Top 3 Priorities for Cleveland Cavaliers During 2026 NBA Offseason

Often outworked and sometimes unable to match the Toronto Raptors' defensive intensity during a seven-game first-round escape, the Cleveland Cavaliers went the distance for a second straight series against the top-seeded Detroit Pistons.

After surviving that matchup by the narrowest of margins, the Cavs finally ran up against an opponent too good to sneak past. The New York Knicks hammered Cleveland in a four-game sweep that highlighted the chasm separating separating it from the true title-threat class.

Now, after a bumpy regular season that gave way to glimpses of fringe-contender quality in the playoffs, the Cavs face an offseason full of uncertainty.

Donovan Mitchell and James Harden are integral pieces to the team's core, though both guards had deeply disappointing playoff stretches. Will the Cavs continue to build around their current stars, both of whom are extension eligible? Or will they be forced to consider alternatives after yet another underwhelming postseason appearance?

Hard choices loom, and an extremely costly Cavaliers roster could undergo serious changes this summer. Let's see what Cleveland will focus on first as it tries to regroup.

1. Donovan Mitchell's Extension

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Donovan Mitchell is eligible to sign a four-year, $277 million extension this summer, and the Cavs can't move on to any other offseason business until their best player's future is settled.

Months ago, ESPN's Tim Bontemps speculated that Mitchell would be unlikely to extend if Cleveland failed to advance past the first or second round of the playoffs.

In the time since the trade, Mitchell has reaffirmed his commitment to the team and happiness in Cleveland whenever asked. He's compensated fairly, the organization is trying to win and there's even some upside if Evan Mobley takes another step forward. Mitchell's stated satisfaction might be real. Or it might not.

We won't have to guess at his true state of mind once the Cavaliers push that extension offer across the table. His decision on whether or not to sign it will be the ultimate tell.

If Mitchell opts to play out the last guaranteed year of his deal next season, he can decline his 2027-28 player option to enter unrestricted free agency. That's an outcome the Cavs must avoid, which means trade talks and a potential franchise reset could follow Mitchell's refusal to sign.

If he re-ups, Cleveland's attention will shift to keeping a contending roster around its cornerstone.

2. James Harden's Next Deal

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James Harden has a $42.3 million player option for next season that he is expected to decline, per Fred Katz of The Athletic.

Unrestricted free agency won't present many appealing options for the veteran guard, as most cap-space teams—such as the Brooklyn Nets, Chicago Bulls and Los Angeles Lakers—are unlikely to prioritize him given their current timelines and roster needs.

A lack of landing spots won't allow the Cavs to play true hardball, as retaining Harden will be important to keeping Mitchell happy and the team in the fringe-contender class. Plus, it's tough to imagine the Cavaliers would have onboarded the former MVP at the deadline without discussing future salary parameters.

It's similarly unlikely Harden would have steered himself to Cleveland without knowing a new deal was coming this summer.

The Cavs should be able to retain Harden on a two-year deal with a player option on the second season. That would be in keeping with the trend of the last several years, during which Harden has signed two-year contracts with the Philadelphia 76ers and LA Clippers worth $68.6 million, $70 million and $81.5 million, respectively. If Cleveland can get something done for around $80 million in total, everyone should be satisfied.*

*Until Harden becomes unsatisfied, which tends to happen every year or so.

3. Find a Fifth Starter

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If we assume Mitchell, Harden, Mobley and Jarrett Allen are all back, the Cavs will then move on to solidifying their fifth and final starting spot.

Some will argue Jaylon Tyson did enough during his second season to deserve the position. Others will point out that Max Strus, when healthy, is a good enough option. Free agent Dean Wade has his supporters, not to mention years of flattering on/off splits. Sam Merrill, free agent Keon Ellis...the list goes on.

Consensus has been hard to come by for years, and that's the point.

If it seems like the Cavs have several good answers at small forward, it actually means they don't have a great one.

As a likely second-apron team, it won't be easy to secure the kind of wing Cleveland needs. It's not as if 6'8" defenders who can hit threes at a high clip come cheaply.

Trading Allen would be one option, but it's difficult to imagine many teams will be eager to take him on just as his three-year, $90 million extension kicks in.

The hole at the 3 has been a known issue in Cleveland since the current core came together. While securing Mitchell and Harden remain the team's top two priorities, it's worth pointing out that poor production between the Cavs' favored "two bigs and two smalls" setup has consistently cost them.

Stats courtesy of NBA.com, Basketball Reference and Cleaning the Glass. Salary info via Spotrac.

Grant Hughes covers the NBA for Bleacher Report. Follow him on Bluesky and subscribe to the Hardwood Knocks podcast, where he appears with Bleacher Report's Dan Favale.