The Bruins made headlines last week by trading Tyler Seguin to the Dallas Stars as part of a seven-player deal. The move was unusual, since Seguin is still only three years removed from being the second overall pick in the draft, and is generally considered to be one of the most promising young players in the league. The Bruins had their reasons — the team was reportedly concerned about his off-ice partying and whether he was committed to winning — but they’re still taking a significant risk.

How significant? Let’s just say that NHL history is filled with examples of teams giving up on young players too soon. So many, in fact, that you could probably fill out an entire roster using nothing but future stars that some unfortunate team let slip away. And today, that’s exactly what we’re going to do.

As with any attempt at this sort of undertaking, we’ll need to establish some random and completely arbitrary ground rules:

• We’re looking for young players, so let’s say they have to have been moved before they turned 25. That age cutoff eliminates a few obvious candidates you may be expecting to see, like Joe Thornton, Dominik Hasek, and Phil Esposito.

• These have to be actual players who were traded, not future draft picks that were used on star players. If you’d rather read about teams trading away draft picks who turned out to be Hall of Famers, I’d suggest you try here.

• We’re doing a full roster: four centers, eight wingers, six defensemen, and two goalies. We won’t bother differentiating between left wing and right wing, because I hope to someday join the PHWA.

• While I don’t want to get too deep into defining what it means to give up on a player, we’ll exclude certain unique cases where it was clear that the team had no choice but to trade a guy through no fault of their own. That includes the Nordiques trading Eric Lindros and the Thrashers moving Dany Heatley.

• Yes, I will probably forget a few guys. Yes, you will yell at me about this in the comments. Yes, I will act like this doesn’t bother me even though it totally does, then spend the rest of the day passive-aggressively taking it out on my family.

Everyone got all that? Cool, let’s get started

Center

Marcel Dionne, 23 (Detroit Red Wings)



Dionne was the second overall pick of the 1971 draft and had already put up four strong seasons in Detroit, including a 121-point campaign in 1974-75. But the Red Wings hadn’t made the playoffs during that time (and were in the middle of an 11-year streak during which they didn’t win a single playoff game), and Dionne wanted more money than they were willing to give.

The Kings were willing to pay up for a potential franchise player and struck a deal with Dionne. The league insisted that a trade take place, so Detroit sent their star west for a package of … well, not much. Dionne would go on to play 12 seasons in Los Angeles, recording six 50-goal seasons and winning the Art Ross in 1980 (in a tiebreaker over rookie Wayne Gretzky).

He finished his career with the Rangers, retiring with 731 goals and 1,771 points. He ranks in the top five all-time in both of those categories, and only Gretzky and Mario Lemieux recorded more 100-point seasons. He was inducted into the Hall of Fame in 1992.

In hindsight, maybe the Red Wings should have paid up.

Peter Forsberg, 18 (Philadelphia Flyers)



Forsberg was taken by the Flyers with the sixth overall pick in the 1991 draft (a choice that was criticized at the time as being a reach), and spent the next season in Sweden. During the 1992 offseason he was part of a massive package of players, picks, and cash that the Flyers sent to Quebec for the rights to Lindros.

Lindros started his career with several dominant seasons for the Flyers, but Forsberg arguably emerged as the best player in the deal. He won two Stanley Cups with the Avalanche, and is expected to be a strong Hall of Fame candidate when he becomes eligible next year.

Mats Sundin, 23 (Quebec Nordiques)



Ironically, it was the presence of rookie Forsberg (and some other guy named Joe Sakic) that convinced the Nordiques they could move Sundin for veteran help. They dealt him to Toronto for Wendel Clark in a move intended to add the veteran leadership they felt they needed to become a serious Cup contender.

Sundin played 14 more seasons, finished with 1,349 career points and was inducted into the Hall of Fame in his first year of eligibility. Clark played only one year in Quebec before being traded for Claude Lemieux, who did help the Nordiques win a Cup — after they’d moved to Colorado.

Kris Draper, 22 (Winnipeg Jets)



Draper doesn’t have the offensive numbers of some of the other players we could have gone with, but our team needs somebody to anchor the checking line with Middleton, so he gets the last winger spot.

