3 Biggest Questions Around Cavaliers Entering 2026-27 NBA Season

The 2026-27 NBA season has a championship-or-bust mentality for the Cleveland Cavaliers following another deep playoff run.

Cleveland reached the Eastern Conference Finals last year, but the team was swept out of the round. Now, the Cavaliers believe that they have a stronger roster that is more equipped to handle the pressure of the playoffs.

But the Cavaliers are going to have to earn their keep in the Eastern Conference this season, and teams all over have gotten better too. Cleveland's core group gives them a fighting chance every time on the floor, which not every team can say.

So, entering the year, the pressure is on the Cavaliers to deliver this year. Here are three of the biggest questions surrounding Cleveland entering the new season:

1. Can Peyton Watson Live Up to His Massive Contract?

Watson signed a huge four-year $88 million deal with Cleveland over the offseason, and with this comes more expectations. The Cavaliers believe that Watson can be the missing piece for the team, but he will have to prove himself throughout the year.

The defensive forward will be tasked with taking on the toughest assignments against opposing teams, while also knocking down three-point shots consistently. Watson is the classic three-and-D wing that every team in the league wants to have, and the Cavaliers have one of the best in the business now.

2. Can James Harden Perform in the Playoffs?

This question has become a running joke in some ways throughout Harden's career. But in all reality, it's a fair one since his career numbers drop when the lights are brightest.

Since Cleveland has Donovan Mitchell as the main star, all the pressure isn't on Harden to deliver, but he does need to do his part. And if Harden can finally break through the narratives around him, the Cavaliers could seriously be a major threat to win it all this season.

3. Can Evan Mobley Become Better Offensively?

Mobley has been great since the Cavaliers drafted him years ago, but the team still needs him to be a little more consistent offensively. The big man has been excellent on defense, but if he can develop more of an offensive game, Cleveland could fully take off.

Last season for the Cavaliers, Mobley averaged 18.2 points, 9.0 rebounds, 3.6 assists, 0.7 steals, and 1.7 blocks per game. But his three-point shot percentage dropped to 29.7, which he is going to have to increase this season, and by doing so, will help the offense flow much smoother.