Success is a funny thing in the NHL. You spend years begging for it, scraping the bottom of the standings to accumulate the draft capital necessary to build it, and praying to the lottery gods to bless it.
Then, when it finally arrives, it brings a headache.
For the first time in six years, the San Jose Sharks aren’t looking at mock drafts in December. They are firmly, undeniably in the hunt for a playoff spot. The Tank is getting loud again, and there is an undeniable buzz and excitement for all things teal in the Bay.
And with that comes a miserable, complicated, and ironically unenviable predicament for general manager Mike Grier.
The hardest part of any rebuild — much less one as scorched-earth comprehensive as the project Grier has overseen — isn’t starting it; it’s deciding when it is over.
While the Sharks still have immense room to grow, the true goal of this process wasn’t to pop champagne for the privilege of getting swept in the first round. The goal is winning multiple Stanley Cups.
Up until this point, that north star was always easy to follow. The organization didn’t have a “now” to balance against the goals of “later.”
They do now.
And let’s be specific about what that means: It means that Grier has some truly tough decisions on who is — or who is not — traded before the NHL’s deadline in March.
Because of the league’s obsession with mediocrity — sorry, they call it “parity” — we’re already seeing big deals being made. Everyone wants a leg up as early as possible.
This, folks, is a serious seller’s market.
And in a vacuum, a team in the Sharks’ position — middle of the pack, rising but flawed — should be selling high.
But we’re not in a vacuum, are we?
In fact, it might be most prudent for them to do the one thing that feels counterintuitive: keep the band together, keep the vibes high, keep pushing for the playoffs, and take the risk of losing good players to free agency when you re-open the roster in the summer.
The blueline is the specific area of focus, and it is a mess of contradictions.
Looking at the books, only Dmitry Orlov and Sam Dickinson are signed for next season. Everyone else is playing for a contract, be it in San Jose or somewhere else.
Again, in any prior Shark season under Grier, San Jose would have throwing plenty of chum into the trade waters.
And give Grier truth serum, and he’d probably tell you that back in September, he fully expected to be shopping — and selling — veteran defensemen John Klingberg and Nick Leddy in the coming weeks.
That was the script. Sign vets, rehabilitate their value, and flip them for more picks and young players.
Why else would the Sharks be carrying all these defensemen if they didn’t plan on moving a couple of them?
The problem? Macklin Celebrini and friends rewrote the script.
Leddy, picked up off waivers this summer, hasn’t played enough or well enough to create much of a market. His value is minimal, even in a league where GMs hoard defensemen like canned goods during an apocalypse.
Klingberg, on the other hand — pun intended — presents the real dilemma.
He has played up-and-down hockey, but he’s found some balance lately. And look at the stat sheet: He is fifth in the NHL in goals by a defenseman. He’s also that deeply coveted, right-handed blueline shot that quarterbacks a power play.
He could land a pretty sweet pick. There will be a market for Klingberg. There is a market for him.
The problem? Well, he’s a right-handed shot defenseman who has proven to be the only viable power-play quarterback, and he’s also a respected veteran leader in a room full of kids.
His value to a playoff contender is his value to the Sharks.
And the Sharks have no obvious replacement for him — no young whippersnapper in the pipeline ready for his moment. Sorry, but Dickinson isn’t that guy yet.
If Grier trades Klingberg for, say, a second-round pick and a prospect, he is effectively waving a white flag on the power play and — this doesn’t take much extrapolation — the playoff push.
The complications continue down the depth chart. Vincent Desharnais is another right-handed shot and a strong penalty killer. He’s also a pending UFA and movable, but he’s currently week-to-week with an upper-body injury.
You can’t trade a guy who can’t pass a physical.
Then there is Timothy Liljegren — right-handed, pending UFA. He seems like a viable option to jettison for a mid-round pick, but again, does the asset return outweigh the sacrifice of depth during a grueling stretch run?
And we haven’t even touched the emotional third rail: Mario Ferraro. It would feel wrong to trade Ferraro now. He survived the lean years. He bled for this team when they were losing 10-1.
But his name is constantly bandied about in trade chatter, and the Sharks need to make a call on him before he hits unrestricted free agency this summer.
Up front, the math is just as calculus-heavy.
Every contender in hockey wants center depth. They will all want Alex Wennberg. He’s a pending UFA, responsible, and steady. But if you move Wennberg, who takes the minutes? Do the Sharks really want to play rookie Michael Misa 15-plus minutes a night, down the middle, in the thick of a playoff hunt? That’s how you break a prospect, not build one.
Jeff Skinner? He was ostensibly acquired to be flipped, but he hasn’t played enough or well enough to elicit a serious market.
And Grier has to weigh the human element here, too. Don’t forget that last season, with the Sharks nowhere near a playoff spot, Grier traded Mikael Granlund and Fabian Zetterlund at the deadline. On paper, those were clear wins: Asset management 101.
The room didn’t love it, though. There was some dragging of feet after both moves, even though the Sharks eventually played better hockey down the stretch without them.
That kind of vibe should probably be avoided this season, especially when the games actually matter.
The young Sharks — led by Celebrini and Will Smith — have forced their front office to make a call: Now or later? Good luck trying to thread that needle.
Do you reward the boys for their overachievement by keeping the group together, or do you stick to the long-term plan and sell expiring contracts to bankroll the future, morale be damned?
There might not be a clear answer at the moment — both arguments carry serious merit. But make no mistake, we’ll know by the end of the season if the Sharks made the right one.