CLEVELAND, Ohio — At 29 years old, Donovan Mitchell stands at what might be the most critical juncture of his career. The Cavs star has accumulated an impressive résumé: six All-Star appearances, two All-NBA selections (including First Team honors last season), and eight straight playoff appearances. Yet, for all these accolades, Mitchell has never advanced beyond the second round of the playoffs.
In the latest episode of the Wine and Gold Talk podcast, cleveland.com columnist Jimmy Watkins puts Mitchell’s career situation in stark terms: “We’re kind of at a real crossroads here for Donovan. Are you going to become one of these Capital G guys or what? And that’s crucial. ... We’re at a very interesting point in his career.”
The central question emerging around Mitchell isn’t whether he’s great — it’s what kind of great he ultimately is.
Is he the undisputed alpha capable of leading a team to a championship, or is he destined to be an overqualified second option?
Watkins compared the situation to one of years past with a former undersized guard that stole Cleveland’s heart with his individual playoff performances: “Cavs fans have been through this with Kyrie Irving before. We kind of got our answer on Kyrie Irving. Best served as a really, really high end overqualified number two guy.”
The comparison to Carmelo Anthony also emerges multiple times throughout the discussion — a Hall of Fame player with tremendous individual accomplishments but limited playoff success. It’s a comparison that should give Mitchell pause.
What makes this moment particularly pivotal for Mitchell is the timing.
After turning 29 on Sunday, he’s squarely in the prime of his career, but that prime window closes quickly. The next two seasons could define how Mitchell is remembered for generations.
“Once you’re 32, 33, most guys don’t break through as a lead guy by then,” Watkins explains. “If Donovan gets to the point where he’s 33, he’s probably going to be the second-best player on his team. He’s at this point where so much is riding on these next couple seasons.”
Mitchell’s statistical brilliance isn’t in question. In the first-round playoff series against the Orlando Magic in 2024, he scored 89 points over Games 6 and 7 — the second-most in NBA postseason history for those elimination games.
But as Watkins pointedly summarizes: “His legacy right now is a complicated one. And again, it’s not the one you want. It’s basically nice stats, nice accolades, but what did it all lead to?”
The answer to that question — and whether Mitchell can evolve into the championship centerpiece the Cavaliers need — will likely be written over the next two seasons in Cleveland. For Mitchell, it’s all about cementing his legacy as a winner.
Here’s the podcast for this week:
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