CLEVELAND, Ohio — Donovan Mitchell and the Cavs are barreling toward what could be the most consequential contract negotiation in franchise history.
The numbers are staggering: a potential five-year, $380 million extension when Mitchell becomes eligible in 2027 after completing his 10th NBA season.
But as the latest Wine and Gold Talk podcast reveals, what initially appears to be a player-controlled situation might actually present a profound dilemma for both sides.
“The power of this situation is solely in the hands of Donovan Mitchell,” says podcast host Ethan Sands. “Don’t want to sign an extension? Cool. That’s up to you. Don’t want to sign the player option? Cool. Want to sign the biggest contract that you’ve ever had? Makes sense. But is that indicative of what you believe as a player is going to help you have the most success?”
That’s where cleveland.com columnist Jimmy Watkins pushes back with a perspective that flips the conventional wisdom: the Cavaliers might actually be the ones with leverage — and with an excruciating decision to make.
“Do the Cavs want to give him all that money at that point? If he’s going to be 31 by then ... That’s almost 80 million a year,” Watkins argues. “If you miss on a contract like that, that window, early to mid-30s is when the drop off usually comes. If you miss on that, you’re screwed.”
The stakes couldn’t be higher.
By the time Mitchell is eligible for this mammoth extension, Evan Mobley will be entering his prime years. The financial commitment to Mitchell would effectively define the Cavaliers’ championship window and team-building strategy for the next half-decade.
“I love Donovan, and I think he takes great care of his body and he’s all about all of the right things,” Watkins points out. “[But] Father time is undefeated. This is going to be a very tricky negotiation for the Cavs.”
The contrast with the Cavaliers’ initial acquisition of Mitchell is striking.
When Cleveland traded for Mitchell, the team was desperate to secure a star who could elevate them from play-in tournament team to legitimate contender. The power dynamic now appears to be shifting.
Mitchell’s playoff performances against the Pacers while his teammates were dealing with injuries and particularly his 89-point explosion across Games 6 and 7 against Orlando in 2024 demonstrated his value as a postseason performer. But is any 6-foot-3 guard approaching his mid-30s worth $80 million annually?
“Does Donovan believe that maybe it might be better off for him to take a smaller contract like Jalen Brunson to allow the Cavs organization to bring in more help?” Sands posed on the podcast.
“I think if Donovan came to them and said, ‘Hey, I’d love to sign a short-term extension,’ the Cavs would do backflips because it would take a lot of awkward tension out of the air,” Watkins responded.
The question might not be whether Mitchell will sacrifice money for winning — it’s whether the Cavaliers will be willing to commit that astronomical sum in the first place.
How this high-stakes financial chess match plays out could define the next era of Cavaliers basketball — and Mitchell’s legacy.
Here’s the podcast for this week:
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