Revisionist History: Where These 20 NHL Draft Failures Should Have Been Drafted

“Hindsight is 20/20”. It’s easy for us to look back now on what people should have done years ago. We should accept that people make mistakes. Or maybe we should really dig deep into the research and figure out why certain people made certain mistakes and how we can avoid making them again. It doesn’t do a lot of good to simply say, “That was stupid. You should have done this instead”. It doesn’t do a lot of good...but it sure is fun. And nowhere is that truer than when examining sports drafts.

Drafting is incredibly tricky because there’s no way of knowing how a young player is going to develop. A hockey player who was great in junior hockey might not be able to cope with the grind of the big leagues. We need to remember that these are real humans with real variables. Real life is not like the NHL 17 video game. You can’t simply look at the “potential” rating for each player and draft accordingly. That’s why it’s nice to hear about great players who were drafted way down like Pavel Datsyuk, or who were never drafted at all like Martin St. Louis. But it’s even more fun to look at the NHL teams who had a chance to draft a great player but instead took a dud. So let’s kick up our feet, re-examine where some of the NHL’s biggest draft failures should have been drafted, and feel good about ourselves.

20 Jonathan Drouin (2013 - 3rd Pick)

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Should Have Been: 13th Pick - Winnipeg Jets

Okay, so maybe it’s a little premature to classify Jonathan Drouin as a draft failure. The French-Canadian has demonstrated that he has a tremendous amount of skill and he can still become a star. Indeed, he was a key player in the playoffs last season in Tampa’s run to the conference finals. So why is he on this list? Because of what happened before that. In his first season with the Lightning, Drouin had 32 points in 70 games, decent, but that only four of those 32 points were goals was worrisome. He ran into injury troubles in his second season and was assigned to the Lightning’s AHL affiliate, Syracuse, for conditioning, but he never showed up. What followed for months was Drouin speaking through his agent about an impending trade that never was. Drouin had asked for a trade in November and was now refusing to play, causing no small amount of headaches for Tampa GM Steve Yzerman. Drouin eventually relented and reported to Syracuse in March, and got called up to Tampa about a month later.

He’s a good player, but who knows when he might pull a stunt like that again. It looks like you’d have to drop down to the 13th pick (after Arizona’s Max Domi) to find a more appropriate slot for the volatile Drouin. That would make him a member of the Winnipeg Jets, who had the 13th overall pick that year.

19 Al Montoya (2004 - 6th Pick)

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Should Have Been: 31st Pick - Pittsburgh Penguins

Drafting goaltenders is always treacherous. After all, you can only play one goalie at a time. This tends to make a lot of general managers hesitant to pick a goalie early on in a draft. But the New York Rangers weren’t shy in 2004. They snapped up Al Montoya. And you can see why. Montoya had a promising career at the University of Michigan and represented the U.S. at the World Junior Championship. And to be fair to Montoya, he is an NHL player, which is more than you can say for a lot of the players on this list. The trouble is, Montoya has never been more than a back-up. He also took a long time to get going. He never even played for the Rangers. He was traded in 2008 to the Coyotes. 

Montoya is a decent goalie, but wasn't worth a first round pick. Going at the top of the second round seems like a better spot for him.

18 Tom Glavine (1984 - 69th Pick)

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Should Have Been: 171st Pick - Los Angeles Kings

You’re probably thinking, “Oh that’s funny, there was a hockey player with the same name as 1995 World Series MVP Atlanta Braves pitcher, Tom Glavine”. Nope. Same guy. That’s right, the man who would later become a Baseball Hall of Famer played center for his high school hockey team. He was so good that he was drafted by the L.A. Kings, the same year he was drafted by the Atlanta Braves in the MLB draft, a rare achievement. One wonders if the Kings were worried he would pursue baseball instead. But to be fair to the Kings, they didn't select him very high; they waited until the fourth round and picked him 69th overall. The only problem was there were a few hockey players they maybe should have picked instead who were still available. Players like, oh I don’t know, Brett Hull.

The Golden Brett notwithstanding, the 1984 draft makes a lot more sense if you switch L.A.’s 69th pick with their 171st pick - future NHL Hall of Famer Luc Robitaille.