In three seasons in Winnipeg, Draper had played a grand total of 20 games, recording three points. By that point the Jets were happy to unload him on anyone who’d take his contract, and so they agreed to one of the most famous deals in NHL history: They traded Draper to the Red Wings for a dollar.

That’s it. One dollar.

Draper went on to play 17 years in Detroit, winning four Stanley Cups to go along with a Selke Trophy as best defensive forward.

There’s no word on what the Jets spent the dollar on.

Honorable mentions: Doug Gilmour, Garry Unger, Vincent Damphousse, Rod Brind’Amour, Doug Weight

Wingers

Cam Neely, 21 (Vancouver Canucks)



Neely had been a top-10 pick in the 1983 draft, but hadn’t managed to crack the 40-point mark during his first three seasons in Vancouver. He wasn’t getting along with coach Tom Watt, who didn’t like his defensive game, and his development seemed to have stagnated. So the Canucks traded him to Boston for Barry Pederson, a good young center who was just two years removed from a 116-point season.

The deal backfired almost immediately. Pederson had a pair of reasonably good seasons in Vancouver but was never an elite offensive player again. Meanwhile, Neely quickly became one of the league’s best power forwards, scoring 221 goals in his first five years in Boston. His career was eventually derailed by injuries, but he was dominant enough that he was still inducted into the Hall of Fame in 2005.

By the way, the Canucks also gave up a first-rounder in the deal that ended up being a third overall pick. There’s a reason it’s generally considered one of the worst trades in NHL history.

Brett Hull, 23 (Calgary Flames)



This trade is basically the litmus test for the theory that any deal that results in a Stanley Cup is a good one. The Flames shipped Hull to St. Louis in 1988 as part of a package deal that landed them Rob Ramage and Rick Wamsley, two veterans who helped them win their first (and only) title the next year.

But Hull went on to become arguably the greatest winger of all time, scoring 741 career goals (714 of those after he left Calgary). He won a Hart, two Cups, was a first-team All-Star three straight years, and was a first-ballot Hall of Famer.

Jarome Iginla, 18 (Dallas Stars)



And here’s the historical bookend to the Hull deal. This time it’s the Flames getting the future Hall of Famer, while the other side picks up a key piece for a Cup win. In this case that was Joe Nieuwendyk, who’d play seven years in Dallas and help them win the Cup in 1999.

Meanwhile, Iginla played 16 years in Calgary before departing at this year’s trade deadline. He scored more than 500 goals and is arguably the greatest player in franchise history.

Johnny Bucyk, 22 (Detroit Red Wings)



The 1957 deal that sent Bucyk from Detroit to Boston looked like a good one for the Wings. While he was a well-regarded prospect, Bucyk had managed only 11 goals in his first two NHL seasons. And the Red Wings didn’t exactly give Bucyk away — they dealt him for Terry Sawchuk, a future Hall of Famer who was still in his prime.

But the deal ended up working out pretty well for the Bruins: Bucyk went on to play an astounding 21 years in Boston, scoring 545 goals and 1,339 points. He’s the franchise’s all-team leader in goals, and trails only Ray Bourque in games and points. And while Bucyk’s gaudy numbers are largely the result of longevity, he did peak with a 51-goal, 116-point season in 1971.

By the time he retired in 1978, he was the NHL’s fourth all-time leading scorer. He was inducted into the Hall of Fame in 1981.

Markus Naslund, 22 (Pittsburgh Penguins)



Markus Naslund and Alek Stojanov had both been first-round picks in the 1991 draft. Stojanov was a bruising power forward who had gone seventh overall, while Naslund was a skilled winger who’d gone 16th. Both had been disappointments through the first few years of their pro careers, with Stojanov struggling to crack the Canucks lineup and Naslund showing some flashes during three inconsistent seasons in which he was frequently sent down or scratched.

At the 1996 trade deadline, the Canucks and Penguins decided to exchange headaches, trading the two players in a straight-up deal. Naslund continued to develop slowly in Vancouver before finally finding his game in the 2000-01 season. From there, he became one of the league’s best offensive threats, finishing in the top five in scoring three straight years from 2002-04. He spent eight years as the team captain, and had his number retired by the franchise.

