3 Worst Signings From Day 1 of NHL Free Agency

Day one of the 2026 NHL Free Agent period has come and gone. The free agent class wasn’t looked upon fondly leading up to July 1st, and some big names, like John Carlson, received big-time money. With the salary cap exploding, I thought that we’d see some huge contracts handed out, but some of the numbers still shocked me. When judging the worst deals, I looked at a mix of how it’ll help the team now, in the future and what it did to the rest of the cap situation. The list isn’t in any particular order, but these are my three worst contracts handed out this Canada Day.

Jacob Trouba

I was not a fan of what San Jose Sharks general manager (GM) Mike Greer did at all today. I can’t believe the Darnell Nurse trade, but I also can’t believe he gave Jacob Trouba this deal. At 32 years old, Trouba signed in San Jose for four years with an annual average value (AAV) of $8.25 million.

Trouba had a little bit of a resurgence in Anaheim after being moved away from the New York Rangers. Through 81 games, he recorded 10 goals, which was only the third time in his career that he achieved that, and he tacked on 25 assists to go with it.

While the point totals started to climb back to respectable numbers, and he provides the physicality that teams love to have on the backend, there are serious concerns about Trouba’s game. His defensive numbers weren’t great, basically breaking even during his minutes, which was a huge upgrade from the last three seasons. Trouba is also a poor skater at his older age, which I can see being a big scheme mismatch on a young, quick Sharks roster.

Today leaves the Sharks with $14 million in cap space after day one. It is a lot of space, but when you pair this contract with the Nurse move, I’m having trouble seeing what Grier is trying to do with the defense corps. I find this signing not just a bad contract, but an odd fit.

Sergei Bobrovsky

This is the biggest bet that was made today, and I don’t think it’s particularly close. Buying large, I’ve loved what Toronto Maple Leafs GM John Chayka has done, but this gamble really scares me. Sergei Bobrovsky wasn’t retained by the Florida Panthers after reportedly asking for a long-term deal. Now, he hits the open market, signing a three-year deal with an AAV of $7 million with the Maple Leafs.

Bobrovsky was obviously a huge part of the three straight Stanley Cup appearances, where they won back-to-back Cups, but last season was one to forget. Through 52 games played, he recorded an .877 save percentage (SV%), -23.66 goals saved above average (GSAA), and -1.75 goals saved above expected (GSAx).

Now the Panthers were badly beaten up with injuries which made it a much more difficult year but his play was undeniably bad. On top of his play, the Leafs are a worse defensive team than Florida was at its best. Even with the reconstruction of the bottom-six and the blue line under construction, I don’t think the rosters are comparable.

The age is something that is obviously a red flag, but by all accounts, Bobrovsky does a great job managing his body. What I worry about is that after the Dennis Hildeby trade, the Leafs are now relying on Anthony Stolarz, whose career high in games is 34, and a 38-year-old goaltender who could probably benefit from some load management.

This signing is incredibly boom-or-bust, and I hope I end up being wrong, but I’m concerned about the lack of a safety net with Hildeby being moved out.

Vincent Desharnais

The Washington Capitals have done a lot of good this offseason, but giving Vincent Desharnais a four-year deal with an AAV of $4.2 million was not that. The 30-year-old 6-foot-7 defenseman had a good defensive year in San Jose and will be a physical presence on the third pair for Washington. While I think there are qualities of his game that are good, I just can’t believe that is the price and term you have to pay for a third-pairing defenseman.

If you’re giving a third-pair defenseman four years, that is supposed to bring the AAV down, but it feels like the Capitals still paid a premium for a third-pair, stay-at-home defenseman.

People are justifying most of these contracts with the cap going up, but we’re still not in an environment where you need to be paying a bottom-pair defenseman over $4 million. Bottom-pair defenseman should also be fairly replaceable, so I don’t quite understand the urgency to lock Desharnais up.

July 1st is one of my favourite days on the NHL calendar. With all the movement we saw this year in signings and trades, it didn’t disappoint.