Re-Drafting The First Round Of The Terrible 1999 NHL Entry Draft

Is the 1999 NHL Entry Draft the worst of all-time? If you look at just the first round alone, it is definitely up there among the worst NHL Drafts. Three players drafted in the first round never even played a single NHL game, while another nine players failed to play at least 82 career NHL games. The three goaltenders taken in the first round played a combined grand total of 16 games. The 1999 draft also included one of, if not biggest first overall draft busts in NHL history.

Trying to select 28 of the best players to come out 1999 draft was a tough task. Of the thirty players on this list, only the top four players were safely, at one point, the best player on their respective teams. While some other players on the list had pretty good careers, most were nothing more than complimentary players at best. The draft was so weak that a player who was nothing more than a goon on the ice during his career made the list.

If there is one positive thing that sticks out about the 1999 draft, it is the amount late round draft steals. Players who were taken late in the draft have defied the odds and have turned out to be the best players to come out of the draft. The first overall pick on this list was actually drafted all the way back in the seventh round. There are also three players on this list who might one day make it to the Hockey Hall of Fame, but are far from surefire locks.

Here is how the 1999 NHL Entry Draft would go if it was redone today. The player’s actual selection number overall is in parenthesis.

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28 Atlanta Thrashers: Henrik Zetterberg

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Original Pick: Patrick Stefan

Henrik Zetterberg is one of the greatest NHL Draft steals of all-time, as he was originally taken by the Detroit Red Wings all the way down in the seventh round. Despite the low odds of ever making it to the NHL, Zetterberg has played over 900 NHL games and counting, while 115 out of the 209 players selected before him, never played a single NHL game. He might not have the most career points out of any player in the 1999 draft (he's third, behind a pair of twins), but his impact on the ice is about more than points.

His defensive game is spectacular, as he knows where to be on the ice at all times. When the pressure is on, he always steps up his game. There is no better evidence than in the 2008 playoffs, when he scored 27 points, leading the Red Wings to the Stanley Cup. Zetterberg was awarded the Conn Smythe Trophy as the playoff MVP for his efforts. Zetterberg will go down as one of greatest Swedish players to ever play in the NHL. A induction into the Hockey Hall of Fame is definitely not out of the question for him.

27 Vancouver Canucks: Daniel Sedin

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Original Pick: Daniel Sedin

As the General Manager of Vancouver Canucks back in 1999, Brian Burke made a bold decision to move up in the draft and select both of the Sedin twins. While their careers got off to bit of a rocky start, they have since proven to be by far the best offensive players to come out of the 1999 NHL Entry Draft.

Other than bragging rights, it didn't really matter which brother was selected first, but it just so happened that Daniel Sedin was taken first originally, so we'll stick with it. Daniel had a very good rookie season, scoring 20 goals and 34 points. Daniel struggled to put the puck in the net in his second season, scoring only nine goals. He wouldn't actually have another 20-plus goal season until his breakout year in 2005-06. In 82 games, he put up 71 points, proving he was indeed worthy of his number two overall selection.

Daniel has proven to be more of the finisher when it comes to the twins. Daniel is currently the all-time Canucks goal scoring leader. He scored a career high 41 goals in the 2010-11 season. His 104 points that same season were good enough to win the Art Ross Trophy as the leagues top point producer.

26 Vancouver Canucks: Henrik Sedin

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Original Pick: Henrik Sedin

Henrik Sedin, like his brother, had a slow start to his NHL career. He averaged just under forty points in his first four seasons with Vancouver. His breakout year was also in 2005-06, when he scored a career high 75 points, which was a 28 point increase from his previous high. Henrik had a career year in 2009-10, when he led the league in points with 112. He would win the Hart Trophy that same season as the league's most valuable player.

Henrik has been the setup man for most of Daniel's goals. He currently leads the Canucks in all-time assists, as well as points. He has amazing playmaking ability that has provided average goal scoring players like Anson Carter and Taylor Pyatt career years.

The Sedin's have created themselves great NHL resumes and one day could be inducted into the Hockey Hall of Fame. Although their resume is missing one important thing, that being a Stanley Cup.