Alek Stojanov scored two goals in Pittsburgh. They were the only two of his NHL career.

Ken Hodge, 22 (Chicago Blackhawks)



Hey look, it’s our old friend Ken Hodge again! Yes, Hodge earns the honor of being the only player to factor prominently on both sides of a deal on this list. Years before the Bruins dealt him to the Rangers for Middleton, they acquired him from the Blackhawks as part of the infamous Esposito heist.

A big 22-year-old who wasn’t viewed as much more than a potential third-line bruiser in Chicago, Hodge quickly developed into an offensive threat in Boston. He scored 40 goals three times and had a pair of 105-point seasons (the first of which briefly established an NHL record for points by a right winger).

Tony Amonte, 23 (New York Rangers)



Here’s another test of our “Cup win = good deal” theory. Amonte was a flashy 23-year-old who’d scored 145 points in his first two years in New York but was struggling through a rough 1993-94 campaign. With the Rangers loading up for a Cup run, they decided to move him to Chicago for a pair of veteran reinforcements.

After scoring 15 goals for the Blackhawks in the lockout-shortened 1995 season, Amonte began a streak of five consecutive 30-goal seasons. He made the All-Star team for five straight years, and was a key part of the Team USA teams that captured gold in the 1996 World Cup and silver at the 2002 Winter Olympics. He retired in 2007 with 900 career points.

As for the Rangers, they did win the Cup in 1994, and their return on the Amonte deal included Stephan Matteau, who scored the memorable double-OT Game 7 goal that won the Eastern Conference final.

Rick Middleton, 22 (New York Rangers)



Middleton was a former first-round pick who’d put in two seasons in New York, never topping 50 points. In the 1976 offseason, the Rangers dealt him to the Bruins in a straight-up deal for veteran Ken Hodge.

Despite being only 32 years old, Hodge was essentially done — he played just one more full season before being demoted to the minor leagues. Middleton played 12 years in Boston, topping the 100-point mark twice and recording almost 900 points as a Bruin. An excellent two-way player, he was named the team’s cocaptain for his last three seasons.

Honorable mentions: Mark Recchi, Pavol Demitra, Patrick Sharp, Todd Bertuzzi

Defensemen

Larry Murphy, 22 (Los Angeles Kings)



Murphy was the fourth overall pick of the 1980 draft and was an impact player immediately, scoring 76 points as a rookie (a record for defensemen). But after two more 60-plus point seasons, the Kings dealt him to the Capitals for Ken Houston and Brian Engblom.

That would be the first of many moves for Murphy over a 21-year career that saw him play for six teams. He retired in 2001 having won four Stanley Cups and playing in 1,615 games, at that time a record for defensemen. He was inducted into the Hall of Fame in 2004, and is currently the fifth-highest scoring defenseman of all time.

Zdeno Chara, 24 (New York Islanders)



Chara was a lumbering project in 2001, blessed with record-breaking size but not considered more than a depth defenseman. So the Islanders dealt him to Ottawa, where he almost immediately developed into one of the best blueliners in the league — a distinction he still holds to this day.

Even worse, the Islanders also gave up the second overall pick in that year’s draft, which everyone knew would be Jason Spezza. It was a draft pick and so Spezza doesn’t qualify for this list, but he should be here in spirit.

And what did Islanders GM Mike Milbury get in return for two future superstars? Alexei Yashin, who played just five years with the Islanders but whose multi-million-dollar buyout is still on their books until 2015.

Chris Pronger, 20 (Hartford Whalers)



Pronger was the second overall pick of the 1993 draft (behind Alexandre “Nobody Remembers no. 2” Daigle). But much like fellow no. 2 pick Seguin, he battled off-ice issues and rumors of immaturity, and lasted just two years in Hartford before being dealt to the Blues.

He’d go on to spend nine years in St. Louis, establishing himself as one of the best players in the league and winning both the Norris and the Hart in 2000. He continued to dominate until suffering an injury in 2011 that ended his career.

The player the Whalers got back in return was no slouch — it was Brendan Shanahan, who was inducted into the Hall of Fame on Tuesday. But Shanahan didn’t want to play in Hartford, and spent only a year there before forcing a trade to Detroit.