17 Nail Yakupov (2012 - 1st Pick)

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Should Have Been: 23rd Pick - Florida Panthers

In 2012 the refrain was, “Fail for Nail”. Beleaguered fans of the teams at the bottom of the league that season, looking for a silver lining, were hoping their teams could do just a little bit worse. Worse enough to get the first overall pick in that year’s draft. Coming first overall would allow a team to draft highly touted Russian prospect Nail Yakupov. So you can’t really blame the Oilers; pretty much everybody thought Yakupov was a future star.

Well, a few years on any many would argue that Nail has Failed. Things started well enough, with Yakupov recording a decent 31 points in his first season, which was shortened due to a lockout. But Yakupov never again reached that level. The Oilers eventually got fed up with his mediocrity and basically gave him away to the St. Louis Blues this past offseason. Looking down the draft list for 2012, Yakupov seems better suited for the 23rd pick, behind Penguins’ defenceman Olli Maatta.

Going to the Panthers instead would have given Yakupov an eventual surrounding cast of Jonathan Huberdeau, Aleksander Barkov and Aaron Ekblad. He also wouldn't have been under the microscope like in Edmonton.

16 Dave Chyzowski (1989 - 2nd Pick)

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Should Have Been: 53rd Pick - Detroit Red Wings

The 1989 draft is difficult to assess. Mats Sundin went first, and that’s fair enough. After that, the first round looks pretty weak. There are several good names in the first round: Bill Guerin, Bobby Holik, Olaf Kolzig. But no glaring mistakes. So maybe we shouldn’t be hard on the Islanders. Yes, Chyzowski was a bust, but clearly many picks were. But then you go down the list and you see names like Adam Foote, Sergei Fedorov, and Pavel Bure and you wonder what the heck was going on. Were all the scouts drunk that year? First, remember that the U.S.S.R. was still around in 1989 (though it was falling apart) so many teams were leery of choosing Soviet players.

Even so, when you look at the unimpressive numbers put up by the Isles’ second overall pick and the numbers put up by the number 53 pick --Nicklas Lidström-- you can’t help be feel the Isles messed up big time.

As for Chyzowski, perhaps going to an emerging team like the Red Wings would have given him a chance to shine among some generational players.

15 Patrik Štefan (1999 - 1st Pick)

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Should Have Been: 27th Pick - New Jersey Devils

One can’t help but wonder if Patrik Štefan’s notoriety would be lessened if he wasn’t the Thrashers' first ever pick. But he was, and as such was the talisman for the franchise. And that right there gives you a good idea of why that franchise failed. A total of 188 points in 455 games is a respectable return for a third or fourth round pick, but not first overall. Presumably, the Thrashers would have much preferred to have the second or third pick --the Sedin twins-- but the twins refused to play on separate teams and it took some expert wheeling and dealing from Canucks’ GM Brian Burke to get the Swedes together in Vancouver.

Štefan was eventually traded to the Stars in 2006. Sadly for Štefan, his time in Dallas is best remembered for a truly hilarious empty-net miss. Had Štefan been picked 27th overall, after Martin Havlat, his name probably wouldn’t generate uproarious laughter as it does now. Not to mention going to the Devils of the late 90s on a team full of veterans would have been a great experience for Stefan.

14 Rick DiPietro (2000 - 1st Pick)

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Should Have Been: 30th Pick - St. Louis Blues

Another high goaltender draft pick by a New York team that backfired. This time it was the New York Islanders and it was the first overall pick. Rick DiPietro had a good junior career for Boston University and played amazingly well for USA at the World Junior Championship, so analysts figured he’d be drafted high. But ahead of Dany Heatley and Marian Gaborik? That’s a big move. And the Islanders made it. But let’s all be honest; DiPietro going first overall was not as big a mistake as the bafflingly enormous contract the Islanders signed him to in 2006. A 15-year, $67.5 million contract.

The deal was groundbreaking and served as a template for general managers to “front load” contracts and circumvent the spirit of the salary cap. Unfortunately for the Isles, DiPietro suffered a concussion a year later and injuries would continuously plague him, preventing him from ever playing a full season and forcing an early retirement. Had DiPietro been picked 30th, behind Red Wings’ defenceman Niklas Kronwall, nobody would criticize the Isles today. DiPietro also would have gone to a team that's been far more steady over the last 15 years in the St. Louis Blues. 

