David Richard-USA TODAY Sports

Confidence is key and Cleveland Cavaliers owner Dan Gilbert knows that as well as anyone. But when it comes to five-time All-Star, Donovan Mitchell, the 62-year-old isn’t blowing hot air. He genuinely believes Mitchell will sign a contract extension to remain with the Cavs after they traded for him in 2022.

“We’ve been talking to him, sure, for the last couple of years about extending this contract,” Gilbert tells Larry Lage of The Associated Press. “We think he will extend. I think if you listen to him talk, he loves the city.”

As for why Mitchell will want to stay?

“He loves the situation in Cleveland,” Gilbert claims, “because our players are very young and we’re just kind of putting the core together that he’s clearly the biggest part of.”

Mitchell, who signed a five-year contract with the Utah Jazz in 2020, is signed through the 2025-26 season. However, Mitchell can decline the player option on the final season of his contract and become a free agent next summer. He’s eligible to sign a four-year, $200.4 million contract extension with the Cavs.

Among the teams with marquee players who could become free agents by 2025, the Cavs may have the most difficult challenge ahead of them.

The New York Knicks’ Case

After two seasons with the Cavs, Mitchell will finally have the opportunity to play for a team in New York. For years, that organization has been thought to be the Knicks because of Mitchell’s northeastern roots. Born in New York and raised in New Hampshire, Mitchell’s father is a New York Mets executive.

Looking at the Knicks’ current roster construction, he’d easily step into Donte DiVicenzo’s shoes. It would require the Knicks to rely less on breakout star Jalen Brunson. For his part, Brunson has to be more willing to share the load. However, with Brunson’s injury history, he and New York could see the benefit.

Armed with four first-round picks in the 2024 NBA Draft, it wouldn’t be surprising if they made a run at Mitchell this offseason. With those picks and a player such as OG Anunoby as the headliner, the Cavs may bite on the deal. Especially if they feel that’s where Mitchell prefers to be.

The Brooklyn Nets’ Case

The Brooklyn Nets could also find themselves on Mitchell’s shortlist. Despite their ‘little brother’ status in New York, the Nets have three star-caliber players on their roster. Major front office and coaching staff roles need to be filled. Subsequently, the Nets can bring in an assistant general manager and head coach with a plan for constructing a team around Mitchell.

Should they retain Cam Thomas and Nic Claxton this offseason, their next course of action could be to pry Mitchell away from the Cavs. In this scenario, Mikal Bridges has as much of a chance to be a foundational piece for the Nets as trade bait. With three first-round picks in the 2027 NBA Draft, they could further entice Cleveland. However, they appear to be a bigger threat to acquire Mitchell next offseason than this summer.

The Cleveland Cavaliers’ Case

Of course, Mitchell truly could remain in Cleveland. He’s grown fond of his teammates, the franchise, and the city. The Cavs have also won plenty of games, going 77-40 with Mitchell in the lineup. Their .658 win percentage with Mitchell would make them a 54-win team in a regular season.

That being said, money and wins talk the loudest in contract negotiations. To that point, the Cavs can pay Mitchell more than any other team. They can also offer as much chance to win as any of the teams linked to him.

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