25 New York Rangers: Ryan Miller

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Original Pick: Pavel Brendl

The Buffalo Sabres ended up getting a huge draft steal when they took Ryan Miller in the fifth round. Miller became the starting goalie the Sabres were looking for ever since they lost Dominik Hasek. He would play parts of 11 seasons in Buffalo. He currently holds most Sabres franchise goaltending records, including most wins with 284. The best year of his career was in 2009-10, where he was absolutely stellar in net. He compiled a record of 41-18-8 with 2.22 GAA and a sparkling .929 save percentage. Miller is now a member of the Vancouver Canucks, where at the age of 35, he is still providing above average goaltending.

Besides Patrik Stefan, Pavel Brendl was the biggest draft bust coming out of the 1999 NHL Draft. He was an absolute stud in the WHL, recording 320 points in 178 games. However, in 78 career NHL games he recorded a petty 22 points.

24 New York Islanders: Craig Anderson

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Original Pick: Tim Connolly

Craig Anderson is the only player on this list to be drafted twice into the NHL. He was originally drafted by Calgary in the third round of the 1999 draft, but the Flames opted not to sign him. Anderson proved that the Flames made a mistake not signing him, as the following season he would be named OHL Goaltender of the Year. Anderson re-entered the draft in 2001 and was selected by the Chicago Blackhawks, 77th overall.

Anderson spent time in the minors and as a backup before finally making a name for himself with the Colorado Avalanche in 2009-10. He played a career high 71 games, surpassing his pervious high of 31, which he had only achieved the year prior. He posted an impressive 38-25-7  record with a 2.64 GAA, along with a .917 save percentage. Anderson only played a half season more with the Avalanche before he was traded to the Senators. He has battled with some injuries during his time in Ottawa, but when he is healthy his numbers have been fairly impressive.

23 Nashville Predators: Barret Jackman

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Original Pick: Brian Finley

Barret Jackman has been as steady as a defender as there is in the NHL, ever since he entered the league in 2002, after being selected 17th overall. He was already rock solid on the blueline in his rookie season, playing like a veteran, on way his way to capturing the NHL Rookie of the Year. Jackman spent 12 seasons with the Blues, providing great veteran leadership on the back end. Although he lacks much offensive talent, his defensive game has allowed him to have a long successful NHL career.

Brian Finley had a fantastic junior career with the Barrie Colts of the OHL. He played especially well during his draft year of 1998-99. He compiled a record of 36-10-4, with an amazing 2.66 GAA with a solid .913 save percentage. Those numbers were good enough for Finley to be the first goalie taken in the 1999 draft. However, Finley had a tough time adjusting to the pro game, only managing to play four NHL games in his career. The goaltender suffered many injuries throughout his career, and he was eventually forced out of the game in 2007.

22 Washington Capitals: Martin Havlat

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Original Pick: Kris Beech

When healthy, Martin Havlat (originally selected 26th overall) has been a dynamic offensive force. He has shown he is capable of being at point per game player. The problem is that Havlat has not played a full season even once during his 15 career NHL seasons. He has missed well over 300 games in his NHL career due to injury. Havlat did play 81 games with the Chicago Blackhawks back in 2008-09 and had the best offensive year of his career, scoring 77 points. If only he was able to stay healthy, he could of been ranked even higher on this list.

Kris Beech had a pretty good rookie season with the Pittsburgh Penguins in 2001-02, recording 10 goals and 25 points. The following year Beech struggled, recording just one point in twelve games with the Penguins. He wouldn't make it back to the NHL full time until the 2006-07 season with the Washington Capitals. In 64 games he recorded a career high 26 points. Unfortunately, Beech would never have a more productive NHL season than that. He has since played in the minors, as well as all over Europe.

21 New York Islanders: Radim Vrbata

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Original Pick: Taylor Pyatt

Radim Vrbata has been an underrated goal scorer throughout his NHL career, after being selected in the seventh round. He scored 18 goals in just 52 games during his rookie year with Colorado. Vrbata struggled a bit to put the puck in the net following his rookie season, but he eventually found his footing. Vrbata's best season was with the Phoenix Coyotes in 2011-12 when he scored 35 goals, including a league high 12 game winning goals.

Vrbata signed with the Vancouver Canucks in 2014, where he was lucky enough to play with felllow 1999 NHL draftee's Henrik and Daniel Sedin. He had a career year with the Canucks, recoding another 30-plus goal season while recording a career high 63 points. His second year with the Canucks was an off year for him as he only registered 27 points in 63 games. Vrbata has proven to be one of the top goal scorers to come out of the 1999 draft.