13 Alexandre Daigle (1993 - 1st Pick)

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Should Have Been: 24th overall - Chicago Blackhawks

Put on your oven mitts because here comes a hot take: Alexandre Daigle was not as bad a draft pick as he’s made out to be. Ask any hockey fan to name a draft bust, and most will probably blurt out Daigle’s name first. But come on, he’s not the worst. He scored 327 points in 616 career NHL games; that’s more than a point every other game. So he’s not the worst. He was a terrible number one pick, though. He never notched more than 51 points in a season and only scored 20 goals or more in four seasons. The Senators would have much rather had Chris Pronger or Paul Kariya, but we all make mistakes.

Had Daigle been drafted 24th overall, after guys like Jason Arnott, Saku Koivu, and Todd Bertuzzi, he would have had much less pressure and we’d be kinder to him today. Going to a team like the Blackhawks also would have given Daigle a better chance to thrive alongside Jeremy Roenick, Chris Chelios and Ed Belfour. Ottawa still had expansion team talent, so obviously Chicago would have been a much better situation for Daigle.

12 Gilbert Brulé (2005 - 6th Pick)

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Should Have Been: 105th Pick - Phoenix Coyotes

Now, 95 points in 299 career games is not what you expect from a 6th overall center. What’s worse, Brulé never scored more than 17 goals in a season. The 2005 draft was a difficult one to prepare for because of the league-wide lottery for places, that was held on the back of the locked-out 2004-05 season. Everybody knew who was going number one (Sidney Crosby) but beyond that, teams didn’t have that much time to prepare for who would pick where.

But Columbus should have done better than Brulé. Sure, Crosby, Bobby Ryan, and Carey Price were already taken, but the Blue Jackets could have had Anze Kopitar, Kris Letang, or Jonathan Quick, among others. Ultimately, if you switch Brulé with the 105th pick --Keith Yandle-- the draft looks much better. 

11 Daniel Tkaczuk (1997 - 6th Pick)

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Should Have Been: 156th Pick - Buffalo Sabres

Another center who was drafted sixth overall that didn’t quite pan out. The baffling thing about Daniel Tkaczuk is that the Canadian only played 19 NHL games, but he scored 11 points. That’s not bad, so it’s difficult to understand why he didn’t get more chances. What’s more, all those games came for Calgary in the 2000-01 season. He had a promising junior career with the Barrie Colts and led team Canada in scoring at the 1999 World Junior Championships.

That is why the Flames drafted him sixth overall, when it turns out they would have been much better off choosing Scott Hannan, Daniel Cleary, or Marian Hossa. Heck, the 156th pick would have been much better; Brian Campbell. After bumming around the AHL, Tkaczuk moved to Europe, finishing his career with the Nottingham Panthers in England. Yeah.

Going to the Sabres, an emerging team at the time, in a mid-round would have put less pressure on Tkaczuk and would have given him a greater chance to succeed.

10 Brian Lawton (1983 - 1st Pick)

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Should Have Been: 199th Pick - Chicago Blackhawks

Brian Lawton was the Alexandre Daigle of the 1980s. Only moreso. He was the first, and until Auston Matthews in 2016, the only U.S.-born player drafted first overall. Drafted by the Minnesota North Stars, Lawton recorded 266 points in 483 games, numbers that were somewhat inflated by playing in the hectic, free-flowing, offensively-minded 1980s. Lawton only ever broke the 20-goal barrier once in his career and was not the franchise forward the struggling North Stars needed. A fact that became increasingly frustrating as Pat LaFontaine, Steve Yzerman, and Cam Neely --all drafted later in the same round-- grew to become franchise forwards for their respective teams.

The 1983 draft was an odd one with several teams taking punts on already established Soviet players. A few, such as Sergei Makarov and Viacheslov Fetisov, would later come over to the NHL and play very well. But most, like legendary Soviet goaltender Vladislav Tretiak, never would make the move. However, it’s another iconic goalie that the North Stars should have chosen. The 199th pick: Dominik Hasek.

9 Alexander Svitov (2001 - 3rd Pick)

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Should Have Been: 95th Pick - Philadelphia Flyers

There are a lot of Russians on this list. It’s hard to know why. Maybe because the style of play in Europe is generally less physical than in North America. And many Europeans, especially Russians, don’t grow up idolizing NHL teams and players. Russia has its own league which is at a fairly high standard, so when things get tough in the NHL, many Russians opt to simply go home. That’s what Alexander Svitov chose to do in 2007. He left behind him an NHL career with 37 points in 179 games; a career that did nothing to dispel the stereotype of some Russian players being lazy.

