Top 10 worst draft-lottery losses

As draft-lottery consolation prizes go, Jack Eichel is looking like a pretty good one. John Crouch/Icon Sportswire

Connor McDavid's recent injury was a devastating blow to both his Calder chances and the Edmonton Oilers' already shaky playoff hopes. It also hit the pause button on his rookie rivalry with Jack Eichel, temporarily shutting down a storyline that figured to be one of the season's best. After all, those two players will be forever linked by hype, circumstance and, of course, those four ping-pong balls that determined their futures.

That would be the April draft lottery, one that saw the Oilers leap past the last-place Buffalo Sabres for the top overall pick. With McDavid ranked as the consensus No. 1, that moment felt like a brutal loss for the Sabres, a perception that was only reinforced by their own general manager. (Not everyone sees it that way; many Sabres fans insist they were just fine with getting either player all along. These people are crazy, but they'll burn my house down if I don't mention them.)

While McDavid's injury puts the Eichel comparison on hold, it does lead to a fun question: Which draft-lottery loss was the most painful in league history? Which last place team took the worst hit by dropping down to No. 2?

The NHL introduced the draft lottery in 1995. Not counting last year, that leaves us with an even 10 instances when a team has "lost" the lottery, which we'll define as the last-place team overall getting passed over for the top pick. (So we're not counting 1995, 1999 or 2011, when the winning team didn't move up to first.) With the benefit of some hindsight, we can look back at the teams involved, the eventual top pick and the player who fell to No. 2, and try to figure out which loss hurt the most.

We'll work our way down from best to worst. And we'll start in 1998, the first time the lottery ever resulted in the top pick changing hands, sort of.

No. 10: 1998

Last-place team: Tampa Bay Lightning

Lottery-winning team: San Jose Sharks, by virtue of owning the Florida Panthers' pick

First overall pick: Vincent Lecavalier

How much did it hurt?: This is the easiest call on the list, because it didn't hurt at all. Literally. It had no impact on anything, as you might already suspect if you're thinking, "Uh, I don't remember Lecavalier being drafted by the Sharks."

That's because the last-place Lightning went into the lottery with an insurance policy in their back pocket. At that year's deadline, they had traded Bryan Marchment and David Shaw to San Jose for Andrei Nazarov and convinced the Sharks to toss in a sweetener: the right to swap their first-round pick for the Panthers', which San Jose had acquired earlier in the season. With the Lightning well back of the Panthers in the standings, the swap option wouldn't matter. Unless Florida won the lottery.

They did, and the Lightning moved back up to first. The Sharks got the second pick, flipped it to Nashville (who took David Legwand) and ended up getting Brad Stuart third overall. And Lecavalier headed to Tampa Bay to become "the Michael Jordan of hockey."

No. 9: 2000

Last-place team: Atlanta Thrashers

Lottery-winning team: New York Islanders

First overall pick: Rick DiPietro

How much did it hurt?: A ton for the Islanders. It's not often that you can use the phrases "disastrous lottery win," but such was the Mike Milbury era. The Isles jumped from fifth to first and did a jig about it, then used the top pick on DiPietro. It's fair to say it didn't work out. Not only did DiPietro eventually get one of the worst contracts (and later one of the most expensive buyouts) in NHL history, but the Islanders made room for him by trading a young Roberto Luongo to Florida.

Meanwhile, the Thrashers dropped down to the second pick and wound up with Dany Heatley, who they probably would have taken anyway. And Atlanta even got some karmic payback against the Islanders the following year, which we'll get to farther down this list.

No. 8: 2003

Last-place team: Carolina Hurricanes

Lottery-winning team: Florida Panthers

First overall pick: Marc-Andre Fleury

How much did it hurt?: The 2003 draft is the best of the last few decades and might be the best of all time, so that eases the sting here. When guys such as Ryan Getzlaf, Zach Parise and Corey Perry are going in the second half of the first, and Patrice Bergeron and Shea Weber are dropping to later rounds, falling from No. 1 to No. 2 isn't all that bad.

That's especially true for the Hurricanes, who saw the Panthers leapfrog them and then trade the top pick to the Penguins, who picked Fleury. Carolina then took Eric Staal, who went on to help them win a Stanley Cup and is still the team's best player today.

No. 7: 2012

Last-place team: Columbus Blue Jackets

Lottery-winning team: Edmonton Oilers

First overall pick: Nail Yakupov

How much did it hurt?: This one's a bit of a moving target. Just a month or two ago, we might have described Yakupov as a bust, but a strong start to this season has improved his reputation. Either way, he wasn't the sure-thing top prospect in a 2012 draft that wasn't viewed as especially strong. With the Blue Jackets needing to restock their blue line, there's at least a chance that they would have picked Ryan Murray, even if they'd held on to the top spot, so this one didn't sting too much (even if their fans weren't very happy at the time).

No. 6: 2014

Last-place team: Buffalo Sabres

Lottery-winning team: Florida Panthers

First overall pick: Aaron Ekblad

How much did it hurt?: We're just one year removed from this one, so it's too early to declare a clear winner between Ekblad and the player the Sabres wound up with, Sam Reinhart. But it's fair to say Ekblad holds an edge so far, winning the Calder Trophy last season while Reinhart spent most of his time in junior hockey.