20 New York Rangers: Martin Erat (191)

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Original Pick: Jamie Lundmark

Martin Erat spent eleven seasons as a Nashville Predator where he established himself as one the best players in franchise history, after being a late round selection for them. In 723 games with the Predators he scored 481 points, which currently ranks second on Nashville's all-time scoring list.

Erat was traded to the Washington Capitals in 2013 where he struggled, scoring just two goals in 62 games. Erat would play one more mediocre season with the Coyotes in 2014-15, before going to the KHL. Erat's career may have taken a downwards turn once he left the Predators, but you cant take away the significant impact he had during his time in the Music City.

Jamie Lundmark was an offensive juggernaut during his time in the Western Hockey League. In 152 games he put up a fantastic 216 points. Lundmark wasn't able to translate his junior success to the NHL. Although he was a very productive minor league player, he never scored more than the 19 points he had during his rookie year with the New York Rangers in 2002-03.

19 New York Islanders: Chris Kelly

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Original Pick: Branislav Mezei

Chris Kelly has been able to have a long NHL career, after being selected in the third round, due to the fact that he's such a versatile player. He can be slotted anywhere in the lineup and is responsible at both ends of the ice. Kelly played six seasons with the Ottawa Senators before he was traded to Boston in 2011, where played a important role in the Bruins winning the Stanley Cup. Recently Kelly has struggled with injuries as he only managed to play 11 games in the 2015-16 season.

Branislav Mezei was a big hulking defensman, who showed a bit of an offensive side to his game in junior. He ended up playing 240 career NHL games, but his lack of offensive production proved he was too one dimensional of a player. Mezei would still manage to go on to have a decent career outside the NHL. He currently plays with HK Nitra of the Slovak Extraliga.

18 Calgary Flames: Jordan Leopold

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Original Pick: Oleg Saprykin

Jordan Leopold was a very reliable defender during 13 seasons in the NHL (originally selected 44th overall). He was on the move a great deal during his career, playing for eight different teams. The best season of his career was arguably the 2003-04 season, just the second of his NHL career. While playing for the Calgary Flames, he recorded 33 points. He also helped the Cinderella story Flames make it all the way to Game Seven of the Stanley Cup Finals. Leopold finished off his NHL career in 2014-15 playing for his hometown Minnesota Wild.

Oleg Saprykin showed flashes of his great offensive talent in the NHL, but never seemed to put it all together. His best year came in 2006-07, where he recorded 36 points with Phoenix and Ottawa. Despite having a pretty good year, that would be his last season in the NHL. Since leaving North America, Saprykin has played in the KHL.

17 Florida Panthers: Mike Comrie

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Original Pick: Denis Shvidki

Mike Comrie (selected 91st overall) proved he belonged in the NHL after only his first full season in 2001-02. In 82 games with the Edmonton Oilers, he scored 33 goals and had 60 points. After moving on from Edmonton, Comrie would have some more success in Phoenix, once again topping the 60 point mark. After leaving the Coyotes, Comrie had some decent success with the Ottawa Senators and the New York Islanders. Sadly Comrie's career would be cut short by hip problems as he announced his retirement in 2012.

Denis Shvidki spent just four seasons playing in North America. He spent the majority of his time in the AHL. His best season in the NHL came during his rookie year 2000-01 with the Panthers. Shvidki recorded six goals and 10 assists in 43 games, all career highs. He left North America when the NHL went into a lockout in 2004, when he went on to play in Russia and Germany.

16 Edmonton Oilers: Tim Connolly

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Original Pick: Jani Rita

Tim Connolly was a very offensively talented player, but he was not able to stay healthy for the life of him. He came to NHL right out of junior (5th overall) and had great rookie season, scoring 34 points, which was good enough for third on the Islanders. Connolly missed the entire 2003-04 season due to post concussion syndrome. Fortunately he was able to make a comeback He scored a career high 65 points with Buffalo in 2009-10. Sadly it wasn't too long before he once again found himself on the sidelines and he was forced to retire in 2013.

Jani Rita had success in North America, but too bad for him it was in the AHL, not NHL. In 204 career, AHL games he recorded 131 points. In 66 career NHL games Rita only recorded a measly 14 points. After the 2005-06 season with the Pittsburgh Penguins, Rita left the NHL for Europe.

