5. Dan Gilbert, Cleveland Cavaliers
We go from the owner whose team blew a 3-1 lead, to the owner whose team overcame that deficit.
Generally speaking, teams with LeBron James on them don’t get the “sentimental favorite” label. But given that no Cleveland team had won a championship since 1964, the Cavs became something of a Cinderella story during the 2015 and 2016 NBA Finals. The problem? People like cheering for Cinderellas, and Gilbert is just so darn hard to cheer for.
Most of the controversy around Gilbert came from two letters he wrote.
One came shortly after James joined the Miami Heat in 2010. Gilbert said a lot in the letter, but most notably he made a championship boast that didn’t quite pan out.
“I PERSONALLY GUARANTEE THAT THE CLEVELAND CAVALIERS WILL WIN AN NBA CHAMPIONSHIP BEFORE THE SELF-TITLED FORMER ‘KING’ WINS ONE,” Gilbert said (H/T ESPN), adding “You can take it to the bank.”
Of course, “The King” won two championships in Miami, but Gilbert left the letter up until LeBron rejoined the Cavs in 2014.
The other letter (via Yahoo Sports) came shortly after Chris Paul was traded to the Los Angeles Lakers, before the deal was vetoed. In the letter, Gilbert complained about the plight of small market teams, “When will we just change the name of 25 of the 30 teams to the Washington Generals?”
Not even three years later, Gilbert’s team signed LeBron James and traded for Kevin Love. Apparently, teams front loading only bothers Gilbert when his team can’t do it.
In 2010, Gilbert wrote a controversial letter, but at least looked principled. In 2017, he looks like a hypocritical blowhard.