We’ve already looked into what has happened in the recent past when teams trade a top pick for established veteran talent. The results weren’t great.
It’s worth noting again that none of the trades referenced in that article included a team knowingly giving up a top-five pick in the salary cap era, which is key with the Blackhawks sitting at No. 4. It’s pretty rare that a such a pick is traded at all, much less for an established player as the central piece. However, rare doesn’t mean never, but those times usually involved swapping picks rather than players. So we should also take a look at those instances, once again using the rough timeline of the last 30 years of NHL history.
1998: No. 1 overall pick from San Jose to Tampa for the No. 2 overall pick, Bryan Marchment and David Shaw
This one remains kind of incredible in retrospect, because the San Jose Sharks gave up a shot at Vincent Lecavalier and they ultimately ended up (after another trade down, see below) with Brad Stuart, a perfectly solid defenseman who had a long NHL career but was never remotely franchise-changing. Additionally, Marchment was a decent player, although more known for his fighting (313 penalty minutes with the Hawks in 1992-93!). Shaw was a body but, again, neither was worth that top pick.
Meanwhile, Lecavalier became the centerpiece of a Stanley Cup-winning core for the Tampa Bay Lightning and spent years as one of the league’s premier offensive centers.
1998: No. 2 overall pick and a 1998 third-round pick from San Jose to Nashville for the No. 3 overall pick and the No. 29 overall pick
Again, the Sharks added a late first-round puck by moving down to third, selecting Stuart at No. 3 and using the later pick on Jonathan Cheechoo. The strategy of quantity over quality is absolutely viable, but typically not in the top-10 of a draft. And it didn’t work out well for San Jose: Cheechoo had one very good season –scored 56 goals and won the Rocket Richard Trophy in 2005-06 (largely because he spent most of his life attached to Joe Thornton) — but it was an outlier. He then ended up having double hernia surgery two years later and never recovered.
Again, not remotely worth missing out on Lecavalier.
1999: The Sedin Sweepstakes
This was a mess that involved multiple top picks being exchanged, but it had only one winner: Vancouver, the team targeting the best players available in Henrik and Daniel Sedin. The gist of this ordeal was:
- Tampa Bay originally held the first overall pick and somehow emerged from all the maneuvering with basically nothing meaningful to show for it long term.
- Atlanta originally owned the second overall pick, traded up to No. 1, and ended up selecting Patrik Stefan, who turned into a fairly underwhelming player and certainly not one worthy of a top pick.
- Chicago was involved too, originally holding the fourth overall pick but trading it for Bryan McCabe (who was a Blackhawks for only one season) and a 2000 first round pick (11th overall, used to select Pavel Vorobyev who played less than 60 NHL games).
- Meanwhile, both teams passed on the Sedin twins, which was questioned at the time and looks outright catastrophic in hindsight.
If anything, all of this is really an example how important it can be to take the best player(s) available at the top of the draft whenever possible rather than chasing draft or asset capital.
Ben Kuzma: Hard to replicate Burke’s power of persuasion that secured Sedins https://t.co/qCJePPGyI8 pic.twitter.com/BT6Jyiqhs7
— The Province (@theprovince) June 15, 2019
2002: No. 1 overall from Florida to Columbus for the No. 3 overall pick and the conditional right to swap 2003 first-round picks
Columbus traded up to select Rick Nash, while Florida settled for Jay Bouwmeester at No. 3 overall. Now, Bouwmeester was a good NHL defenseman who played forever and eventually won a Cup with St. Louis, but his success obviously wasn’t with the team giving up the top-five pick. Nash was also clearly the more impactful player overall and became the face of the Blue Jackets franchise for years, even if the team also didn’t accomplish much with him at the helm.
Neither trade tree ultimately didn’t transformed the organizations long-term, either. Bouwmeester’s dies out just one trade later, while Nash’s after a few more trades not worth a mention here.
2003: No. 1 overall pick from Florida to Pittsburgh for the No. 3 overall pick, a second-round pick, and Mikael Samuelsson
Pittsburgh had their hearts set on Marc-Andre Fleury and, because Carolina was reportedly prepared to take him second overall, the Penguins opted to move up from third to first to snag the goalie. The Panthers ended up with Nathan Horton, who was a decent enough player but peaked at 62 points while Pittsburgh got a franchise goalie who backstopped a Cup winning team. Samuelsson had a lengthy NHL career but combining the accolades of him and Horton still fall well shy of Fleury.
In this case, the team moving up within the top-five was the winner — an option that might actually be the best for the Blackhawks this season, too (more on that below).
