Since 2016, Doug Wilson Has Been Handing Out Longer Contracts to Older Players

How did the San Jose Sharks get stuck in purgatory?

By purgatory, I mean the Sharks currently occupy a place between a true Stanley Cup contender and a likely cellar-dweller.

I broached the topic with Dimitri Filipovic on PDOcast yesterday:

New PDOcast with @Sheng_Peng🎙:

•Rebuilding the Sharks
•How they got to this point
•Paying the price for being good
•How they can bounce back
•Separating goaltending from defense
•Running offense through defensemen
•The plan moving forwardhttps://t.co/oD9UzsDQTY

— Dimitri Filipovic (@DimFilipovic) December 4, 2020

But let’s dive deeper.

A pair of entwined paths have led the Doug Wilson-run organization down this road: Failure at the draft table and long-term contracts to older stars that backfired last year.

We’re going to focus more on the contracts here, but to underscore the point about San Jose’s drafting woes, from 2013-20 — and allowing, obviously, that the more recent picks can’t be judged yet — the Sharks have only produced two or three sure-fire NHL regulars, Timo Meier, Kevin Labanc, and possibly Mario Ferraro. Essentially, as San Jose was getting older up top, the team wasn’t replenishing itself from the bottom with enough young talent.

Let’s put it another way — let’s divide San Jose Sharks’ drafting eras by three and count the NHL regulars.

• 2013-17: (Timo Meier, Kevin Labanc, Mario Ferraro — we’ll see if Josh Norris, Joachim Blichfeld, Noah Gregor, or Sasha Chmelevski become NHL regulars — I doubt that they all will)
• 2008-12: (Tommy Wingels, Jason Demers, Charlie Coyle, Matt Nieto, Dylan DeMelo, Sean Kuraly, Tomas Hertl, Chris Tierney)
• 2003-07: (Milan Michalek, Steve Bernier, Matt Carle, Joe Pavelski, Thomas Greiss, Torrey Mitchell, Devin Setoguchi, Marc-Edouard Vlasic, Jamie McGinn, Logan Couture, Nick Bonino, Justin Braun)

Beginning with Wilson’s first draft as GM in 2003, we can observe diminishing draft returns every half-decade, culminating in a potentially dry 2013-17 that’s leaving the Sharks parched right now.

Let’s talk contracts next.

For the first 13 years of his tenure, Wilson appeared steadfast in his resolve to not hand out long-term contracts, especially to veterans. Such agreements clearly have a way of crippling franchises in the salary cap era.

From 2003-16, the longest contract that Wilson handed out was six years for $26 million to Milan Michalek — a 22-year-old coming off a 26-goal sophomore campaign. It’s worth noting that every NHL franchise except for the Arizona Coyotes had at least one seven-year or longer agreement signed in this stretch of time.

Seven San Jose players were given five-year pacts — Jonathan Cheechoo, Brent Burns, Marc-Edouard Vlasic, Logan Couture, Joe Pavelski, Justin Braun, and Brenden Dillon — the oldest of this group was Pavelski, 29, in July 2013, and average age, including Michalek, was 25.

Everything changed in November 2016, when Wilson inked a 31-year-old Burns to an eight-year, $64 million dollar agreement.

“I think he’s just coming into his prime,” Wilson told the Mercury News, “and he’s only going to get better.”

In fairness to Wilson and Burns, this was more-than-appropriate value at the time — this made the impending UFA the second highest-paid defenseman in the league after P.K. Subban at $9 million per. The Norris Trophy finalist certainly would’ve commanded more on the open market.

And as wild as it appears for Wilson to claim a 31-year-old was “coming into his prime” and “only going to get better,” the hulking blueliner promptly took home the 2017 Norris, finished eighth in 2018, and was 2019 runner-up.

This signaled an apparent sea change in San Jose Sharks philosophy.

Since Burns, Wilson went on a spending spree, tossing out five more six-year plus contracts — six years and $34.5 million to Martin Jones and eight years and $56 million to Marc-Edouard Vlasic in July 2017, seven years and $49 million to Evander Kane in May 2018, eight years and $64 million to Couture in July 2018, and eight years and $92 million to Erik Karlsson in June 2019 — average age, including Burns, 29.

Comparing 2003-16 to 2016-20, that’s more term for players that are, on average, four years older. In fairness to Wilson, all these agreements, except perhaps Jones’s were equal or less than probable market value at the time. Regardless, only the Nashville Predators, and remarkably, the Vegas Golden Knights, both tied at seven, have doled out more six-year plus contracts since November 2016.

This brings us to this off-season, reeling from a 2019-20 where every one of these expensive stars, save Kane, underperformed relative to their contracts.

Of course, that’s not news to anybody — the larger question is, what brought about this organizational shift?

• Was this simply the price of business to keep your stars in the modern era?
• Was it some belief that today’s training methods — evidenced by franchise linchpins like Joe Thornton and Patrick Marleau and Pavelski and Burns aging gracefully in their early 30s — would hold true with the other players?
• Was it simply easier to commit less when stars like Thornton and Marleau, in their primes, were willing to accept three or four-year offers: Did Burns’s landmark agreement inadvertently open the floodgates?
• Was it the success of the 2016 Sharks, two wins away from the Cup — and even the 2019 group, two victories away from the Final — that pushed Wilson to make increasingly dangerous bets? To win one for Jumbo or Patty or Pavs?
• Was it just bad luck: Could Wilson have foreseen such dramatic drop-offs from Jones, Vlasic, and Karlsson? Also, as a reader mentioned in the comments below, Wilson probably counted on the salary cap rising, which would’ve made any bad contract a little less onerous.

As I’ve said before, the idea with these lengthy contracts for veteran stars is you pay for the first four years, you pray for the last four.

But in the case of Karlsson, for example, you’re praying for the next seven.

Anyway, there’s hockey heaven and the Stanley Cup, there’s the hell that through high draft picks helps you get to heaven — and then, there’s purgatory.

It’s a place with stars — but with long contracts that you can’t shed to re-allocate cap space. It’s a place with prospects — but who don’t look likely to enter their primes when your stars are your stars.

Of course, that’s one definition of purgatory, a situation neither good nor bad — but there’s also the more classic definition, where souls can make up for past sins and get their way to heaven.

In 2014-15, the San Jose Sharks missed the playoffs for the first time under Wilson. There were similar whispers about that aging group. And we know how that story ended.

But I don’t know. In this case, it’s hard to see where these Sharks can get to heaven before they close the door.

Special thanks to the Locked On Sharks guys — Kyle, Erik, and JD –for being a sounding board for this article.