1. Ray Bourque and Dave Andreychuk to the Avalanche from the Bruins for Brian Rolston, Samuel Pahlsson, Martin Grenier and a first-round pick; March 6, 2000After two decades spent redefining excellence in Boston, Bourque was finally put out of his Stanley Cup-less misery by Bruins owner Harry Sinden. The Avs saw the future Hall of Fame defenseman as a missing piece. Though they didn't win the Cup that season, Bourque immersed himself in the team's culture for the full campaign of 2000-01. The desire to win one for the highly regarded veteran served as a rallying point. In a touching moment, captain Joe Sakic handed the chalice to an emotion-wracked Bourque after their Game 7 finals win over the Devils.
2. Joe Thornton to the Sharks from the Bruins for Marco Sturm, Brad Stuart and Wayne Primeau; Nov. 30, 2005He was their captain and leading scorer, and the Bruins couldn't wait to get rid of him. Thornton, a former first overall pick, was deemed too soft and unmotivated to lead the Bruins after a dismal playoff against Montreal that may (or may not) have been influenced by a rib injury. That Jumbo Joe was dealt wasn't a shock. What was nearly unfathomable was that the Bruins chose to forego shopping him around the league. Still, the deal worked out fairly well for both sides. The B's used their freed-up cap space to sign Marc Savard, while the Thornton-led Sharks became one of the NHL's most dangerous teams...during the regular season, at least.
3. Chris Pronger to the Ducks from the Oilers for Joffrey Lupul, Ladislav Smid, a 2007 first-round pick, and a 2008 first-round and second-round pick; July 3, 2006You have to hand it to Brian Burke. As soon as Anaheim's GM heard rumors that Pronger's wife was Yoko-ing the defenseman's relationship with the Oilers, he put together a sizable package to bring Big Trouble to The Pond. It was a risky move. Lupul was coming off a 28-goal season, and moving three first-rounders (including Smid) guaranteed empty shelves in the prospect cupboard. Still, Pronger had been a monster in the 2006 playoffs, and he brought the truculence that defined how Burke wanted his Ducks to play. Though he stayed just three seasons, Pronger proved an astute acquisition. He led the franchise to its first Stanley Cup in 2007, the same year he was honored as a Norris Trophy finalist. He was named team captain the following year and finished among the league leaders in time-on-ice each season.
4. Roberto Luongo and Olli Jokinen to the Panthers from the Islanders for Mark Parrish and Oleg Kvasha; June 24, 2000Armed with the first overall pick in the 2000 draft, Islanders GM Mad Mike Milbury had his choice of dynamic scorers -- Dany Heatley or Marian Gaborik -- but was enthralled by DiPietro, the brash puck-moving stopper from Boston University. Milbury already had one of the game's best young keepers in Luongo, so rather than overload at the position, he sent Luongo to Florida with disappointing sophomore Jokinen. Luongo lived up to his promise and became an elite goaltender. Jokinen became an All-Star who led the Panthers in scoring five times. The oft-injured DiPietro had his mail forwarded to the trainer's room. Parrish became a serviceable secondary scorer, but Kvasha redefined plodding. Amazingly, Milbury lasted another six years on the job.
5. Tomas Fleischmann and first- and fourth-round picks to the Capitals from the Red Wings for Robert Lang; Feb. 28, 2004This was a less dramatic deal than, say, the August 2005 exchange that saw Ottawa send Marian Hossa to Atlanta for Dany Heatley, but the swap just ahead of the trade deadline exemplifies what every team hopes to accomplish when it dishes an established veteran for a handful of magic beans. In this case, the cash-strapped Caps dumped their leading scorer for a pair of players who are now part of the core of their Cup-contending squad. The fourth-rounder (Luke Lynes) was a flop, but Fleischmann has matured into an exciting, if raw, secondary scorer. And that first-rounder? The Caps used it to select Mike Green, the anchor of their blueline and one of the game's premier offensive defenders.
