It’s trade-deadline season in the NHL, which means GMs around the league are working the phones in an attempt to make a move. Some of the deals being discussed will come to fruition, while most will never go anywhere. As much as we may rip on these guys for not getting deals done, the truth is that it really is tough to find a fit in today’s NHL.
But there’s one trick that can make closing out a deal a little easier. When in doubt, why not throw in a draft pick to balance the scales?
It makes sense, and most deals that get done these days have at least a pick or two thrown in somewhere. But every now and then, those picks can come back to haunt you, as we’ll see in these 10 trades that didn’t seem like big deals at the time, but ended up indirectly involving a future superstar.
For this list, we’re not worried about cases where a team traded up on the draft floor to target a specific player. We’re looking at situations where a team acquired a pick months or even years in advance, only to have an eventual star fall into their lap.
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So tread carefully, NHL GMs — you never know when that pick you throw in to make a deal work will come back to haunt you.
1. THE TRADE: On Nov. 4, 1983, the Winnipeg Jets acquire defenceman Robert Picard from the Montreal Canadiens in exchange for a third round pick at the 1984 draft
The rationale: The Jets were trying to build a roster that could do something other than lose in the first round of the playoffs every year, and needed some depth on the blueline. Picard was a solid-enough player, and a third-round pick seemed like a fair price.
But the pick turned into: On draft day, the Canadiens traded up to get picks in the first and second round, which they used on Shane Corson and Stephane Richer. But the deal cost them multiple picks as well as Rick Wamsley, so they needed to replenish their goaltending depth.
They used the Jets’ third-round pick to do it, grabbing a skinny kid from the QMJHL named Patrick Roy.
The epilogue: Picard was fine in two seasons as a Jet before being dealt to the Nordiques for Mario Marois.
2. THE TRADE: On the eve of the 1978-79 season opener, the Los Angeles Kings trade their first-round pick in the 1979 draft to the Boston Bruins for goalie Ron Grahame
The rationale: The Kings needed a goaltender after Rogie Vachon had signed with Detroit in free agency. Vachon had been an all-star and he’d appeared in 70 games the year before, so his departure left a huge void. With backup Gary Simmons also out of the picture, the Kings needed somebody to fill the starter’s job, and apparently didn’t trust prospect Mario Lessard to handle the load.
They turned to the Bruins and Grahame, who’d just put up an excellent half-season and, at 28 years old, seemed like a guy who could be their starter for years to come.
But the pick turned into: The pick ended up being eighth overall in what’s now viewed as perhaps the greatest draft ever, and the Bruins used it to pick Ray Bourque.
The epilogue: As it turns out, the Kings didn’t even need a goalie after all; Lessard played well enough to beat out Grahame for the starter’s job, and held it for four years. Just over two years after trading a first round pick for him, the Kings sent Grahame to the Nordiques for cash in 1980.
3. THE TRADE: On July 2, 2001, the Philadelphia Flyers trade Daymond Langkow to the Phoenix Coyotes for a second-round pick and a first rounder in either 2002 or 2003
The rationale: Langkow was a solid two-way forward, and at 24 he appeared to have plenty of good years ahead of him. He’d yet to crack the 20-goal mark, but the Coyotes figured he had room to blossom. After three straight years of finishing with 90 points, they wanted to move up the standings, and paid accordingly.
But the pick turned into: The Coyotes had a good year in 2001–02, posting 95 points, and their first-rounder ended up being the 19th-overall pick. Flyers’ GM Bobby Clarke decided to roll the dice and wait another year, hoping the Coyotes would regress and he’d wind up with a better pick in the loaded 2003 draft.
It paid off, as the Coyotes collapsed to 78 points. Their pick ended up being the 11th-overall choice. The Flyers used it to select Jeff Carter.
The epilogue: Langkow did break out with the Coyotes, putting up 27 goals and 62 points in 2001–02 and having three productive seasons in the desert before being traded to Calgary. But it’s fair to say that Carter, or any of several other future all-stars taken in that 2003 first round, would have been a better longterm fit for the Coyotes.
4. THE TRADE: As part of the complicated quasi-expansion process that welcomed four WHA teams to the NHL, the Edmonton Oilers agreed not to take Paul Shmyr from the Minnesota North Stars in exchange for a fourth-round pick
The rationale: The entire process was a weird one in 1979, with teams claiming players from the WHA newcomers and the WHA teams turning around and claiming them back. Shmyr had actually been an Oiler the previous season, but Minnesota held his NHL rights and wanted him in the lineup. So two months before the entry draft, they sent a pick to the Oilers to make it happen.
But the pick turned into: The Oilers had already hit home runs on each of their first two picks, choosing Kevin Lowe in the first and Mark Messier in the third (after acquiring the pick in a draft-day trade with, yes, those same North Stars).
When the fourth round rolled around, the Oilers used their North Stars pick from the Shmyr deal to choose a speedy winger from the University of Denver: Glenn Anderson.
The epilogue: Schmyr played two seasons in Minnesota, never topping 20 points, before leaving as a free agent in 1981.
5. THE TRADE: At the 2006 trade deadline, the Oilers acquire Sergei Samsonov from Boston in exchange for Marty Reasoner, Yan Stastny and a second-round pick
The rationale: The Oilers were loading up for a post-season run. At the time, that might have seemed optimistic — they were right on the playoff bubble — but they ended up going all the way to the final.
But the pick turned into: The Bruins used that second to pick a hulking WHL prospect named Milan Lucic.
