Cavaliers owner Dan Gilbert reportedly very unhappy with Cleveland's struggles

It’s certainly fair to say that changes could be on the horizon for the Cleveland Cavaliers.

After losing two games in the same week to the lowly Chicago Bulls, the Cavs can only use their injury excuse for so much longer.

While they are currently without Evan Mobley, Sam Merrill and Max Strus, it feels like sweeping changes could be on the way for the NBA’s only second apron team.

According to Cleveland.com’s Chris Fedor on his “The Wine and Gold Talk Podcast,” Cavs owner Dan Gilbert is frustrated with the team’s 15-14 start.

“Two sources with knowledge very close knowledge to the situation say that Dan Gilbert is very unhappy with what is going on,” Fedor said.

The Cavaliers have been booed on their court four times in their last five home games. The Cavs have lost embarrassing games to bad teams including the Bulls, Golden State Warriors without Stephen Curry, Charlotte Hornets and Portland Trail Blazers within the month.

Certainly the team is frustrated. Head coach Kenny Atkinson sounds exasperated in his postgame press conferences. And the frustration has officially boiled all the way to the top of the organization.

“He’s paying a huge luxury tax bill, it’s the highest payroll in the NBA, it’s the only team in the second apron,” Fedor said. “And he’s willing to do that when he thinks the team has a chance to win the championship. But it’s not that early anymore.”

Sources tell @ChrisFedor it’s not just frustration in the #Cavs’ locker room — it’s reached the top.

Dan Gilbert is reportedly unhappy with what he’s seeing and starting to get more involved. For anyone who knows how he operates, that’s a wildcard the team can’t ignore. pic.twitter.com/ULEGw4zcGM
— The Wine and Gold Talk Podcast (@WineGoldTalkPod) December 20, 2025

It’s true. The Cavs have the most expensive roster in the history of basketball. The core four of Donovan Mitchell, Mobley, Darius Garland and Jarrett Allen are all paid very handsome salaries. Through the first 29 games of the season, Mitchell is the only one who has lived up to expectations.

Apparently, the owner might not believe that this group can win a title as currently constructed.

This was supposed to be a make or break season for the Cavaliers. In Mitchell’s first year with the Cavs, the team flamed out in the first round against the New York Knicks. Following that, back-to-back second-round exits put pressure on President of Basketball Operations Koby Altman.

But Altman stuck to his core. He decided to follow the championship blueprint of building around the young nucleus and improving on the margins, adding Lonzo Ball, Larry Nance Jr. and Thomas Bryant this offseason.

So far, none of that looks to be the right move. The Cavs have played more than a quarter of their regular season and currently would be slotted to have a NBA Play-In Tournament game. Obviously, ownership believes that’s unacceptable for how expensive this roster is.

The Cavaliers have back-to-back tune up games on Monday and Tuesday against the Hornets and New Orleans Pelicans. Then, they travel to Madison Square Garden for a Christmas Day matchup with the Knicks on Thursday.

Many people around the basketball world anticipated a Cavs vs. Knicks Eastern Conference Finals. If the Cavs are embarrassed on Christmas Day, Gilbert might not have any choice but to shake things up in a major way.