Cleveland Cavaliers’ woes teach us to win while you can

While a backup plan is always smart, the Cleveland Cavaliers’ struggles show that maybe it’s best to go all in while you still can.

Throughout all of the 2017-18 season, every roster move made by the Cleveland Cavaliers was looked at through the lens of one LeBron James and how it would impact his impending free agency the coming summer.

One piece the Cavs seemed unwilling to part with for anything less than a Kawhi Leonard during all of last season’s constant turmoil was the Brooklyn Nets‘ first round pick, citing that with LeBron’s impending free agency and no indication on his decision, it would help Cleveland acquire a talented youngster for the inevitable rebuild it would face should James sign elsewhere.

This logic, as sound as it may be in theory, had its flaws. For one, the organization had the opportunity to acquire All-Star Kemba Walker, who would’ve greatly contributed to their postseason run last year and who, at just 28 years of age, could’ve helped the Cavs whether LeBron stayed or not. After all, by extending the contract of Kevin Love, they are technically still trying to win now, correct?

Secondly, draft picks are always sexy in theory, but even a No. 1 overall pick brings with it no guarantee. Even if a team gets its pick right, much needs to be done in order to get to championship contention and even more to be the last one standing.

The Cavaliers were extremely lucky LeBron happened to grow up near where they play. Never before have we seen as great a player feel such a moral obligation to a city and a franchise. He was elevating Cleveland to places it had never been, reaching the Finals year after year. Shouldn’t you try to keep that going as long as possible, no matter the cost?

Owner Dan Gilbert tried to get cute by planning ahead, but in reality, there really isn’t much of a future when LeBron James leaves your team. Just ask Pat Riley, or look in the mirror and have a quick flashback to the 2010-11 season.

Hypothetically speaking, even the presence of Walker might not have been enough to keep James in town, but that’s something one must find out through trial and error. Generational talents don’t come around very often, and they certainly don’t wind up in Cleveland. If you’re lucky enough to get one like the Cavs — one who by all means wanted to stay — you have to do everything you can to keep him in town, even if it means possibly mortgaging your future.

If after all that, LeBron still decided to bolt, Gilbert could’ve sleep well at night knowing he did all he could.

Take the Houston Rockets for example. General manager Daryl Morey understands that his championship window is as wide as the remainder of Chris Paul‘s career, so to help the Rockets compete for a title, he’s willing to trade four first round picks for Jimmy Butler. Say what you will about the deal, but you have to respect the guy for going all in on the closest he’ll ever be to a championship.

A decade of Collin Sexton isn’t worth more than even just a few extra years of LeBron James. The Cavs had their window, intentionally let it close without a fight, and now, after firing their head coach, watching Kevin Love go down with another injury and alienating the veterans on the roster, they’re realizing just how difficult it is to win in the NBA. Maybe they should’ve tried harder to do so while they still had the chance.