May 16, 2026; Montreal, Quebec, CAN; Buffalo Sabres defenseman Bowen Byram (4) defends the puck against Montreal Canadiens center Alex Newhook (15) during the third period in game six of the second round of the 2026 Stanley Cup Playoffs at Bell Centre. Mandatory Credit: David Kirouac-Imagn Images
Not long ago, the Carolina Hurricanes won the Stanley Cup, and the NHL offseason began. Since then, several big moves have been made. That includes a wild few trades taking place on Tuesday, June 23. A good portion of the expected or predicted blockbusters have already taken place, and free agency technically hasn’t even begun yet.
While there are still moves to be made that will likely shock the NHL, Tuesday will likely remain the biggest day of the offseason. Each trade made could be argued as the biggest of the year, and they all happened on one day.
Blackhawks trade NHL picks for Bowen Byram
The Buffalo Sabres knew they likely weren’t keeping star defenseman Bowen Byram, who had dreams of being a top defenseman for a team. So, they sent Byram and forward Jordan Greenway to the Chicago Blackhawks.
In exchange, the Sabres, who became a playoff darling in 2025-26, received the number four overall pick and the number 45 overall pick in this year’s draft. That’s a major haul for the Sabres and a huge price to pay for an admittedly good player in Byram. The Blackhawks are finally going for it and pairing Byram with a young core that includes Connor Bedard and Frank Nazar.
Jordan Kyrou finally gets dealt
It has long been rumored that Jordan Kyrou would be dealt, and on Tuesday, it finally happened. The St. Louis Blues finally sent the star forward to the Washington Capitals. In exchange, the Capitals sent pending RFA Connor McMichael, forward prospect Milton Gastrin, and the 16th pick in the upcoming draft.
Kyrou has five years left at $8.125 million AAV, and the Blues are not paying any of it, so they escape his contract entirely. The star player had to waive his no-trade clause in order to get dealt to the Capitals. The Caps finally added another top-six NHL forward to the mix. After missing the postseason in what could be Alexander Ovechkin’s final season, the Capitals needed to make a move.
Senators flip recently-acquired pick
The Ottawa Senators recently made the move of the offseason by finally parting ways with Brady Tkachuk. They sent him to play with his brother on the Florida Panthers. Part of the package was the number nine overall pick this year, and they’ve already flipped it.
The San Jose Sharks traded William Eklund, winger prospect Kasper Halttunen, and the rights to prospect Brandon Svoboda to Ottawa for the pick. The Senators instantly added more talent in the wake of Tkachuk’s exit.
Simon Nemec blockbuster NHL trade
If not for the Bowen Byram trade, this Simon Nemec deal might’ve been the biggest NHL move of the day. Nemec is a former number two overall pick, and he’s been very good for the New Jersey Devils. Now, he’s with the Calgary Flames in a stunner. It’s a huge deal for both sides, though, and it could open the Devils up to a fire sale.
Nemec is headed to Calgary along with forward Maxim Tsyplakov. The Flames are sending prospect defenseman Etienne Morin, a 2026 second-round pick (via New York Rangers), a 2027 first-round pick (via Vegas Golden Knights), and a 2028 first-round pick (via Colorado Avalanche).
Zachary Roberts has written in the sports industry for over four years. He's covered the Carolina Panthers, Charlotte Hornets, Seattle Seahawks, and wider coverage of the NFL, pro golf, NHL, MLB, and NBA. He has worked with ComicBook, Sportskeeda, The Sporting News, and the On SI Network. In his free time, Zachary loves playing video games, watching movies, or reading books.
More From Playboy
Sports
Lionel Messi Spearheads Historic, Controversial Comeback for Argentina The World Cup has delivered yet again, with defending champions Argentina and Lionel Messi completing a two-goal comeback in a matter of 13 minutes. Not long after that, his Argentinian teammates scored in stoppage time to put the reigning FIFA World Cup winners (2022) in front for the first time all day, sending Egypt to a shocking, frustrating exit from the Round of 16.
Sports
Shohei Ohtani Rebounds From Ugly Start, Confusion with Catcher The Minnesota Twins were giving L.A. Dodgers' Shohei Ohtani all he could handle, but good pitchers adjust. That's exactly what Ohtani did after allowing three runs in two innings. He adjusted.
Sports
Perfect USMNT Run in World Cup Ends in Meaningless Bout The USMNT lost to Turkiye, but what was really important ahead of a game that mattered for literally nothing was finding out which subs could be relied on for big minutes.
