The Toronto Maple Leafs have re-upped their last remaining restricted free agent of note, signing 24-year-old goaltender Dennis Hildeby to a three-year contract extension.

The 6-foot-7, 2022 fourth-round draft pick led all Toronto Marlies netminders in games played (30) in 2024-25 while also making six appearances for the Maple Leafs in his rookie NHL season.

After a stellar start to his AHL career in 2023-24, Hildeby stumbled through a difficult season. As the Leafs dealt with injuries to their NHL tandem, Hildeby did not appear ready for NHL minutes. When called up in 2024-25, Hildeby put up an .878 save percentage through his first six NHL games.

While the sizeable, athletic Hildeby won 16 of his 30 AHL games, he also saw his AHL save percentage drop to .908 this season.

Hildeby’s extension is unconventional and reflects his up-and-down North American professional career to this point. Hildeby’s deal is a two-way contract from 2025 to 2027, before it becomes a one-way contract in 2027-28. His contract has an AAV of $841,667.

There was a time in the 2023-24 season that Hildeby’s smooth transition to North American hockey made him look like a possible Maple Leafs goalie of the future. He was sixth among AHL rookie goalies that season with a .913 save percentage.

Yet his 2024-25 season was marred by a propensity to allow far too many goals for multiple games in a row. His confidence shot up and down, and his play was inconsistent as a result.

Hildeby was given the nod for the Marlies’ first playoff game this season. He allowed four goals on 31 shots in an overtime loss to the Cleveland Monsters. That the Marlies did not turn back to Hildeby for Game 2 was telling. The Marlies lost the best-of-three playoff series in two games.

Yet Hildeby is back. Does his extension suggest he can still become the Maple Leafs’ goalie of the future?

Behind the scenes, the Leafs sent Hildeby home this summer with a goal for him to attain: develop more of a hardened edge. The team sees him as an athletically gifted goalkeeper but one who, at times, can let bad goals and losses fester for too long. They’d like him to find more of his inner confidence. And if that lends to a little more nastiness on the ice — maybe Hildeby uses his impressive frame to take command of his goal and swat the pests away — then that’s even more of a plus.

The Leafs remain hopeful his athleticism drives him to the NHL. But the nature of his contract still could lead to multiple outcomes.

Both Hildeby and the Leafs know he’s not yet ready for anything close to full-time NHL duty now, and might not be in 2026 either. Being on a two-way deal suggests Hildeby will spend the majority of 2025 to 2027 commanding the Marlies’ net.  The Leafs have not signed a Matt Murray or Michael Hutchinson-type veteran goalie to fill the No. 3 hole. Hildeby should be given plenty of runway to develop his game through starts with the Marlies if that stays the case.

As of right now, there will be no other challenger for the third goalie spot in the Leafs organization. Artur Akhtyamov put up gaudy numbers to start last year with the Marlies, but his play leveled off as the season wore on. Still with just one North American season under his belt and with questions about his maturity and strength, Akhtyamov should be brought along slowly.

Vyacheslav Peksa remains in the last year of his entry-level contract. He will likely remain in the ECHL for most of the season.

All of which stands to benefit Hildeby.

Because Hildeby won’t have to pass through waivers, the two-way deal protects the Leafs against another team swooping in and taking a chance on Hildeby. Yet come 2027, Hildeby’s deal will transition into a one-way contract. By the start of the 2027-28 season, Hildeby will be 26. That season feels like a reasonable deadline for him to start putting up NHL-ready goaltending. To get there, Hildeby will have to improve his mental game as much as what he shows on the ice.

For now, Hildeby remains both an insurance option and a development project that may take a little longer than originally anticipated to find his NHL game.

(Photo: Claus Andersen / Getty Images)