2004: No. 4 overall pick from Columbus to Carolina for the No. 8 overall pick and a 2004 second-round pick
Carolina did get the better value, though it was short-lived in term of immediate impact. They moved up to fourth overall to select Andrew Ladd, who was a useful lower line forward during their 2006 Cup winning season.But Ladd was only with the Hurricanes for three seasons before being traded to the Blackhawks in exchange for Tuomo Ruutu. Ladd eventually broke out in Chicago and won another Stanley Cup there in 2010. Ruutu was mostly fine for Carolina over seven seasons, but injuries frequently limited him and he ultimately settled in more as a solid middle-six player than a major difference-maker.
Columbus Blue moved down to eighth and selected Alexandre Picard, who never made it in the NHL, and the second-round pick was a nobody too.
THIS DATE IN 2003: The @penguins select Marc-Andre Fleury with the first overall pick in the #NHLDraft. Since then, he has won the #StanleyCup three times and currently owns the third most regular-season wins in NHL history with 492. #NHLStats pic.twitter.com/99PbE3g0M4
— NHL Public Relations (@NHLPR) June 21, 2021
2008: No. 5 overall pick from the New York Islanders to Toronto for the No. 7 overall pick, a 2008 third-round pick and a 2009 second-round pick
This one could help set the market for what the Blackhawks may need to give up in order to move up from that No. 4 spot. Toronto gave up two additional two picks to move up two spots, selecting Luke Schenn with that No. 5 pick. That trade didn’t work out so well for the Leafs in the short-term, though, as Schenn struggled while playing for some subpar Toronto teams in the late-2000s and early-2010s. Schenn’s biggest contribution to the Leafs may have been helping bring James van Riemsdyk to town, which happened in a 2012 trade.
And that’s the last time an NHL team has traded into the top-five of a draft or moved up within the top-five spots, exempting trades like the famed Phil Kessel one that resulted in Boston receiving a No. 2 selection that wasn’t known to be a top-five pick at the time of the deal (mentioned in the other article).
As noted earlier in the day, trading a top pick for established veteran talent doesn’t seem like the best road forward for the Blackhawks due to the historical trends of those trades not yielding a worthwhile return along with the lack of desirable talent available via trade thanks to the soaring salary cap.
What feels slightly more possible — and plausible — is the Blackhawks exploring a trade up from No. 4 rather than moving it for an established NHL player. It hasn’t happened in 18 years, of course, but never say never. And if they go that route, the most obvious trade partner is San Jose.
With the Maple Leafs winning the lottery and securing the top pick of the 2026 NHL Draft, TSN Director of Scouting Craig Button joins James Duthie to share his mock draft for how he sees the first 16 picks playing out. Thoughts? 🤔 #NHLDraft pic.twitter.com/wuGQw6Qqjg
— TSN (@TSN_Sports) May 6, 2026
San Jose already has a loaded pool of young, talented forwards, which has led to some speculation that they could prioritize taking a defenseman. It’s still hard to imagine the Sharks passing on McKenna or Stenberg if they’re sitting there at No. 2, though. Team needs matter, but elite talent usually wins out at the very top of the draft, and Sharks GM Mike Grier is nothing if not a logical man.
But if that’s truly the case, it opens the door for Chicago to at least make a serious phone call about jumping up the board. The Blackhawks have a surplus of draft capital over the next few years, along with a growing logjam of young defensemen, both in the NHL and among their prospects. If Davidson decides there’s a meaningful tier break after the top two or three players in this class, packaging the fourth overall pick with additional assets to move up probably makes more sense strategically — and historically, in terms of some success — than cashing the pick in for a veteran NHL player.
It’s almost certain Toronto isn’t going to look a gift horse in the mouth and move from the No. 1 pick, though who knows what newly appointed Leafs GM John Chayka will do considering his questionable past related to the draft. He was actually responsible for at least one of the poor trades detailed earlier.
John Chayka says he can honestly claim not to know who the #leafs will draft at No. 1: "We haven't had scouting meetings yet. Second day on the job."
— Chris Johnston (@reporterchris) May 5, 2026
The safest, sanest option is probably that the Blackhawks simply holding onto the No. 4 pick and selecting another top prospect themselves. Maybe they get lucky and Stenberg somehow drops to No. 4, but that feels like the sequel to last year’s “Michael Misa could slip” hope that was never realized. Perhaps a player like Caleb Malhotra, Chase Reid, or someone else emerges as the perfect complement to the Blackhawks’ prospect pool. But the issue there is that the player selected won’t have an immediate NHL impact. Rebuilds do take patience, but it’s become harder and harder to practice that patience as more seasons pile up with Chicago still toiling near the bottom of the league standings.
There will be plenty of debate in the coming weeks about what the Blackhawks should do with the No. 4 pick. That decision will need to be the result of a careful weighing of this team’s short-term need for improvement at the NHL level against the long-term value that comes with holding on to the premium asset that is a top draft pick.