Where Does June 23 Rank in the Busiest Days in NHL History?

The best part about the offseason is that anything can happen at any time. In the NHL, there are a couple of sanctioned days such as the draft (June 26-27 this year) and free agency (typically July 1). But there are no guarantees that the biggest moves happen those days, and they often don’t.

Everyone in the hockey world was reminded of that Tuesday afternoon and evening as first-round picks and high-end players started changing hands rapidly. Usually, reports of a potential expansion team would dominate headlines, but that almost became an afterthought by the time the biggest bombshell dropped.

Between about 3:30 and 9:30 p.m. Eastern Time, an offseason already off to a dramatic start after Monday’s Brady Tkachuk trade became much, much crazier. Here’s a recap of everything that went down, and how it stacks up with some of the wilder days of off-ice action.

Deals, Deals, and More Deals

Forget chronological order; the most seismic swap was the last one of the day. The last time an NHL team knowingly traded a top-five pick was June 20, 2008, when the Toronto Maple Leafs moved from seventh to ninth in a deal with the Nashville Predators before trading up with the New York Islanders to select Luke Schenn fifth overall.

Bowen Byram is a fourth-overall selection, and like Schenn, he was drafted with a pick his team traded for. That was when the Ottawa Senators had to give the Colorado Avalanche their 2019 first-rounder to fulfill the Matt Duchene trade after exercising their conditional right to retain their 2018 first-rounder (also fourth overall). That pick became Brady Tkachuk, who the Senators had since then until all of two days ago.

Tangent aside, Byram is a solid player, a better one than his now-former Buffalo Sabres teammate Schenn. His career-high 42 points this season nearly double the best output for Schenn, and he played a key role in the Colorado Avalanche’s 2022 Stanley Cup championship, averaging over 19 minutes a night in the playoffs. His usage was even higher this spring, playing over 22 minutes a game in Buffalo’s first playoff run since 2011.

But the fourth-overall pick is supposed to be an elite player. Byram is good, but not truly that, and yet the Chicago Blackhawks decided to give up that selection to acquire him and forward Jordan Greenway. Not only that, but the Sabres also acquired a second-rounder (45th overall on Friday) and 25-year-old Louis Crevier.

Chicago general manager (GM) Kyle Davidson understandably wants to get his team out of the basement as Connor Bedard’s entry-level contract enters its final season. Byram is the best defender here and now on a Blackhawks backend that includes 2024 second-overall pick Artyom Levshunov, 2022 seventh-overall pick Kevin Korchinski and 2022 25th-overall pick Sam Rinzel.

That’s about as much draft pedigree as any defense in the league, but Chicago will have to put it all together. Oh, and they’ll need to sign Byram to an extension soon, as he’s set to hit free agency in 2027. We’ll save that discussion for another day, although that’s almost as important as the deal itself.

The last time any top-10 pick, period, was knowingly moved in advance was when the Vancouver Canucks acquired the ninth choice in 2014 for Cory Schneider, which they used on future captain Bo Horvat. The Byram trade wasn’t even the first one of the day to break that threshold, though, nor was Byram the highest drafted player moved. To begin the trade avalanche, the Senators moved the ninth-overall pick that was part of the Tkachuk trade to the San Jose Sharks for a package headlined by William Eklund.

Eklund was supposed to be part of the forward core developing in San Jose, a playmaking winger who’s hovered around 40 assists the last two seasons, exceeding 50 points both times. Prospects Kasper Halttunen and Brandon Svoboda could make an impact down the road, but make no mistake, this trade is about Eklund plugging a hole in the Senators’ top-six.

If anything, it seemed like the Sharks might be moving a top-10 pick instead of adding another, with their GM Mike Grier, saying he’d received “legitimate offers” amidst serious discussions with five teams for the second-overall pick just hours before making this move.

A selection that high hasn’t been traded since newly inducted Hockey Hall of Famer Brian Burke’s wheelings and dealings to snag Daniel and Henrik Sedin second and third overall, respectively, in 1999. Maybe that will change later this week. But this was still a vital trade for the Senators to at least somewhat replenish their offense if they hope to stay competitive in a loaded Atlantic Division.

The highest drafted player on the move Tuesday was Simon Nemec, as Sunny Mehta’s first trade as New Jersey Devils GM as a blockbuster. The Devils have a lot of talent on their backend, and with Nemec in need of a new deal as a restricted free agent that would require his new GM making a massive commitment to an imperfect-but-talented player, New Jersey decided to reallocate their resources.

Interestingly, the Calgary Flames were the team to acquire him, given Calgary’s most valuable player is also a right-handed offensive defenseman, Zayne Parekh. But the Flames need high-end talent everywhere, and adding a skilled right-shot defender is never a bad idea. It sure cost a pretty penny; the first-round picks they acquired from the Vegas Golden Knights for Rasmus Andersson and from the Avalanche for Nazem Kadri.

Those were the moves that defined their 2026 Trade Deadline, and now they’re bundled together in one big package. There are a couple of other pieces to the deal; the Flames get Maxim Tsyplakov to aid their bottom-six, and New Jersey adds the 35th-overall pick this year and prospect Etienne Morin. It’s a big haul for Mehta, but you never draft someone second overall expecting to move on from them in four years. We’ll see if the Devils regret it.

