San Jose Sharks make waves as Kiefer Sherwood inks a five-year, $28.75 million extension—Mike Greer’s biggest contract yet. Is Sherwood the missing piece for San Jose’s renewed offense, or will the lengthy commitment haunt the team down the line?
JD Young spotlights Sherwood’s remarkable journey and gritty play, tying in last night’s clutch performance and the vital role he brings to the middle six. The deep dive covers the contract’s unique structure—including trade protections and cap hit breakdowns—while assessing the risks and rewards as Sherwood enters his thirties. Key topics feature Grier’s strategic exit ramps, the implications for future Sharks roster moves, and whether San Jose’s shift toward bigger deals signals a new era. Is this a stepping stone toward playoff contention, or a gamble that could backfire?
Timestamps:
00:00 Sharks Sign Kiefer Sherwood
06:03 Sharks’ Future with Sherwood
08:51 Breaking Down Sherwood’s Contract
12:05 Sherwood’s Contract Flexibility Explained
13:59 Sharks’ Manageable Sherwood Contract
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18 Comments
Sure, he’ll be 36… And two time Stanley Cup winner #hope
Hopefully he keeps playing with his hair on fire and help the team be a legitimate cup contender in the next few seasons.
It’s a character/catalyst move. Grier doesn’t have to do a bunch of moves like this. His impact on the young players could be immeasurable.
We all talked about, should he be traded, the other day. Some of us thought he should go. Lol. What a difference a day makes. Well, we have him now! I'm hoping for the best and cheering him on ! ..are we genius or moron?
JD was argued FOR this contract and term two videos ago. What changed?!
After last night’s game the first thing I thought was there is no way he’s getting traded now. Wish it was a 2-3 year deal but this deal isn’t the end of the world and rentals like Sherwood would cost us 1st and/or 2nds each year in the future as realistic contenders around the deadline
Was waiting on this episode to hear your thoughts about keeping Sherwood around for 5 years
I can’t say that I like this. Last night’s game not withstanding he hasn’t exactly fit well. I get that it’s small sample size, but I mean, if you can’t accidentally get on the score sheet skating on a line with Smith and Celebrini for four games…
And this guy at an AAV of $5.75 mil — I have a bad feeling that this contract is gonna look Vlassic levels of bad in 2 years. Sherwood is the type of player that I could easily see being a 20 point per year third line guy by the time he’s 33, which is useful, but not $5.75 million AAV useful. At least it is front loaded and is structured in a way that we can prolly pay a team to take the cap hit off our books if the contract is the albatross I expect it will be 3 years from now.
Also, he’s not a defenseman. Woof.
not thrilled at the cost/duration, but hope to be proven wrong
Bobby McMann is in a similar situation, I wonder if this signing/extension if other teams will change their tune on him now…
Spot on JD. I don’t mind this Contract as much as others do. Pretty sure other than Mac, he’s going to be a Fan Favorite. You’re right the last couple of Years might not be great, but it won’t be as bad as some of the Contracts Grier inherited and had to get rid of.
Ideally a 2 year deal would be perfect but a 13 team ntc and him being locked at 5.7 for 3 years remaining at that point for a solid third liner…. This should be a reasonably easy trade piece at that point.
What this says to me is that either Mario is gone after the year or Eklund will be gone before or when his contract is up. With Celebrini and Smith extensions on the horizon and Misa and Dickinson coming the year after it's gonna be a struggle to upgrade the defense or goaltending in a few years. I know the cap is going up, but also will player demands with the cap rising.
Obviously, Goodrow's contract is off the books after next year and Toffoli the year after. You figure chasing a top dman will cost you possibly 8-11 million a year. That's why I see Eklund being used as part of a package for a dman who's contract numbers are already known. Not that I dislike Eklund. He's a fine complimentary player, those are replaceable. I feel with the Sharks being smallish down the middle that Mike may prefer bigger wingers when they are ready to be true contenders.
Once they stopped trying to keep him on the first line his game turned around. He doesn't have the speed to keep up with Macklin and Smith. He is a perfect fit with Wennberg. The Sharks need a guy who will take the body early and often but has the ability to score as well.
So they don't see much of a future in Bysted and Musty
Sherwood is 30 and will be 31 this month.
And it is a five year deal.
So we have the player at 31-32, 32-33, 33-34, 34-35 and 35-36 years old.
I'm not sure that he's worth 5.75 million next season.
Toffoli has slowed down and Sherwood is going to be quite a bit older in the latter years of it.
I'm 99% sure that we end up buying out the contract in year 3, 4 or 5.
There are progressively more teams we can try to trade him too, as the contract ages.
But by the time he's slowing down, no one is going to want the player.
So even with total freedom to trade him anywhere, no one is going to want him and we'll be stuck.
It seems expensive for a 3rd line winger.
I mean, would you be happy to extend Toffoli at 5.75m AAV, for another four seasons after his contract expires?
On the topic of money and to put things in the real world context, Sherwood is making about 10 x what someone will make in their lives over the next 5 years. That’s about 450 working years for the average person for 5 years of work. Those numbers are just crazy. Congratulations Sherwood, you’ve made a multigenerational changing deal!
I'm excited and I'm trying so hard to test JD's point about the future here, but I do agree. And I'm also gonna let future me worry about it.