15 San Jose Sharks: Niclas Havelid

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Original Pick: Jeff Jillson

Niclas Havelid was already twenty-six-years-old when the Ducks took him in the third round. The defenseman spent five seasons in Anaheim, establishing himself as a solid all-around player. In 2002-03, he had scored a career high 11 goals and 33 points. He also suited up for 21 playoff games, helping the Ducks reach the 2003 Stanley Cup Finals, where they would unfortunately lose to the Devils in seven games. He would play for the Atlanta Thrashers and the New Jersey Devils before finishing off his career in Sweden.

Jeff Jillson was a college star for the University of Michigan. In three seasons at Michigan, the defenseman recorded a combined 88 points. He had a solid rookie year with San Jose in 2001-02, scoring 18 points in just 48 games. Unfortunately, Jillson was not able to recreate the success he had during his rookie year. He had stints with Boston and Buffalo but mostly found himself in the minors.

14 Phoenix Coyotes: Ryan Malone

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Original Pick: Scott Kelman

Ryan Malone (115th overall) proved that he could be a force every time he was on the ice. He was a defensively strong player who could kill penalties. However, his greatest asset may have been his ability to put the puck in the net. During his ten-plus NHL seasons he was a six time 20-plus goal scorer. Malone's best season came in 2007-08 where he scored 27 goals and 51 points. Malone also recorded 16 points in the 2008 NHL playoffs, helping the Penguins make it to the Stanley Cup Finals. Unfortunately for Malone, his off ice problems got the best of him and shortened what was once a solid career.

Scott Kelman spent parts of six season's playing in the Western Hockey League before turning pro in the 2001-02 season. Despite putting up some decent numbers in the minors, he never played a single game in the NHL. Kelman would finish his playing career having played for a whopping 13 different professional teams.

13 Carolina Hurricanes: Nick Boynton

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Original Pick: Dave Tanabe

During the height of his career, Nick Boynton (21st overall) was known for being a great physical force but could also chip in offensively when needed. His best years came as a member of the Boston Bruins, where he scored a career high 30 points during the 2003-04 season. After his run in Boston, Boynton struggled with consistency and found himself always on the move. Boynton capped of his career by winning a Stanley Cup in 2010 with the Chicago Blackhawks as a depth defenseman.

Dave Tanabe showed a lot of promise during his short time in the NHL. The defenseman scored 29 points in his first full NHL season with the Carolina Hurricanes. Tanabe would play six more NHL seasons with Phoenix, Boston, as well as a second stint with Carolina. Sadly, Tanabe's career was cut short due to concussion problems in 2008. After his playing career he took up coaching before becoming a player agent.

12 St.Louis Blues: Niklas Hagman

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Original Pick: Barret Jackman

Niklas Hagman was originally taken by the Florida Panthers in the third round. He had been a star player for HIFK Helsinki Jr. of the top Finnish junior league. He made a full-time transition to the top Finnish men's league in 2000-01, where he excelled by scoring 46 points in 56 games. He would play parts of four season with the Panthers where he put up mediocre numbers. It wasn't until he was traded to the Dallas Stars in 2005, that he started to break out. In his third season with Dallas in 2007-08, he scored a career high 27 goals.

Hagman would sign with Toronto in 2008, where he would have two consecutive twenty-plus goal seasons. He would be traded to the Calgary Flames in 2010 and his career took a downwards fall. When the NHL entered a lockout ahead of the 2012-13 season, Hagman left for Europe and never came back.

11 Pittsburgh Penguins: Mike Commodore

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Original Pick: Konstantin Koltsov

Mike Commodore's best years came earlier on during in his NHL career. Originally selected 42nd overall, he made a name for himself as a solid defenseman during Calgary's run to the 2004 Stanley Cup Final. Although he fell short with Flames, he was able capture the Cup with the Carolina Hurricanes in 2006. His best years by far were with the Hurricanes. He had a career high 29 points in 2006-07. After Commodore left the Hurricanes, he battled inconsistency and he also failed to stay healthy. By the 2013-14 season he was out of the league and playing in the KHL.

Konstantin Koltsov had pretty decent rookie season for the Penguins. He recorded 29 points while suiting up for all 82 regular season games. He played just one more season in the NHL, where his offensive production was almost non existent, scoring just nine points. Koltsov has continued to play in Russia for the past decade.