To be fair to Tampa, Svitov was a highly touted youngster, being the youngest player to skate in the Russian Elite League. But if given a do-over, I’m sure the Lightning would much rather have had Mikko Koivu, Ales Hemsky, or Jason Pominville. Or how about the 95th overall pick, Patrick Sharp?

Going at no.95 for Svitov would have placed him in Philly, a team that typically produces many productive forwards. Then again, with his work rate, it probably wouldn't have worked out anywhere for Svitov.

8 Pavel Brendl (1999 - 4th Pick)

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Should Have Been: 210th Pick - Detroit Red Wings

I hope Pavel Brendl sends Patrik Štefan a Christmas card every year, because he owes a lot to him. If not for Štefan taking all the heat for being a terrible first overall pick in 1999, people might notice Brendl, the fourth overall pick, was truly awful. Brendl scored 22 points in 78 career NHL games, none of which were for the Rangers who drafted him. Brendl was an atypical bust because, unlike many Europeans, Brendl played junior in Canada. Brendl was a star for the Calgary Hitmen of the WHL, so he should have been used to the North American game. But it never clicked for Brendl in the NHL and he’s played in Europe since 2006. The 1999 draft makes a lot more sense if you switch Brendl with one of the most famous draft steals of all time; the the Red Wings’ 210th pick, Henrik Zetterberg.

If there was any team that could have salvaged something out of Brendl it would have been the Wings.

7 Jason Bonsignore (1994 - 4th Pick)

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Should Have Been: 133rd Pick - Ottawa Senators

In 1994, the Edmonton Oilers drafted their future captain and franchise forward, Ryan Smyth, sixth overall. What most people don’t remember is that Smyth was the Oilers’ second pick that year. They had traded to acquire the Winnipeg Jets’ first round pick, which was the fourth overall pick. With that pick they selected American center Jason Bonsignore, but they might as well have picked a bag of hockey pucks. Better still, they could have chosen Jeff O’Neil, Jose Theodore, or Patrik Elias, who were all picked later on in the draft. But no, they settled on Bonsignore, who would go on to record an unremarkable 16 points in 79 career NHL games.

Bonsignore played his final NHL game in the 1998-1999 season for Tampa Bay. He ended his career in 2008 in the ECHL with the Trenton Devils. The 1994 draft makes a lot more sense if you switch Bonsignore with the 133rd pick, Daniel Alfredsson.

6 Hugh Jessiman (2003 - 12th Pick)

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Should Have Been: 64th Pick - Detroit Red Wings

Poor Hugh Jessiman. Yes, you expect the 12th overall pick to play more than two NHL games. But it’s not the rarest thing in the world for a 12th pick to be a bust; it happens. But when it happens amidst perhaps the strongest draft year ever, people tend to notice. Many people would argue that the 2003 draft was the most talented selection of players ever, especially the first round. So when the New York Rangers saw a bunch of the other players from that year leading their teams in scoring and winning trophies just a few short years later, they must have been cursing themselves for picking the American winger Hugh Jessiman.

Indeed, the only other first round pick from 2003 you could say was a miss was the last pick of the round: St. Louis’s Shawn Belle. But even Belle played 20 NHL games. For the longest time, Jessiman had the dubious distinction of being the only player from the 2003 first round to not have played an NHL game. That all changed in 2011 when Jessiman finally suited up for the Florida Panthers. So he got there in the end. But I’m sure the Rangers wish they got the 65th pick instead, Jimmy Howard.

Similar to the reasoning for Brendl going to the Wings, Detroit would have provided a better chance for Jessiman to develop.

5 Nikita Filatov (2008 - 6th Pick)

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Should Have Been: 93rd Pick - Washington Capitals

Will the Columbus Blue Jackets ever learn? Three years after picking Gilbert Brulé, Columbus picked another forward with the sixth pick. But this time it was different...it was worse. It was worse because not only did Nikita Filatov suck, he was a pain in the ass, too. The BJs were well within their rights to pick Filatov, as the Russian winger was the top-ranked European skater according to the NHL Central Scouting Bureau. But Filatov was a headache from the very beginning. The president of Russia’s Kontinental Hockey League claimed that Columbus owed CSKA Moscow $1.5 million just for signing Filatov. After that was sorted out, Filatov could finally play, but he only ever played 58 NHL games, notching a paltry 14 points. What’s more is that he got annoyed with Columbus not playing him and he demanded a transfer back to CSKA Moscow. He would do the same thing years later to the Ottawa Senators and he’s played in the KHL since 2012.

