In a recent appearance on ESPN’s NBA Countdown, Adrian Wojnarowski made fresh observations on the state of the Ben Simmons saga in Philadelphia. He mentioned one team in particular as a source of intense intrigue for him personally: the Cleveland Cavaliers.
"“Here’s an interesting team to watch, the Cleveland Cavaliers, who before they went on this really incredible start to the season had been engaged with Philly on Simmons. They’ve got some really intriguing assets either in a straight deal with Philly or perhaps a three- or four-team deal, and we reported earlier J.B. Bickerstaff agreed to a new extension today through ’26-’27.” — ESPN Countdown, h/t Ky Carlin of Sixers Wire"
Cleveland has been mentioned in the Simmons saga from the very beginning, but Woj’s sustained elevation of them as a real candidate is notable. Before the season, Cleveland was largely viewed as a rebuilding team hoping to take the next step. That “next step” has evidently been taken, with the Cavs currently sitting fifth in the Eastern Conference with a 19-13 record.
Right now, the Cavs are outright better than the Sixers — in part due to Simmons’ lingering absence. That said, Cleveland is still firmly a tier or two below Brooklyn, Milwaukee, and the East’s true contenders. It would take more star power to elevate them to that level, and for all of his flaws, Simmons does provide a team with star power.
Simmons would immediately rank as the best player on Cleveland’s roster, even with the recent ascent of Darius Garland and Jarrett Allen. He would also provide them with arguably the best perimeter defender in the NBA — a tantalizing thought when paired next to Evan Mobley, who is already one of the NBA’s most versatile and dynamic big man defenders.
The fit is curious, which would suggest the makings of a three-team trade. Jarrett Allen has been great this season, and the defensive dominance of Allen, Mobley, and Simmons would be enough to sustain a competitive roster. But Allen and Simmons make very little sense together offensively, and it could behoove Cleveland to ship Allen to a third team in search of more assets to furnish Philadelphia’s side of the trade return.
Darius Garland doesn’t make too much sense as the backbone of a Simmons deal precisely because of those fit issues, while Collin Sexton’s season-ending knee injury — and looming contract extension — make him someone Philadelphia is unlikely to express interest in. If the Cavs are to do anything, it would probably start with sending Allen to a third team. There would no doubt be plenty of suitors.
Other players of note on Cleveland’s roster are Ricky Rubio, Isaac Okoro, Kevin Love, and Lauri Markkanen.