you Espo's linemates and Pie's favorite postgame hangout and Billy Spear's uniform number, could not himself become a Big Bad Bruin. He played in 41 games. He collected 10 goals and 13 assists.
What happened? Was it the pressure of playing before the hometown fans? Is Stevens being revisited by some psychological pests from the horrific facial injury he suffered when he was with Pittsburgh?
"These are some of the mysteries of athletics," Sinden said. "Who knows what it was?"
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