The 2026-27 NBA season feels like a make-or-break year for this version of the Cleveland Cavaliers.
Yahoo Sports · September 23, 2026

The first part of the offseason only served to further this gap. While the Philadelphia 76ers , Toronto Raptors , Indiana Pacers , and Boston Celtics all got better, the Cavaliers lost Dean Wade (one of the team's best connectors) and Keon Ellis , and they completely flailed on the LeBron James sweepstakes.
Their championship window seemed to be slamming shut before it was ever really open. That is, until the Cavaliers front office got creative – orchestrating a five-team deal that cost them Dennis Schroder, Max Strus, and future draft capital to net Peyton Watson , the best two-way wing/forward left on the market at that point.
Now, the Cavaliers are officially all the way in. They made the big swing for Watson, shipped out Darius Garland for James Harden ( then extended him ), and gifted Donovan Mitchell a heavy extension. Cleveland has exhausted pretty much all their resources, but is it enough?
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