1. The Cleveland Cavaliers
I almost didn’t include the Cavs on this list because winning a title less than five years ago seems like the type of thing that should make you exempt from the list of miserable franchises. But those title days in Cleveland feel like an eternity ago. And it might be another eternity before those days come back.
With LeBron James now in L.A., the Cavs are forced to build around two point guards drafted in back-to-back lotteries (Collin Sexton and Darius Garland). Can those two play together for the long term? Probably not. They’re both ball-dominant guys who have a long way to go before they can be viable starting guards in this league. I have much more hope for Garland than I do Sexton, though.
Cleveland is also stuck with Kevin Love’s contract. He’s under contract through 2023 and will be making oodles of money as he heads into his mid-thirties. If the Cavs couldn’t trade Love at the 2020 deadline, is there any reason to believe they’ll be able to trade him next year? What about the year after that? They’d probably have to attach a first-round pick, something they’d likely be reluctant to do.
I’m not sure what the future holds for either the Cavs or the Bulls, but I would much rather be a Bulls fan right now.