It’s crazy that the Jordan Kyrou trade almost slips through the cracks here. You could easily argue Kyrou was the best player moved today; his 75 points in 2021-22 and 378 career points, all with the St. Louis Blues, are easily the most of Byram, Nemec, Eklund and Connor McMichael, who was part of the package for him. His offensive numbers were down in 2025-26, but he’s earned Frank J. Selke Trophy votes each of the last two seasons (rare for a winger) and had 70 points as recently as 2024-25.

If Alex Ovechkin returns for a 22nd NHL season, it’s easy to see the pass-first Kyrou and him having a field day in the offensive zone and giving the Capitals potentially one last playoff run for the Great Eight. Still, the Blues made out solid. McMichael is a center capable of scoring 20 goals, and he’s not alone. Milton Gästrin is also listed as a center and was taken 37th-overall a year ago.

But if there’s a team to look out for future fireworks from, keep an eye on the Blues. Adding the 16th-overall pick gives them a whopping four first-rounders this year, including three in a six-pick range between 10 and 16. That’s about as concentrated as we’ve seen a team have three first-rounders since the Boston Bruins’ trio of consecutive picks in 2015. That’s tied for the second-most ever, one behind the 1974 Montréal Canadiens in the peak of the Sam Pollock era. New GM Alex Steen — let’s see what you’ve got.

How Does It Compare?

The trade deadline is “supposed” to be the day when the biggest trades are made. On this year’s deadline day (March 6), three first-round picks changed hands. On June 23 alone, five first-rounders were shuffled around, ranging from the fourth-overall pick that will be made on Friday to a pick that could be made as late as 2029.

The universal pick for craziest off-ice day in NHL history, especially if you’re excluding draft and deadline days, has been June 30, 2016. In about half an hour, Steven Stamkos re-signed with the Tampa Bay Lightning for eight years and $68 million, P.K. Subban was traded straight up for Shea Weber, and Taylor Hall was traded one-for-one for Adam Larsson.

Does June 23, 2026, pass that? It’s in question. On one hand, no first-round picks were traded on that day almost a decade ago, let alone two top-10 picks or one as high as fourth overall. But that day involved headlines for two former first-overall picks (Stamkos and Hall), a three-time Norris Trophy runner-up in Weber, and a Norris winner in Subban. None of the players dealt in the last 24 hours can match that pedigree, and they very well never will.

With hindsight, we know that day was a huge deal. Stamkos won two Stanley Cups on that contract with the Lightning and played for another (even if he missed almost the entire playoff run the first time due to injury). Subban and Weber both reached the Stanley Cup Final with their new teams, with P.K. adding a Norris nomination and an EA Sports NHL cover appearance while with the Nashville Predators. Hall won the Hart Trophy in 2018 and just captured his first Stanley Cup, although linking the latter to the Larsson trade is a bit of a stretch.

The website NHL Trade Tracker has a page dedicated to some of the sport’s biggest trades. There are only a few days with multiple deals. July 23, 2021, was the roster freeze deadline before the Seattle Kraken expansion draft and saw the Columbus Blue Jackets send Seth Jones to Chicago in a deal involving three first-round picks (two going to Columbus, one to Chicago).

The Vancouver Canucks also gave up a first and second to acquire Oliver Ekman-Larsson and Conor Garland from the Arizona Coyotes, a deal that didn’t work out as they intended to say the least (Ekman-Larsson was bought out after just two seasons). There was other activity that day, with the Blues acquiring Pavel Buchnevich for a cheap price and the Flyers paying top dollar for Rasmus Ristolainen.

A pair of trades from day one of the 2015 NHL Draft also make it, both involving the Bruins loading up on futures. They dealt Dougie Hamilton to the Flames for a first and two seconds and Milan Lucic to the Los Angeles Kings for a first plus Colin Miller and Martin Jones (who they immediately flipped to the Sharks, setting the stage for San Jose’s run to the Final the next season).

Other than three team trades, those are the only days with multiple trades under that category. That’s not a definitive list, of course. And the date June 23 has seen big trades before, like when the Los Angeles Kings acquired franchise icon Marcel Dionne from the Detroit Red Wings or Flyers moved Mike Richards to the Kings and Jeff Carter to the Blue Jackets on the same day in 2011.

Are There More Trades to Come?

Definitely. Probably not this much on one day, though, even with the draft and free agency always fulcrum points on the NHL’s summer calendar.

As 23 minutes of madness shows, the impact of days like this will last a long time. The Sharks feel on the verge of building a dynasty with two more top-10 picks set to join Macklin Celebrini. Nemec and Parekh could one day lead the Flames back to contention. Eklund, rightly or wrongly, will be viewed as Tkachuk’s replacement with the Senators and receive all the attention that comes with that. And there may be even more pressure on Byram to justify one of the most valuable draft picks ever traded.

For a while, the NHL has been viewed as a relatively unspectacular league in terms of off-ice action. The late 2010s-early 2020s blockbusters that became common in the NBA felt like a different planet from hockey operated. That sure doesn’t feel like the case right now.