May 26: When drafting a player out of North America or any European country with a transfer agreement, a team acquires exclusive negotiating rights for a set amount of time. Each year on June 1, a long list of players see those rights expire and become unrestricted free agents (or choose to re-enter the draft, depending on specific circumstances).

CapFriendly has compiled a complete list for the deadline in just a few days. Some players listed below have already signed overseas; others will have agreements announced soon after their current rights expire.

Anaheim Ducks

Sean Tschigeri (130th overall, 2021)

Arizona Coyotes

Axel Bergkvist (200th overall, 2019)
Manix Landry (139th overall, 2021)
Emil Martinsen Lilleberg (107th overall, 2021)
Valentin Nussbaumer (207th overall, 2019)

Boston Bruins

Matias Mantykivi (185th overall, 2019)

Calgary Flames

Jack Beck (168th overall, 2021)
Lucas Feuk (116th overall, 2019)
Cole Huckins (77th overall, 2021)
Cole Jordan (141st overall, 2021)
Cameron Whynot (89th overall, 2021)

Carolina Hurricanes

Bryce Montgomery (170th overall, 2021)
Robert Orr (136th overall, 2021)

Columbus Blue Jackets

Eric Hjorth (104th overall, 2019)

Dallas Stars

Jacob Holmes (143rd overall, 2021)
Conner Roulette (111th overall, 2021)
Samuel Sjölund (111th overall, 2019)

Detroit Red Wings

Gustav Berglund (177th overall, 2019)
Albert Grewe (66th overall, 2019)
Oscar Plandowski (155th overall, 2021)
Pasquale Zito (166th overall, 2021)

Edmonton Oilers

Patrik Puistola (73rd overall, 2019)

Florida Panthers

Braden Hache (210th overall, 2021)

Los Angeles Kings

Lukas Parik (87th overall, 2019)

Montreal Canadiens

Frederik Nissen Dichow (138th overall, 2019)
Joe Vrbetic (214th overall, 2021)

New Jersey Devils

Nikola Pasic (189th overall, 2019)

New York Rangers

Leevi Aaltonen (130th overall, 2019)

Ottawa Senators

Carson Latimer (123rd overall, 2021)
Ben Roger (49th overall, 2021)
Chandler Romeo (202nd overall, 2021)

Pittsburgh Penguins

Santeri Airola (211th overall, 2019)
Ryan McCleary (194th overall, 2021)

San Jose Sharks

Benjamin Gaudreau (81st overall, 2021)
Liam Gilmartin (167th overall, 2021)
Max McCue (156th overall, 2021)

St. Louis Blues

Tyson Galloway (145th overall, 2021)

Tampa Bay Lightning

Cameron MacDonald (160th overall, 2021)

Toronto Maple Leafs

Kalle Loponen (204th overall, 2019)
Josh Pillar (127th overall, 2019)

Vancouver Canucks

Arvid Costmar (215th overall, 2019)
Connor Lockhart (178th overall, 2021)

Washington Capitals

Martin Hugo Has (153rd overall, 2019)
Dru Krebs (176th overall, 2021)

12:04 PM: With tomorrow’s deadline approaching for many expiring draft rights, a few last-minute dealings may be made. The Edmonton Oilers have done just that, acquiring Jayden Grubbe from the New York Rangers in exchange for a 2023 fifth-round pick. If not signed by tomorrow evening, Grubbe’s rights would no longer belong to the Oilers.

The fact that they made this trade suggests that an entry-level contract will soon follow, though it has not yet been announced. Grubbe, 20, was a third-round pick of the Rangers in 2021 but still hasn’t taken the jump to elite production in the junior level, despite his NHL size.

In 2021-22 he had just 14 goals and 35 points in 68 games, and while this year was better—18 goals and 67 points in 64 games—it may still not have been enough to make the Rangers interested in offering him a deal.

That, or perhaps the Alberta native didn’t see a future for himself in the Rangers organization. He’ll now get a chance to sign closer to home, and start his professional career with the Oilers minor league system.

Standing 6’3″, Grubbe has shown some flashes, but has a long way to go before making an impact at the NHL level. The fact that the Rangers landed a fifth-round pick for him is rather impressive, given how close they were to losing him for nothing.

From the Oilers perspective, this may have been their best chance at landing the young forward. Should Grubbe’s rights expire, he could re-enter the draft. If they were willing to spend a fifth (or higher) on him anyway, it makes sense to do the deal ahead of tomorrow’s deadline.

Grubbe was a third-round pick by New York in 2021 (65th overall) following an injury- and pandemic-shortened 2020-21 campaign that limited him to just five games with Red Deer of the WHL.  The hope was that as a big center – he stands 6’3 – he’d slowly develop into an impactful middleman and quality centers with size are typically hard to come by.

However, Grubbe didn’t exactly light things up last season, notching 14 goals and 21 assists in 68 games.  For a drafted player in his post-draft season, those numbers are a bit on the low side.  To his credit, Grubbe nearly doubled those totals this year, tallying 18 goals and 49 assists to finish second on the Rebels in scoring.  He has been quite productive in the playoffs so far, notching a goal and nine assists in their five-game victory over Calgary.

With the Rangers notifying teams early of their intentions, they’re hoping that there will be interest from a few teams that will enable them to pick up a late-round pick to flip his rights.  It wouldn’t be the best return on a high third-round selection but at this point, anything they can get is better than losing Grubbe’s rights for nothing.  If no one picks up and signs Grubbe, he will re-enter the draft in June.