1. Marc Savard, Bruins; July 1, 2006Written off as too small by the Rangers and one-dimensional by the Flames, the crafty Savard finally emerged as an elite scorer in his third NHL stop, with the Thrashers. Questions persisted, though, as he entered free agency. Was he really an offensive sparkplug or merely a product of playing with Ilya Kovalchuk and Heatley? The Bruins bet $20 million over four years on the former, and reaped a big payoff. Savard has led them in scoring in each of his first three seasons (262 points in 238 games) and, to his credit, has evolved into a reliable two-way player under coach Claude Julien.
2. Tim Thomas, Bruins; Sept. 14, 2005Coming off an MVP season in the Finnish league, the 31-year-old Thomas blew off a secure deal with Jokerit for one last shot at his NHL dream. With Andrew Raycroft holding out, the Bruins were looking for some low-cost insurance between the pipes. Their one-year, $450,000 risk paid off for both sides. When the door opened, Thomas played well enough to turn Raycroft into trade bait and earned himself a permanent gig. Before long, he was established as one of the league's best and most exciting stoppers. A two-time All-Star, he entered this season as the reigning Vezina Trophy-winner and is a likely member of Team USA for the 2010 Olympics.
3/4. Brett Hull and Luc Robitaille, Red Wings; July 2001Getting sent home early by the hated Avalanche two years in a row was bad enough, but being spanked by the Kings in 2001 -- in the first round, no less! -- demanded swift, decisive action by GM Ken Holland. He dealt for top goalie Dominik Hasek, then took a Steinbrenner-esque dive into the free agent pool by adding a pair of aging 500-goal scorers to a club that was already buying Grecian Formula in bulk. Both legends responded to their two-year, $9 million deals with 30-goal seasons. Hull added 10 more to lead the team in the playoffs and Robitaille was also a key contributor to Detroit's 2002 Stanley Cup.
5. Chris Osgood, Red Wings; July 1, 2006Further proof that a free agent doesn't have to cost more than a private jet to make a dramatic impact. The Wings repatriated the oft-maligned Osgood from the Blues for $1.8 million over two years to serve as backup to Hasek. His first season was derailed by injuries, but Osgood earned his keep in 2007-08. With Hasek sidelined by a bad back, Osgood played well enough to earn a spot in the All-Star Game. Hasek's reputation earned him the start when the playoffs began, but when he struggled against the Predators in the first round, Osgood stepped back between the pipes, going 14-4 with a 1.55 GAA to lead the Wings to the Cup. And while Osgood was brutally inconsistent last season, he again found his form in the playoffs. Though the Wings failed to repeat, his sparkling play made him the team's leading Conn Smythe-contender had they beaten the Penguins in Game 7 of the final.
1. Sean Avery, Stars; July 2, 2008Upon learning that his team had signed the NHL's most notorious pot-stirrer for $15.5 million over four years, one of the Stars responded, "You've got to be (blanking) kidding me." The team's core was determined to alienate Avery, and he made no effort to fit in. (He was often seen wandering American Airlines Center with his iPod as the Stars prepped for games.) His high-profile role in a Slap Shot-style, brawl-filled game against the Bruins on Nov. 1 prompted veteran Mike Modano to lament, "It was one of the most embarrassing things I've seen. If that's what we're going for, then they need to find me an office job.'' Avery's infamous "sloppy seconds" remark about his ex-girlfriends prompted the Stars to make the rift permanent in December. Avery's totals: three goals, 10 points, 23 games and $1.937 million paid each of the next three years while he skates for the Rangers.
2. Bobby Holik, Rangers; July 1, 2002After missing the playoffs the previous five seasons, Rangers GM Glen Sather saw Holik as the star of a Broadway revival and hired him with a five-year, $45 million deal. Sure, the former Devil was the premier defensive center of his time, a shutdown specialist who'd helped New Jersey to a pair of Cups, but his superstar pay grade suggested a player who could put buns in the seats or, at least, pucks in the net. Holik did neither and was bought out after just two seasons, forever enshrined as the symbol of pre-lockout salary bloat.