Would the Sabres have taken Ekblad? They said Reinhart was their guy all along, although that's what every team says. A blue-liner would have been a good fit for a Buffalo team already well-stocked up front, especially given that by this point they already seemed to be banking on McDavid or Eichel. Today, Ekblad probably helps this team more than Reinhart, but there's a long way to go on this one. And, hey, at least losing the 2014 lottery gave Sabres fans some valuable practice for next time.

No. 5: 2002

Last-place team: Atlanta Thrashers

Lottery-winning team: Florida Panthers

First overall pick: Rick Nash

How much did it hurt?: For the third time on our list, the Panthers win the lottery but see another team end up with the top pick. This time it was because they traded down with Columbus on draft day, dropping down to third and still getting the guy they wanted, Jay Bouwmeester. The Blue Jackets took Nash.

As for the Thrashers, while they missed out on Nash, they were already stacked at wing. They used the second overall pick on goalie Kari Lehtonen, and while Nash turned out to be the far better player, Atlanta might well have made the same choice even if they'd been selecting No. 1.

No. 4: 2013

Last-place team: Florida Panthers

Lottery-winning team: Colorado Avalanche

First overall pick: Nathan MacKinnon

How much did it hurt?: This one's a tough call, since the 2013 draft was a strange one. At the time the lottery was held, the consensus top pick was defenseman Seth Jones. In fact, some of the more conspiracy-minded fans found it odd that Jones' hometown Avalanche just happened to be the ones to win the right to take him.

But the Avs passed on Jones in favor of Nathan MacKinnon, and then the Panthers raised eyebrows by taking Aleksander Barkov at No. 2. (Jones dropped down to Nashville at No. 4.) Today, hindsight says MacKinnon or Jones would have been better choices, but it's too early to put much stock in that. The better question: Was Barkov the Panthers' guy all along? Or had they decided on picking a center and were banking on MacKinnon being there? We don't know, but common sense leans toward MacKinnon being the pick.

No. 3: 2004

Last-place team: Pittsburgh Penguins

Lottery-winning team: Washington Capitals

First overall pick: Alex Ovechkin

How much did it hurt?: Let's start with the obvious: This was a two-player draft, and the Penguins' pick at No. 2 was future Hall of Famer Evgeni Malkin. Pittsburgh isn't exactly sobbing here.

That being said, Ovechkin is by far the best non-McDavid prospect ever taken with a lottery-determined pick. And we were this close to seeing him play out his career with Sidney Crosby. That's almost unthinkable for a generation of fans who've watched the NHL desperately try to force a Crosby-Ovechkin rivalry, and if not for a wayward ping-pong ball, it would have happened.

And if the Penguins were going to miss out on the chance to draft the best winger of his generation, losing him to a rival and (eventual) division rival hurts. So even though Malkin was a more than adequate consolation prize, this one still rates highly.

No. 2: 2001

Last-place team: New York Islanders

Lottery-winning team: Atlanta Thrashers

First overall pick: Ilya Kovalchuk

How much did it hurt?: Remember that payback for 2000 we mentioned? Here it is, and it's a good one. One year after the Islanders leapfrogged the Thrashers, the reverse scenario played out. And unlike in 2000, there really is a franchise player waiting at the top of the draft, in Russian phenom Ilya Kovalchuk. The Thrashers happily picked him and paired him up with Heatley to form a two-headed monster that would score a ton of goals.

As for the Islanders, the good news was that the 2001 draft had a second potential franchise player available in Jason Spezza. The bad news was that Milbury was still the GM, so he traded the second pick to the Senators for Alexei Yashin. To make matter worse, the Isles also gave up Zdeno Chara in that deal. To make matters even worse, they also gave Yashin a massive contract that was amazingly still on their cap until last year. It's not easy to combine one of the worst trades in hockey history with one of its worst contracts, but that was the magic of the Mike Milbury era.

Do the Islanders still make the Yashin trade if they win the lottery and keep the No. 1 overall pick? We might never know, but Milbury seemed determined to land a veteran star for his young Islanders team. I'm betting they still make the deal, which keeps this lottery loss from top spot on our list.

No. 1: 2007

Last-place team: Philadelphia Flyers

Lottery-winning team: Chicago Blackhawks

First overall pick: Patrick Kane

How much did it hurt?: If you were going to script the most painful lottery loss possible, this would be it. Let's recap. The 2006-07 Flyers unexpectedly plunged from three straight 100-point seasons to a miserable 56-point season, the biggest single-season drop in league history. The GM quits, the coach is fired and the Flyers finish dead last by double-digits in the points column. But, hey, at least the draft featured one of the best American prospects of all time.

Then came the lottery, in which the Blackhawks jumped up from fifth to earn the top pick. They used that selection to take Kane, who already has a Calder, a Conn Smythe and three Cup rings. The Flyers settled for James van Riemsdyk, who developed slowly before being traded straight-up for Luke Schenn, who's spent much of this season as a healthy scratch. I'd call that a drop-off.

But it gets worse. Three years after the lottery, the Flyers had turned things around enough to make the Stanley Cup finals against those same Blackhawks. With a chance at the franchise's first championship in 35 years hanging in the balance, the two teams played a tight series that could have gone either way. And then this happened. I mean, that's downright cruel, even for Flyers fans. They lost a lottery, wound up with a much worse player and then saw the guy they missed out on score the Stanley Cup-winning goal in their own building. There's really no other choice for the top spot on this list.

Congratulations, Flyers, you're No. 1. (Unlike in 2007.)