10 Phoenix Coyotes: Derek MacKenzie

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Original Pick: Kirill Safronov

Derek MacKenzie (128th overall) spent years working his butt off in the minors, before finally getting a permanent NHL spot in 2009-10 with the Columbus Blue Jackets. He has been able to be an effective NHLer because of his great face-off and defensive skills. MacKenzie has also shown he can put the puck in the net when needed, scoring a career high nine goals on two different occasions.

Kirill Safronov spent time developing in his native home of Russia before making his North American debut with the Quebec Remparts of the QMJHL. The defenseman had a great year with Quebec, scoring 43 points in 55 games. He turned professional the following season and would end up just playing four season in North America. He spent the majority of his time in the minors, but did get into 35 career NHL games, where he put up a measly four points. When the NHL entered a lockout in 2004, Safronov went back home to Russia where he remained until the end of his playing career.

9 Buffalo Sabres: Douglas Murray

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Original Pick: Barrett Heisten

Douglas Murray (241st overall) didn't make his NHL debut until the 2005-06 season, but he immediately established himself as one of meanest defenseman in the NHL. His body was built more like an offensive lineman in football than that of a hockey player. Everybody knew to keep their head up when Murray was on the ice. Murray spent parts of eight seasons as a member of the San Jose Sharks, where he appeared in an impressive 57 playoff games. He would end his NHL career after playing for the Montreal Canadiens in 2013-14.

Barrett Heisten never ended up signing with the Sabres and instead signed with the Rangers as a free agent. After playing one season with the WHL's Seattle Thunderbirds, he made his debut with the New York Rangers in 2001-02. He would play ten games with the Rangers where he went pointless. Heisten's games with New York would end up being the only NHL games of his career, as he spent the rest of his career in the minors.

8 Boston Bruins: Adam Hall

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Original Pick: Nick Boynton

Adam Hall (52nd overall) spent four years playing for the Michigan State Spartans, where he proved he had the abilty to score goals. In 159 games with Michigan, he scored 79 goals.

Hall also showed his goal scoring ability during his first three seasons of his NHL career with the Nashville Predators. He had the best offensive years of his career with the Predators. Hall scored 16 goals in his rookie year of 2002-03, which would end up being a career high for him. In 233 games with Nashville, Hall scored 43 goals. In the 448 games after he left Nashville, he would only score a combined 26 goals.

Although Hall's numbers went down as his career progressed, he was still able to become a valuable role player for seven different NHL teams. He was Tampa Bay's Bill Masteron Memorial Trophy nominee in 2010-11, which is given to the player who is the most dedicated to the game of hockey. Hall had spent the 2009-10 season in the minors but made an NHL comeback and played in all 82 games of 2010-11 season.

7 Philadelphia Flyers: Alex Auld

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Original Pick: Maxime Ouellet

There was a brief moment in time when it looked like Alex Auld was destined to become an NHL starter for good. In 2005-06 with the Vancouver Canucks, he played a whopping 67 games. His previous career high was just six. However, the Canucks shipped him off to Florida the next season. Auld had all the opportunity to claim the number one goalie spot with the Panthers, but failed to do so. Auld would still find a role in the NHL for the next five seasons as a more than capable backup. He played his last NHL season with the Ottawa Senators in 2011-12, before playing one more hockey season in Austria.

The Philadelphia Flyers have not had too much success when it comes to drafting goalies and Maxime Ouellet is evidence of that. Ouellet was able to get into 12 NHL games with three different teams. The goaltender wasn't able to make much of an impact while in the NHL, and mostly found himself in the minors.

6 Chicago Blackhawks: Frantisek Kaberle

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Original Pick: Steve McCarthy

Frantiskek Kaberle is the older brother of Tomáš Kaberle. "Frank" was actually drafted (76th) three years after the younger Tomas, who was drafted in 1996. Frank had an solid but injury plagued career as an offensive defenseman. His best season was with the Carolina Hurricanes in 2005-06 when he recorded a career high 44 points. Kaberle also was credited with scoring the Stanley Cup winning goal in game seven against the Edmonton Oilers. Kaberle would finish off his playing career in the Czech Republic before hanging up his skates after the 2011-12 season.

