Cavaliers Should Make This Key Player a Priority for a Contract Extension

The good news in Cleveland is that, unlike with most teams, the entire starting five is locked up. No, really. For at least the next three years, all five players are secured with deals and paydays.

Might this be an issue down the line? That’s for another day, because on paper, coming into 2026-27, that’s a fantastic thing to have. Not having to worry about paying the big bucks to any of your core players is significant. But there is one who is not locked up long-term heading into year three.

If you haven’t guessed it yet, we’re getting there.

Pay Jaylon Tyson!

James Harden got his long-term deal. Donovan Mitchell signed a max four-year extension. Peyton Watson is also now good for four years. Evan Mobley has four more seasons, while Jarrett Allen has three. Plus, Sam Merrill is solid through 2028-29.

The top six guys here are all locked in, and that leaves one more guy deserving of a big pay check. The Cavs have team options on Jaylon Tyson for the next two seasons at just over $5 million. After being a mid-first-round pick, that’s about what the figures would be. And it’s definitely time to make sure they can keep him around.

Expansion drafts will be happening in the next offseason or two to fill the roster of the new Las Vegas and Seattle teams in the NBA. Only eight players can be protected. It would be fantastic for Cleveland if they gave the long-term deal and production to their talented wing so he can stick around.

The incredible year one to year two improvement for the wing was easy to see for everyone. He nearly tripled his scoring output. Tyson hit 45% of his shots from beyond the arc. He even had a 39-point night against the Sixers in a Nationally televised game on ESPN.

He brings a lot of 3 and D, along with hustle, energy, and leadership, and needs to get his money.

Payment Timeline?

Ideally, things go well this year so that Jaylon Tyson can be paid by team option next year at $5 million again. Once this season is finished and that’s done, they can find a common ground on a rookie extension. There is a near-zero chance he gets a max deal. But he should be getting paid at minimum, double or triple what he’s getting right now.

Going into 2028-29, the hope will be to see Tyson with his new deal. He and Merrill are going to be the core reserves on this year’s squad, and their play is very significant in seeing where this squad can actually go.

So look for a hopeful late-summer timeline for Tyson, pending that the team (more than likely) pays via team option, and then switches for the long-term moola.

Being the invaluable player he is, it will be great to see that day come for JT.

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