3. Jeff Finger, Maple Leafs; July 1, 2008There's nothing like a bold move on the first day of free agency to mobilize the fan base. Except in this case, Toronto's fans were mobilized to Google the signee's name to figure out exactly who the hell this Finger guy was. After just one serviceable season of NHL duty, the 28-year-old defender was the beneficiary of a one-team bidding war that, through no fault of his own, turned his name into a punchline when was awarded a four-year, $14 million contract. To no one's surprise, Finger has remained a borderline player who this season has spent almost as much time in the press box as in the lineup.
4. Pierre Turgeon, Stars; July 1, 2001It wasn't that it was a bad idea to sign the crafty Turgeon, who was coming off a 30-goal, 82-point season, for five years and $32.5 million. It's that it was a bad idea for the Stars, who already dressed two elite centers in Modano and Joe Nieuwendyk (and later, Jason Arnott), but had neither the ice time nor the productive wingers to make the most of a third. Little wonder that Turgeon's offense (and soon, his effort) dropped precipitously. To make matters worse, his hefty contract put the team in a financial bind that forced them to cut captain Derian Hatcher loose in 2003. Turgeon himself was set adrift, albeit with a hefty buyout check in his pocket, after the third disappointing year of the deal.
5. Martin Lapointe, Bruins; July 2, 2001Lapointe's career year (27 goals and 57 points) earned him a hefty raise in free agency ($21 million over four years), but Boston's offer was an indefensible sum to pay a checking line winger. Of course, the Bruins trumpeted the value of his intangibles and, to his credit, Lapointe provided a diligent effort and strong leadership while wearing black and gold. But his production returned to its traditional spot along the lower end of the curve and he ended up scoring just 40 goals over three seasons before being cut loose by the Bruins after the lockout.
1. Alexander Svitov, Lightning, third overall, 2001Blessed with a hulking frame and a physical, two-way game cultivated for three years in Russia's top league, Svitov was expected to make an immediate impact. Unmotivated and frustrated by the cultural transition to North America, he spent parts of three seasons in the NHL, scoring 13 goals and earning 223 penalty minutes. At least trading him paid off. He was dealt to Columbus for veteran defenseman Darryl Sydor, who played a key role in Tampa's 2004 Stanley Cup.
2. Hugh Jessiman, Rangers, 12th overall, 2003Nicknamed Huge Specimen by the scouts who birddogged his games at Dartmouth, the 6-6, 220-pound winger had the build of a young Todd Bertuzzi and a born-in-Manhattan backstory that made him irresistible to the Rangers, who projected him as a superior prospect to Zach Parise, Ryan Getzlaf and Mike Richards, among others. Five years later, his potential submarined by labored skating and limited hockey sense, Jessiman was dealt to the Predators for future considerations. He left burdened with the ignominious distinction of being the only first-rounder from the 2003 draft not to play a game in the NHL.
3. Al Montoya, Rangers, 6th overall, 2004After guiding Team USA to its first World Juniors gold medal with an MVP-caliber performance in 2004, Montoya was cemented as the best goalie in the draft. Scouts raved about his confidence and puckhandling skills, comparing him to Marty Turco and prompting the Rangers to select him as the best player available even though they already had Henrik Lundqvist and Dan Blackburn in their system. Naturally, the presence of King Henrik eroded Montoya's value as an asset. Unable to crack the NHL lineup, Montoya was buried in the minors where his progress was slowed by groin problems and confidence issues. When the Blueshirts finally dealt him, it was for spare parts rather than the key piece of the puzzle they always thought he'd return. He's since made his NHL debut with Phoenix, but is currently struggling to regain his game in the AHL.
