Five years ago, the Edmonton Oilers struck it rich at the draft lottery — again.
Deputy commissioner Bill Daly held up their logo, signalling their unofficial victory in the Connor McDavid sweepstakes and prompting an unforgettably awkward and widely overanalyzed reaction from the soon-to-be NHL superstar.
The Oilers had just an 11.5 per cent chance of going home with the top pick in the 2015 NHL Draft, their fourth No. 1 selection in the previous six years (2015, 2012, 2011 and 2010).
Sometimes the ping-pong balls go your way.
But sometimes they don’t.
The Buffalo Sabres’ lottery-best odds resulted in the No. 2 pick and a chance to grab Jack Eichel, who’s not a bad consolation prize but certainly isn’t McDavid.
Comb through the past of the event, which dates back to 1995, and there are plenty of teams who were favoured or shunned by chance.
Ahead of the first phase of the NHL’s modified draft lottery Friday, we took a look at the biggest winners and losers in its history.
Edmonton Oilers — 2015
Back to the 2015 lottery, I don’t think it can be overstated how big of a win it was for the Oilers organization — even if they’ve made just one post-season appearance since drafting McDavid, though they’ll make another should the NHL return from its pandemic pause.
By jumping to the top spot, with the third-best odds, Edmonton secured a franchise-defining player.
During his time in the NHL, the 23-year-old pivot leads the league in Goals Above Replacement, according to Evolving Hockey (108.5), well ahead of Mark Stone at No. 2 (96.2), points (469 in 351 games) and owns a Hart Trophy and two Ted Lindsay Awards. He’s achieved all this despite suffering a career-threatening injury in his left knee that ended his 2018-19 campaign, and a broken clavicle in his rookie season.
The Oilers’ win was the Sabres’ loss — no doubt about it. The sheer drop off from McDavid to Eichel is debatably enough to qualify the Sabres as one of the biggest lottery losers in history.
Eichel is a star, and was mounting a dark horse bid for the Hart this season, but McDavid has vastly outproduced him since joining the league. Eichel’s GAR is a tad more than half that of McDavid’s (56.8) and he is 24th in total scoring over that span with 337 points in 354 games.
Great numbers, but they don’t touch McDavid’s.
Pittsburgh Penguins — 2005
The Penguins were certainly due for some luck, and they got it at likely the strangest draft lottery in history.
Amid struggles on and off the ice, the Penguins were thrown a lifesaver in the form of the No. 1 pick in the 2005 NHL Draft.
Coming out of a lockout that wiped out the entire 2004-05 season, the NHL had no standings to use for the lottery and opted to assign teams into three groups based on playoff appearances in the previous three seasons and how many first overall picks a team had in the past four drafts.
Based on the system, the Penguins were one of four clubs to get the maximum three lottery balls (out of 48 total), while 10 had two and 16 had one.
Despite having among the best odds to win, that amounted to a just 6.25 per cent chance as each team had a shot at Sidney Crosby — the most highly coveted prospect in the game since Mario Lemieux.
But everything came up Millhouse for the Penguins on July 22, 2005.
Pittsburgh landed the No. 1 pick, paving the way for its third, fourth and fifth Stanley Cup wins (2008–09, 2015–16, 2016–17) led by Crosby, who has been unquestionably the greatest player of his generation.
Since 2005, Crosby’s 1263 points in 984 games are second to only Alex Ovechkin’s 1278 in 1152, even though much of his prime was hampered by injuries. With two Art Ross Trophies, two Harts, three Ted Lindsays, two Richard Trophies and two Conn Smythes, he’s by far the most accomplished selection in a rather weak ’05 draft, which also produced Bobby Ryan (No. 2), Carey Price (No. 5), Anze Kopitar (No. 11) and Kris Letang (No. 62).
Chicago Blackhawks — 2007
The Blackhawks had a franchise-defining win a few years before earning their first Stanley Cup since 1961, but it didn’t come on the ice. With the fifth-best odds to end up with the top pick, Chicago leaped up the draft board and the right to pick Patrick Kane, who became one of the most prolific scorers of his time.
This year ties directly to one of the biggest losers in NHL Draft Lottery history as well, so a little more on this one below.
Bonus — Taylor Hall
The self-proclaimed “lottery-ball specialist” has been on five teams that have won the top prize. Twice with the New Jersey Devils (Hischier, 2017 and Jack Hughes, 2019) and three times with the Oilers (Ryan Nugent-Hopkins, 2011, Nail Yakupov, 2012, and McDavid, 2015), in addition to being the No. 1 overall pick himself by Edmonton in 2010.
