Looking Back at the Cleveland Cavaliers’ Last Two Offseasons

The 2026-27 season is approaching, and the Cleveland Cavaliers are shooting for a championship. Their playoff run came to an end after a disappointing series against the New York Knicks, and now, they want to recover from that loss and become champions in the process. However, they will have some competition.

This offseason started off strong, as numerous stars found new homes. For example, two-time MVP Giannis Antetokounmpo will suit up for the Miami Heat. The Heat sent Tyler Herro, Jaime Jaquez Jr. and others to the Milwaukee Bucks in exchange for Antetokounmpo and Bobby Portis. Then, another Eastern Conference team made moves, as the Philadelphia 76ers acquired Jaylen Brown in a trade, and they signed LeBron James later on.

As far as Cleveland goes, this started off as one of the quieter offseasons. However, they have their wing, as they acquired Peyton Watson in a recent trade. So, that makes a difference, and the Cavs have completed a deal they have been waiting on.

When it comes to the Cavs' other moves, they retained some of their players. They exercised their team option on Craig Porter Jr., and they re-signed Thomas Bryant a bit later. Then, star guard Donovan Mitchell signed a four-year extension, and the Cavs spent time trying to finalize a deal with his backcourt running mate.

James Harden opted out of his deal, and after the Watson trade, he signed a three-year, $97 million contract. Now, Cleveland's backcourt will get ready for its first full season.

Cleveland added some new faces, and one of them was a draft pick. The Cavs drafted Meleek Thomas in the second round, and he turned heads with his Summer League performance. On top of Thomas, the Cavaliers found another young talent, as they signed Ernest Udeh Jr. to a two-way contract. Udeh went undrafted, but he showcased his rim-protecting abilities in Las Vegas.

Cavs Bring In Former Lottery Pick

The Cavaliers also brought in a former lottery pick, as they signed Mario Hezonja. Hezonja established himself overseas, and now he is getting another shot at the NBA. He was drafted by the Orlando Magic, and after three seasons with them, he played for the New York Knicks and the Portland Trail Blazers.

Cleveland was involved in a recent move as backup point guard Dennis Schröder will be joining the Charlotte Hornets. The Cavs are getting Tre Mann in return, and he will be on the move due to the Watson deal.

Until now, this offseason had very few moves. But in 2025, the Cavaliers added a few players. They retained Sam Merrill, as he signed a four-year, $38 million deal. Luke Travers returned after signing a two-way deal, and later in the season, he was waived. Cleveland signed two bigs during that offseason, as Bryant and Larry Nance Jr agreed to deals. The Cavaliers also drafted Tyrese Proctor, and he averaged 5.4 points in 50 games.

On top of their signings, the Cavs made a trade. They sent Isaac Okoro to the Chicago Bulls in exchange for Lonzo Ball. Later on, Cleveland traded Ball to the Utah Jazz, and he was waived.

The Cavaliers' recent offseasons have been about filling voids, and some moves worked out better than others. Bryant gave them a backup big, Ball gave them a backup point guard in his stint, and now, they have help in another area.

Cleveland's offseason has dragged up to this point, but with the addition of Watson, things are looking up.

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