Owner Dan Gilbert has been “very unhappy” with the Cavaliers‘ performance this season, particularly over the past few weeks as the team has dropped eight of its last 11 games, Chris Fedor of Cleveland.com reported on the Wine and Gold Talk podcast (YouTube link).
The Cavaliers have lost three straight games, starting with Charlotte last Sunday. The past two losses have come at the hands of Bulls, another team that had been struggling. Going back a bit further, the Cavaliers barely beat the lowly Wizards last week and lost at home on Dec. 6 to a Golden State team that was missing all of its top players.
“Two sources with knowledge of the situation, very close to the situation, say that Dan Gilbert is very unhappy about what is going on,” Fedor said. “He turns on the games and he hears boos? Four times in the last five home games? Turns on games and sees the Cavs trailing by double digits again. Sees the Cavs leading by one minute in the second half of these games.
“And he’s paying a huge a luxury tax bill,” Fedor continued. “It’s the highest payroll in the NBA. It’s the only team in the second apron. He’s willing to do that when he thinks the team has a chance to win the championship. When he believes in the group that he has. But it’s not that early anymore. … When you see this 29 games in, you start asking questions if you’re the guy in charge with everything in this organization.”
As Fedor mentioned, the Cavaliers are operating over the second tax apron, which will limit their roster flexibility in the coming weeks. The team’s luxury tax bill is currently projected to be nearly $164MM, per Spotrac.
The Cavs held the best record in the Eastern Conference — and second-best overall — in 2024/25 when they finished 64-18. They lost to Indiana in the second round of the playoffs but largely ran back the same roster in the hope of making a deeper playoff run.
However, things haven’t gone as planned through about 35% of the season. The Cavs have dealt with several injuries to key players and haven’t looked anything close to last year. They’re currently 15-14, the No. 8 seed in the East.
Fedor said members of Cleveland’s front office have been trying to allay Gilbert’s concerns by stating that Max Strus, Sam Merrill and Evan Mobley will eventually return from their respective injuries. Still, Fedor suggested that Gilbert has become more involved in the basketball operations department of late and that could factor into the team’s moves ahead of the trade deadline.