Hall is confident his record will stand — never tell him the odds.
Honourable mentions: The Colorado Avalanche going from second to first and snagging Nathan MacKinnon in the 2013 NHL Draft. The Winnipeg Jets jumping from sixth to second to land Finnish sniper Patrik Laine in 2016.
Philadelphia Flyers — 2007
It’s hard to imagine a tougher year for the Flyers.
Eight games into the 2006-07 season, with the team off to a 1-6-1 start, general manager Bobby Clarke resigned and head coach Ken Hitchcock was fired. But the shakeup made no difference as the Flyers finished 22–48–12, giving them the most losses in franchise history and the NHL mark for the biggest one-year drop in standings from 101 points to 56.
And how were they rewarded for compiling the league’s worst record?
By dropping to the No. 2 spot in the draft lottery and missing out on one of the greatest American hockey players of all time — Patrick Kane.
The Chicago Blackhawks, meanwhile, catapulted up to the first choice — despite having the fifth-best chances at 8.1 per cent — and paired Kane with Jonathan Toews to form the core of a modern dynasty that won three Cups in six years. It’s one of the biggest lottery wins in history, from the other side of the picture.
The Flyers ended up taking James van Riemsdyk, a fine player in his own right. But he’s not the owner of an Art Ross, Calder, Ted Lindsay, Hart and Conn Smythe award, nor is he the third-most prolific point-getter since entering the league in 2007-08.
As an added twist of the knife three years later, it was Kane who silenced the Flyers’ crowd as he scored the Blackhawks’ Stanley Cup-winning, OT goal in the 2010 Final.
New York Islanders — 2001
A year after surging from fifth to first at the lottery and using the top pick to take goalie Rick DiPietro over the likes of Dany Heatley and Marian Gaborik, the Islanders, and GM Mike Milbury, did themselves one better.
Having finished last in the regular-season standings with 52 points, the Islanders had the best shot at the top pick (25 per cent) and a chance to select a game-changer in Ilya Kovalchuk.
But the hockey gods chose to favour the Atlanta Thrashers (14.2 per cent odds) with No. 1 and give the Islanders the second choice. The Thrashers seized the chance to pair Kovalchuk with a fellow sniper in Heatley.
That stung but another future star in Jason Spezza was left for the taking.
It was the Islanders’ corresponding move that truly sealed their status as losers that summer. In what may be one of the worst trades in NHL history, New York sent No. 2, Zdeno Chara and Bill Muckalt to the Senators for Alexei Yashin. The Islanders promptly signed the Russian centreman to a gargantuan 10-year, $87.5-million contract that haunted the team’s books through 2014-15 following a 2007 buyout.
Would the Islanders have made the same trade had they won the top pick? We may never know. But what is clear is that Yashin failed to carry New York past the first round of the playoffs, while Kovalchuk, Spezza and Chara shined elsewhere.
Bonus — Pittsburgh Penguins (the fans) — 2004
Ok, before I get dragged in the comments, I’m aware the Penguins did pretty well for themselves at the 2004 lottery by coming away with Evgeni Malkin second overall.
But there’s no denying the Capitals — who finished third from the bottom — winning the lottery over the last-placed Penguins may have deprived fans of an opportunity to watch one of the greatest playmakers in NHL history line up alongside arguably the greatest goal scorers in NHL history. It’s like something out of an NHL 20 fantasy draft.
While Pittsburgh got Malkin — a future Hall of Famer who’s no second-fiddle to Crosby and was essential to the team’s most recent three Cups — Ovechkin, the top pick, is the league’s leading point-producer since the ’04-05 lockout and by far its most prolific goalscorer (he leads Crosby 706 to 462 in that category).
Ovechkin’s also got his name on nine Richard Trophies, three Ted Lindsays, three Harts, an Art Ross, a Conn Smythe and a Calder. Malkin, meanwhile, has 1076 points in 907 games since entering the league a year later — placing him fourth in points since the ’04-05 lockout — and is the owner of two Art Ross Trophies, a Hart, a Ted Lindsay, a Smythe and a Calder.
The Penguins weren’t really losers, neither were the fans who’ve been privileged to watch Geno and Sid the Kid tear it up in Pittsburgh. But c’mon, even the most diehard Penguins fans have to admit they would’ve loved to have seen what Ovechkin could’ve accomplished on Crosby’s flank.
Dishonourable mentions: The last-placed Atlanta Thrashers missing out on Rick Nash and picking oft-injured goalie Kari Lehtonen at No. 2 in the 2002 draft.
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