Randy Carlyle, 22 (Toronto Maple Leafs)



Carlyle was a promising young player on the Maple Leafs in the 1970s, so it goes without saying that they had to trade him. In this case, the deal was for Dave Burrows, who played just two years for Toronto.

Carlyle would go on to a 17-year career that included four All-Star selections and a Norris Trophy in 1981. He would also, of course, go on to a coaching career that brought him back to Toronto, where he currently serves as the Leafs’ head coach.

Leo Boivin, 22 (Toronto Maple Leafs)



OK, we’re reaching pretty far back into the history books on this one, but here it goes. Boivin had two full seasons with the Maple Leafs under his belt when he was traded a few weeks into the 1954-55 season in a deal that saw the Bruins send veteran Joe Klukay to Toronto. Klukay would play two more years in the NHL; Boivin would play 16.

The most memorable of those years would come in Boston, where he was named to three All-Star teams and would eventually serve as team captain. He’d also play for the Wings, Penguins, and North Stars before retiring in 1970. He was inducted into the Hall of Fame in 1986.

Ryan McDonagh, 20 (Montreal Canadiens)



OK, sure, the Habs shipped McDonagh to the Rangers only to see him develop into one of the league’s best young defensemen. But you have to give something to get something, and that means trading the occasional blue-chip prospect if it means you can acquire [checks trade details] oh, right.

Yes, this is the infamous Scott Gomez trade, in which the Rangers managed to unload what seemed like an untradable albatross of a contract on Montreal. Moving the contract was good enough. To get a young player like McDonagh in return was borderline larceny.

Honorable mentions: Sandis Ozolinsh, Dave Babych, Darryl Sydor, Luke Richardson

Goalies

Bernie Parent, 22 (Boston Bruins)



Parent debuted with the Bruins in 1965, playing 39 games as a rookie while splitting time with Eddie Johnston. He’d spend most of the 1966-67 season in the minors, and when it came time for the league’s first expansion draft during the 1967 offseason, the Bruins left him unprotected.

That was good news for the Flyers, who claimed him and watched him go on to win the starting job. By 1969, he had established himself as an All-Star, as the Flyers developed from expansion whipping boys into a legitimate Cup threat.

Parent ultimately backstopped Philadelphia to back-to-back championships in 1974 and 1975, the only two Cups in franchise history. He won the Conn Smythe both years, making him the first player to capture the honor in back-to-back seasons (only Mario Lemieux has done it since).

Parent would go on to have brief stops in Toronto and the WHA before returning to finish his career as a Flyer. He was inducted into the Hall of Fame in 1984.

Roberto Luongo, 21 (New York Islanders)



Yes, children, there was a time when it was actually possible to trade Roberto Luongo, and the Islanders did just that in 2000.

New York had taken Luongo with the fourth overall pick in the 1997 draft, at the time the highest pick ever used on a goaltender. But after two more seasons in junior hockey and a shaky rookie season in New York, the Islanders ran out of patience. At the 2000 draft, the Islanders used the no. 1 overall pick to anoint a new goalie of the future, Rick DiPietro.

The same day, they dealt Luongo and Olli Jokinen to the Florida Panthers for Mark Parrish and Oleg Kvasha in one of the most lopsided trades in recent NHL history. Parrish and Kvasha were nice additions, but Luongo went on to become one of the best goalies in the league while DiPietro eventually crashed and burned.

Honorable mentions: Billy Smith, Tom Barrasso, Gilles Meloche, Kirk McLean, Tomas Vokoun, Tuukka Rask

Coach

Scotty Bowman (St. Louis Blues)



And just for fun, let’s close with a coach. Obviously we won’t find many who meet our “under 25” criteria, but Bowman wasn’t that far off — he was named coach of the expansion Blues at the age of 34. He spent four years in St. Louis and made the finals three times, but left after the 1970-71 season to join the Canadiens. He’d go on to rack up 1,244 wins and nine Stanley Cups (plus a few more in front-office roles).

Good luck with this squad, Scotty. They all may have a chip or two on their shoulders.