In hockey, you can get away with being underwhelming for a while. You can get away with being a diva for a while. But you can’t be both. Filatov would have been better as the 93rd pick and Columbus should have picked Braden Holtby instead. Going to Washington would have placed Filatov with Ovechkin. That would have certainly been a more humbling experience for Filatov and playing alongside Ovie could have gotten the most out of him.

4 Daniel Doré (1988 - 5th Pick)

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Should Have Been: 129th Pick - Quebec Nordiques

When you read this list entry, you probably said, “Daniel Doré? Who is that?”. And you’d be right to say so. The French-Canadian only played 17 NHL games, all with the Nordiques, scoring five points. Doré is a stark contrast to the calibre of players the Nordiques would draft in the following three years, all number one picks: Mats Sundin, Owen Nolan, and Eric Lindros (though Lindros would pose his own problems). Doré, unfortunately, was not one one-hundredth of the players those guys were. His selection is made all the more maddening because of the names picked shortly after him: Jeremy Roenick, Rod Brind’Amour, and Teemu Selanne. But you can’t even argue that Doré should have gone in their place.

He belongs more around the 129th pick, where the Nordiques picked the already established Soviet star Valeri Kamensky, who would eventually move to the NHL in 1991. Something noteworthy about Doré: he didn’t end his career in Europe, the AHL, or even the ECHL, but rather playing roller hockey in Roller Hockey International.

3 Scott Scissons (1990 - 6th Pick)

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Should Have Been: 245th Pick - Winnipeg Jets

Judging from this list, both New York teams suck at drafting. And now we’re really into the dregs. If anybody knows of the players this far down the list it’s solely because of their status as draft failures. 1990 was known as one of the strongest draft classes ever, but the New York Islanders never got that memo. Instead they got the Canadian center Scott Scissons, as well as a lifetime of regret. Scissons would only ever play two regular season NHL games and one playoff game. He bummed around the International Hockey League (which doesn’t even exist anymore) before retiring in his early twenties, possibly due to injury problems. Who could the Isles have had instead? How about Darryl Sydor? Or Derian Hatcher? Keith Tkachuk? Or maybe Martin Brodeur? A better slot for Scissons would have been the eighth-last pick, after Sergei Nemchinov.

The 26-year old Soviet player would go on to have a solid NHL career and be among the first Russians to win a Stanley Cup with the Isles’ crosstown rivals, the Rangers, in 1994.

2 Alexandre Volchkov (1996 - 4th Pick)

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Should Have Been: 240th Pick - Colorado Avalanche

If Svitov and Filatov were draft failures because they didn’t try enough, Alexandre Volchkov is a failure because he didn’t try at all. The Russian winger only ever played three NHL games, doing nothing in any of them. To be fair to the Capitals, 1996 wasn’t a vintage year for draft picks. Even so, nearly anybody would have been a better fit for Washington than the human dumpster fire that was Volchkov. Marco Sturm, Daniel Briere, and Zdeno Chara all would have been a thousand times better.

Volchkov would play most of his career in Eastern Europe and Russia, ending it in 2011 in Kazakhstan. You’d have to go down to the last two picks that year, after 239th selection Sami Salo, to find a suitably anonymous spot for the inconsequential Volchkov.

If anything, maybe Volchkov would have been more motivated if he went to the defending champion Colorado Avalance, but even that's a stretch.

1 Ray Martyniuk (1970 - 5th Pick)

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Should Have Been: Never

The early days of the draft were not as refined as they are today. Teams were still figuring things out; it was not the fine-tuned science it would later become. Given that there are still draft failures today, you can imagine how many there were back then. But Ray Martyniuk stands above the rest. I suppose the Montreal Canadiens were still figuring out this whole draft thing. It had only been around for seven years and the Habs preferred the old system, when they could just buy an entire junior league to get the rights to Jean Beliveau.

What stings most about Ray Martyniuk is not that the four players drafted above him were all future all-stars. It’s not that Montreal could have had Darryl Sittler, Bill Clement, or Billy Smith instead. It’s that Martyniuk was actually nicknamed “The Can’t Miss Kid”. Well, guess what? He missed. He missed by a mile. The Canadian goaltender never played a single NHL game. Not one. He should never have been drafted.

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