How teams and star players would benefit from shorter-term contracts

By now, the stories have been well-told.

Dylan Larkin asked for a trade in year four of an eight-year deal. Connor Hellebuyck asked for a trade in year three of a seven-year deal. Brady Tkachuk made it to year six of his before he wanted out, which was granted before year seven began. All of these players wielded no-trade clauses that hampered any potential return their teams could get, which was a bad deal for the fans twice — they lost a star, and recouped little for him. 

For these and other elite NHLers, I understand the desire to sign for eight years the second you have a team willing to give it to you. But when it came to these truly top-end guys, the “give me the max dollars and length” always felt like contracts written with crayons rather than calligraphy. 

Sure you're able to get a big long-term deal, but if you're a proven top-end player in the NHL, wouldn't you want to maintain some flexibility on where you play?

The way Auston Matthews has done his contracts has always made sense to me. He's signed five- and four-year contracts after his entry-level deal with the Leafs and has made good money, but never sought out maximum length. Five years is a big commitment to a city, isn’t it? And really, who among us knows what our priorities will be in five years? “I’m happy to re-up when we get there, let’s just re-assess if everyone’s happy” is a thought process I’ve never wavered in defending.

If you have priorities beyond money (as most of us do), it might be wise to build those concerns into your contract. Now the likes of Larkin, Hellebuyck and Tkachuk have paid the price with the tattered legacies they leave behind on teams they gave so much time to. 

But it's hard to fault them. The threat of catastrophic injury is real. Everyone around them is surely advising to take the guaranteed money, who knows what can happen in the future, so lock yourself in.

However, I’d argue in favour of more deals like Matthews'. It's a strategy that still gets you paid, and I'd also point out that signing for maximum term ignores the risk of missing out on other things, like signing another deal in a rising cap world, or the possibility the organization changes in a way you don't support.

Now more than ever, a skyrocketing salary cap means things around the NHL are going to be very different, and how teams and players consider term should become their new focal point. 

Look, it’s bad for everyone when a player signs for a long term and then asks out. But it’s also not great when players hold teams over a barrel and ask for term when they’re older, as we’re seeing happen with Nikita Kucherov.

Eating a huge percentage of a team's cap as your game erodes away late into your 30s and early-40s hurts your team, makes for tense relationships, and opens the door to tarnishing your legacy in a different way. 

Yes, Kucherov is 33 and at the point in his career when guys are looking for maximum dollars to get their biggest, last payday, so his scenario is a little different than most.

In Kucherov's case, and those like him, it’s on the team. You don’t want to come off like Julien BriseBois and the Lightning where you look like you're being insensitive to a franchise icon, but you do have to protect yourself.

In the case of guys like Tkachuk, Larkin or Hellebuyck, players shouldn't always go long-term when the cap is rising, and the league is changing so much because you may not really know where you want to be in time. And you'd likely make more money by not signing for so long, then being able to sign another big contract.

In both cases, the answer is to overpay players to get them to agree to a shorter term. That’s all this whole article is about. Pay the costs up front.

For players, there is a lot of value in getting big dollars up front as you can put the money in places where it goes to work for you sooner. If things go well, another big contract will come down the road. If things don't go well, an extension may be for less money but, you've been able to bank excess money up front. And even with that trade-off, you still might make the same amount over two contracts as you would have with one, but you've maintained some personal flexibility.

The idea of overpaying someone up front to get them signed for less term may sound unusual, but that's only because this route simply hasn't been an option over the past decade.

A few years ago, 90 per cent of the league was spending within a couple million dollars of the cap. Nobody had any room or flexibility, so to bring down AAVs, GMs gave term and no-move clauses. Those two things in concert make for the ugliness we’re seeing today, but these teams had to do anything they could to avoid high AAVs.

With the salary cap launching upwards, the calculus has changed. Earlier last week, we saw some articles about how in three years the cap could be at a whopping $150 million. 

For context, from 2018-19 to 2024-25 the cap sat between $79.5 million and $83.5 million. It’s $104 million today, going to over $113 million next year, and will threaten $130 million the year after that, once the post-Covid correction sets in (the cap had been artificially deflated for a few years for reasons we don’t need to bother with today).

So, on the way to $150 million, suddenly some players can make the maximum 20 per cent of the cap and a team can still have room to fill out the rest of the roster. We’re all going to switch away from this type of un-fun fan-mode we’ve had to learn where we judged players so stringently against their cap hit, because salary cap efficiency was as relevant as who had the best players. Inefficient contracts killed your chance to build a team (a pain fans of the Maple Leafs felt all too strongly for a while).

But as you look at the direction things are going now, something else should stand out: there are 32 teams in the league and more could be added. There’s not enough elite talent to go around. Getting and keeping the best players is a number one priority, because they’re tough to land in the first place.

So with a guy like Kucherov, you can’t get caught up worrying about an efficient deal. Instead should just make sure you A) keep him and B) don’t give him those fifth and sixth years where you worry he’ll become something closer to this year’s Alex Ovechkin, an elite star who’s just gotten to the end of the line. The offer can’t be for $13 or even $15 million. You have to push your chips in hard and go in on a shorter-term deal. That first offer should’ve been closer to 4x20.

If he walks in that scenario, at least you’ve got the PR advantage by being able to tell your fans that you tried to make him the highest-paid forward in the league for the next three seasons.

These types of deals can even extend to UFAs that intrigue a team. Big dollars for short term allows you to get the talent you want without messing up the future if the fit isn’t right, or if their play declines. Paying real dollars rather than trying to add value with no-move clauses helps a team maintain flexibility, too.

For the next wave of superstar contracts -- particularly to older players -- teams shouldn't just lay down maximum term deals because “that’s what the good players get.” Players who’ve earned a lot and proven themselves in the league should recognize the value of future flexibility and money in their bank accounts today. And teams should recognize that paying more up front allows them to maintain their own flexibility, rather than getting trapped with a non-Cup level team that’s locked in for most of a decade because they chased "contract efficiency" a little too hard. 

Pay the stars, and pay them well, but don’t go long on term. If this is what the “player empowerment era” is going to look like both sides are going to want flexibility, and that’s something worth paying for up front.