The epilogue: Samsonov did provide an offensive spark, chipping in with 16 points in 19 games in the regular season and then another 15 points in 24 playoff games. And of course, the Oilers eventually got Lucic anyway, so it all worked out fine.
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6. THE TRADE: Any time the Toronto Maple Leafs trade a first-round pick a year or more before the draft
The rationale: Draft schmaft!
But the pick turned into: Take your pick. In 1989, the Maple Leafs acquired Tom Kurvers for a 1991 first-rounder, which ended up turning into Scott Niedermayer. In 1996, they shipped a 1997 first as part of the package to reacquire Wendel Clark, and that one ended up being Roberto Luongo. And in 2009, of course, it was a pair of firsts in the Phil Kessel deal that turned into Tyler Seguin and Dougie Hamilton.
The epilogue: The Maple Leafs learned their lesson and will never do that again, he told himself, not really believing it.
7. THE TRADE: In another one of those weird deals related to the WHA expansion, the Chicago Blackhawks allowed the Quebec Nordiques to keep Real Cloutier in exchange for Quebec’s first-round pick in the 1980 draft
The rationale: Cloutier was a legitimate star in the WHA; in its final season, he’d led the league in goals with an eye-popping 75 in 77 games. He’d been the league’s leading point scorer in two of the previous three years, and at just 23 years old he was easily the Nordiques’ best player.
Here’s where it gets a little weird. Under the rules, the Nordiques had the right to protect Cloutier from being claimed by the team that held his NHL rights, in this case the Blackhawks. But they chose to work out a trade with Chicago instead, freeing up their protection slots for other players. It ended up being costly.
But the pick turned into: All the WHA teams struggled in their first year in the NHL, including the Nordiques. They finished with just 61 points, good for 19th in a 21-team league, and handed the third-overall pick to the Blackhawks.
That pick ended up being Denis Savard. When the Canadiens surprisingly passed over Savard with the first-overall pick, Chicago ended up having arguably the best prospect in the draft fall into their lap.
The epilogue: Cloutier continued his goal-scoring success, potting 42 in his first NHL season. But injuries slowed him down after that, and he was traded to Buffalo in 1983.
8. THE TRADE: On Feb. 25, 2004, the Nashville Predators sent Timo Helbling to the Tampa Bay Lightning in exchange for an eighth-round pick
The rationale: Helbling was a marginal prospect who only went on to appear in nine games in Tampa, recording a single point. But still, it was an eighth-round pick. What are the odds that it would turn out to be anyone good?
But the pick turned into: A massive Finnish goalie named Pekka Rinne.
The epilogue: Helbling also played two games with the Capitals, ending his big-league career with 11 games played and just that one point. Rinne wouldn’t establish himself as a regular NHLer until 2008, but since then he’s been pretty good.
9. THE TRADE: At the 1999 trade deadline, the Panthers sent Rhett Warrener and a fifth-round pick to the Buffalo Sabres for Mike Wilson
The rationale: Unlike the list of buyer/seller deals we see at the deadline these days, this was a deal involving two similar players. Warrener and Wilson both played defence, they were both solid in their own end, and they were roughly the same age. But apparently they weren’t quite viewed as equals, and the Panthers had to toss in a fifth to get the deal done.
But the pick turned into: With the 138th-overall selection in the 1999 draft, the Sabres took Michigan State goalie Ryan Miller.
The epilogue: Miller obviously turned out to be a fantastic pick, eventually taking over the Sabres’ job after Dominik Hasek’s departure and holding it down for the better part of a decade. But you could also argue that the Sabres came out ahead in the Wilson/Warrener swap. Wilson battled injuries in Florida and left as a free agent in 2001, while Warrener was part of the Sabres’ run to the Cup final in 1999 and stuck around until 2003, when he was traded to Calgary in a deal that brought back Chris Drury.
10. THE TRADE: Pretty much every move Montreal Canadiens GM Sam Pollock made in the late-’60s and early-’70s
Remember how hockey pools in the mid-’80s would make Wayne Gretzky ineligible, because he was just so dominant? For the same reason, we’re grouping all of Pollock’s into one entry. There’s really no other choice. The man was just too smart and too far ahead of his time, and he used the future-pick-accumulation strategy on so many of his fellow GMs that most of this list could just be Canadiens picks from the Pollock era.
The rationale: None. Never trade with Sam Pollock. Seriously, 1970s GMs, how many times did you have to watch one of your colleague get robbed blind before you realized this guy was playing 3D chess and the rest of you were shoving checker pieces up your nose?
But the picks turned out into: Guy Lafleur, Guy Carbonneau, Steve Shutt, (takes deep breath), Bob Gainey, Mario Tremblay (another breath) and Larry Robinson. All of those Habs legends were drafted with picks that Pollock acquired in exchange for names like Ernie Hicke, Gerry Desjardins and Bob Murdoch.
In some cases, the future pick came as many as four years out from the original deal. When it came to taking his fellow GMs to the cleaners, Pollock was willing to be patient.
And it was almost even worse for the NHL — in a 1972 trade, Pollock fleeced the Golden Seals for their first-round pick in the following year’s draft. As expected, the Seals were terrible. But the expansion Islanders were slightly worse, so Pollock just missed out on the first-overall pick. If you think the 1970s Habs dynasty was good, imagine them with Denis Potvin. It nearly happened.
The epilogue: Four straight Stanley Cups from 1976–79, and a gold standard for NHL GMs that’s yet to be matched.