That's because even if the team loses, he still makes money.
People will still fill up the stadium, buy concession food and team merchandise.
Companies will still buy TV advertising time during the broadcast of his teams game.
He don't fucking care whether the Cowgirls lose or win, or that it's been 28-29 years since the Cowgirls played in the NFC Championship or the Super Bowl.
https://www.si.com/nfl/cowboys/news/...r-bowl-drought
p.s. anyone watched the Hall of Fame preseason game last night? I didn't! Totally Forgot!