Steve McCarthy was at best a depth NHL defenseman. His best season came in 2005-06 when he notched nine goals and 17 points in a career high 67 games played. He last played in the NHL with the Atlanta Thrashers in 2007-08. Since leaving the NHL, McCarthy has had stints in both Russia and Switzerland, but never had much success.

5 Toronto Maple Leafs: Taylor Pyatt

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Original Pick: Luca Cereda

Taylor Pyatt, the 8th overall pick in this draft, showed flashes of being a top six forward, but could never put it all together on a consistent basis. He had the rare combination of size and skating ability. He had a career year in 2006-07 when he scored 23 goals, although it helped that he played on a line with the Sedin twins.

In 2009, hockey took a back seat in Pyatt's life as his fiance was tragically killed in a car accident. To his credit Pyatt continued to play and had some of the best years of his career playing with the Phoenix Coyotes. In 2011-12 he played a career high 16 playoff games helping the Coyotes make it all the way to the Conference Finals.

Luca Cereda never got a chance to live out his dream of playing in the NHL, as he was forced to retire due to a heart condition. Cereda has since took up coaching in his native home of Switzerland.

4 Colorado Avalanche: Radek Martinek

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Original Pick: Mikhail Kuleshov

Radek Martinek (228th overall) was a solid all-around defenseman who played all but seven of his 486 career NHL games with the Islanders. His best season came in 2005-06, where he scored 17 points in 74 games. Martinek could have had much more production during his NHL career, but his biggest downfall was the fact he was never able to stay healthy. His body was just not built to play the hard hitting North American style of game. During his prime years from 2002 to 2011, he missed 256 out of a possible 656 games due to injury.

Mikhail Kuleshov spent parts of five seasons playing in North America. He played the majority of his time with the Hersey Bears of the American Hockey League. He struggled to adapt to the North American game as his numbers were mediocre at best. Kuleshov did manage to get into three games with the Avalanche in 2003-04, but failed to register a point.

3 Ottawa Senators: Patrik Stefan

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Original Pick: Martin Havlat

Patrik Stefan will go down as one of the worst first overall picks in NHL history. Although the 1999 draft was so poor that Stefan still earns a spot on this list. There was high expectations for Stefan heading into his first season with Atlanta Thrashers, but he didn't live up to them at all, scoring just five goals and 25 points. His production would eventually go up as he scored a career high 40 points in 2003-04. Stefan was traded to the Dallas Stars in 2006 where he would play the final 41 NHL games of his career while only scoring 11 points.

Stefan will be remembered as one of the biggest draft busts in NHL history, but he will be most remembered for his failed empty net goal attempt against the Edmonton Oilers in 2007. It's a play that will find itself on sports blooper reels for years to come.

2 New Jersey Devils: George Parros

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Original Pick: Ari Ahonen

George Parros was one of the most popular tough guys during his nine NHL seasons. He wasn't afraid to fight anyone in the league, which made him quite the popular player by teammates and fans alike. The man who became known more for his moustache than his play on the ice was lucky enough to get his name on the Stanley Cup while playing for the Anaheim Ducks in 2007. Unfortunately, Parros suffered many brutal fight-related concussions during his career. He suffered his last one in a fight against Eric Boulton, which would ultimately end his career.

Ari Ahonen already had an uphill battle in New Jersey with Martin Brodeur solidly entrenched in the Devils net. He would play five fairly poor seasons in the AHL for the Albany River Rats, compiling an abysmal combined AHL career record of 51-105-16. He left for Europe after the 2005-06 season, having never appeared in a single NHL game.

1 New York Islanders: Tom Kostopoulos (204)

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Original Pick: Kristian Kudroc

Despite being a seventh round draft pick, Tom Kostopoulos managed to carve out a decent NHL career. He was never able to put up big numbers, but played a valuable energy line role. He also wasn't afraid to stand up for his teammates. His best year offensively came during his rookie season in 2003-04 while playing for Pittsburgh, where he scored a career high 22 points in 60 games. Kostopoulos would actually score 22 points on four different occasions during his NHL career. Although it looks like his NHL days are over, he has still provided solid veteran play in the AHL.

The Islanders traded Kristian Kudroc to the Lightning before he even played a game with the team. He would play 22 games in his rookie NHL season, which unfortunately for him would be a career high. The NHL might have not been a fit for Kudroc, but he still managed to have a long career in Europe.

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