Cleveland has a rare kind of roster comfort right now: the starting five is already accounted for, and not just for next season. In fact, all five starters are under contract and paid through at least the next three years, which gives the Cavs a level of stability most teams would love to have heading into 2026-27.
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.
Sam Merrill is also locked in through 2028-29.
That leaves one name standing out as the guy who should be next in line for a real payday: Jaylon Tyson.
Right now, Cleveland holds team options on Tyson for the next two seasons at just over $5 million, which is about what you’d expect for a mid-first-round pick. But after what he showed in his second year, the time to start planning for the bigger deal is now.
The wing’s jump from year one to year two was obvious. He nearly tripled his scoring output, shot 45% from three-point range, and even put up a 39-point night against the Sixers in a nationally televised game on ESPN.
Tyson fits the mold of the modern role wing: 3-and-D ability, hustle, energy, and leadership. That kind of player matters, and Cleveland knows it.
There’s also a bigger roster wrinkle coming soon. Expansion drafts are expected in the next offseason or two to help stock the new Las Vegas and Seattle teams, and only eight players can be protected. That makes locking in the right pieces even more important, especially for a young wing with real value.
The ideal path is pretty clear. Let this season play out, pick up the team option next year at $5 million again, and then work toward a rookie extension after that. Tyson is not headed for a max deal, but he should be making at least double or triple what he’s on now.
By 2028-29, the hope is that Tyson is already operating on his new contract and serving as one of the core reserves alongside Merrill. Their impact will matter a lot in determining how far this Cavs group can go.
For Cleveland, the next step with Tyson should be straightforward: keep him, pay him, and make sure a player this useful doesn’t get away.
In Other News...
Former Cavs Are Headed Back To Cleveland With Plenty At Stake
The Cavaliers are about to see a familiar wave of faces come back through town, and this time the stakes feel bigger than a routine reunion. LeBron James has landed with the Philadelphia 76ers, forming a loaded group with Joel Embiid, Tyrese Maxey and Jaylen Brown, while Dean Wade is also back in the same mix after seven seasons in Cleveland.
Cleveland will also get visits from Darius Garland and Max Strus, now with the Houston Rockets and Los Angeles Lakers, and both arrive with their own uncertainty hanging over the season. Kyrie Irving, meanwhile, remains a possible trade candidate and is slated to be in Cleveland in mid-November, giving the Cavs another reminder of how much the franchise's recent past could still shape what comes next. [Read more 🡒]
Jarrett Allen's Cavaliers Role Suddenly Feels Far Less Secure
The Cavaliers spent the offseason looking for ways to add more size and flexibility on the wing, and Peyton Watsons breakout 2025-26 season gave them a clear reason to keep exploring that direction. But any move that tilts the roster farther toward perimeter depth also raises an old question in Cleveland: how much room is there, really, for Jarrett Allen to stay fully involved in the offense when the lineup keeps evolving around him?
Allen has long been most effective when he is more than just a rim-running presence, and last season offered another reminder of how valuable he can be when the ball finds him in better spots. The challenge now is making sure the Cavaliers do not crowd him out as they chase more versatility elsewhere, which leaves plenty of room for lineup tinkering and a few decisions that could shape how secure his role feels once the real games start. [Read more 🡒]
Jarrett Allen Looms Over Cavs' Long-Term Title Push
The Cavaliers have already made their intentions clear by leaning into a core built around Evan Mobley, while adding Peyton Watson and extending James Harden to keep the title pursuit on track. Even with that direction set, Clevelands roster still carries the kind of moving parts that can shape what comes next, especially in a front office led by Koby Altman, who has shown a willingness to make midseason changes when the need arises.
Jarrett Allen sits at the center of that conversation because of what he means to the current lineup and what his future might look like if the season does not match the teams expectations. Some around the league believe Allen could emerge as a trade candidate, though any move of that sort would also push Mobley into more time at center, a shift that would change both the rotation and the way the Cavaliers imagine their long-term title push. [Read more 🡒]