CLEVELAND, OH – JUNE 22: Majority owner of the Cleveland Cavaliers Dan Gilbert waves to the fans during the Cleveland Cavaliers 2016 championship victory parade and rally on June 22, 2016 in Cleveland, Ohio. (Photo by Jason Miller/Getty Images)

In a way, Cleveland Cavaliers owner Dan Gilbert might be the luckiest owner in sports. He bought a team that already featured one of the greatest players ever, in LeBron James and stumbled into the best run in franchise history. Then after LeBron left town, Gilbert did all he could to ensure The King would never be back, writing a petty, embarrassing open letter. James returned to Cleveland despite Gilbert and delivered the owner a championship he had little to do with.

And now Gilbert has managed to screw it up.

On Monday night, the Cavaliers announced they were parting ways with widely respected general manager David Griffin. Reports indicated that Griffin, whose job was to assemble the team’s roster, had a different vision for the team’s roster than did Gilbert, whose job is really just to sign the checks.

It seems Gilbert drove out the only title-winning GM in franchise history because he, an expert in running a (sometimes predatory) mortgage lending company, thought he knew more about basketball than an expert in running a basketball team. Now the Cavs are forced to negotiate a franchise-changing trade without a GM, with Gilbert reportedly eyeing Chauncey Billups—he of zero management experience—to take over for Griffin.

It would be bad enough that Gilbert rode off his GM, but in doing so he also alienated the most important person in the organization. After Griffin’s departure became public, LeBron sent a tweet that was two parts praising Griffin, one part subliminally dissing Gilbert.

Now LeBron appears once again angry at an owner he has never liked. Angry enough to leave Cleveland next offseason? Who knows. But it’s clear that even if LeBron stays, it will again be in spite of an owner he doesn’t like or respect.

Gilbert, as the saying goes, was born on third and thought he hit a triple. Then he got picked off.

About Alex Putterman

Alex is a writer and editor for The Comeback and Awful Announcing. He has written for The Atlantic, VICE Sports, MLB.com, SI.com and more. He is a proud alum of Northwestern University and The Daily Northwestern. You can find him on Twitter @AlexPutterman.

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