4. Igor Knyazev, Hurricanes, 15th overall, 2001The 2001 draft was hardly one for the ages, but more than half the players in the first round provided at least 250 games of NHL service. The Hurricanes might have acquired one if they hadn't insisted on ignoring warning signs. Despite being a staple of Russian international teams, Knyazev was left off the 2001 World Juniors squad. The reasons for the snub were never revealed, but there were rumors of off-ice disciplinary issues. He spent two unhappy seasons in the minors before heading back to Russia without ever playing an NHL game.
5. Petr Taticek, Panthers, ninth overall, 2002The Panthers arrived at the draft with a pair of top-10 picks in their pocket and a real chance to breathe some life into their moribund franchise. Their first choice, Jay Bouwmeester, quickly matured into one of the game's top stars. But with the ninth overall pick, Florida tabbed Taticek, a Sault Ste. Marie Greyhounds center touted for his playmaking and hockey sense. What he lacked was a work ethic and tolerance for physical punishment. After floating through three games with the Panthers, he was dealt to Pittsburgh for another first-round flop, Richard Jackman.
1. Henrik Lundqvist, Rangers, seventh round (205th overall), 2000If New York's scouts were as brilliant as they've been made out to be, Brandon Snee would be basking in the bright lights of Broadway. Snee was the goaltender tabbed by the Rangers a full 63 picks ahead of the lightly regarded Lundqvist, whose career highlight was a 12-game stint in the ill-fated WHA2. But it was Lundqvist who developed into one of the premier stoppers of his generation. A finalist for the Vezina Trophy in each of his first three seasons, King Henrik also was the first goalie to win at least 30 games in each of his first four seasons.
2. Joe Pavelski, Sharks, seventh round (205th), 2003Scouts at the time agreed that Pavelski was developing a well-rounded offensive game with Waterloo of the USHL. The other point of consensus: his skating wouldn't cut it in the NHL. "Awkward stride," wrote one scout. "Lacks explosiveness," reported another. But Pavelski proved to be one of those players whose value exceeds the sum of his parts. A champion at every level he played, Pavelski learned what it took to compete. He became an elite face-off man and an exceptional defensive presence. "He could always score," said one scout, "but he figured out there was more to being an NHL player. You don't see that that often from guys that low in the draft."
3. Mark Streit, Canadiens, ninth round (262nd), 2004The company line is that NHL teams don't care where a prospect comes from, as long as he can play. Truth is, that line didn't exactly apply to Switzerland when Streit first became draft eligible in 1995. The belief was that an easy schedule and favorable tax situation made Swiss players less likely to bolt the Nationalliga for the NHL, but Streit shattered that prejudice by paying his dues. His pre-draft apprenticeship in the AHL proved his ability to adapt to the North American game, but it was a strong World Championship performance that finally convinced the Habs to take a chance on him. Although the team wavered on where to play him, Streit eventually emerged as an elite offensive defenseman, guiding Montreal's power play to the top of the league rankings.
4. Lubomir Visnovsky, Kings, fourth round (118th), 2000The 2000 World Championships provided a bittersweet experience for Visnovsky. The 24-year-old was crushed when his Slovakian side lost to their archrivals from the Czech Republic in the gold medal game, but his strong play in the tournament convinced the Kings to overlook his Olive Oyl-build and give him a chance to prove himself in the NHL. The pick paid instant dividends as Visnovsky earned a spot on the 2001 NHL All-Rookie Team with a 39-point season and became one of the game's premier puck-moving defenders.
5. Pekka Rinne, eighth round (258th), Predators, 2004It's not a surprise that Rinne was plucked so late, but that his name was called at all. Bypassed in each of his first three years of eligibility, he had settled into a career as a seldom-used understudy in the Finnish SM-Liiga when his break finally came. The veteran No. 1 at Karpat, Niklas Backstrom, caught the eyes of NHL birddogs looking for the next ready-to-serve free-agent netminder. While scouting Backstrom, the Preds were sold on the potential of Rinne, even though their exposure was limited mostly to practices and warm-ups. Now 27, Rinne has fought through Nashville's crowded field of netminding prospects to become what he couldn't be in Finland: an elite starting goalie.