Ares’ $400 Million-Plus Bet on Football Has Turned Ugly

Around three years ago, after deciding it wanted to start placing bigger sports bets, Ares Management Corp. wrote a check for over $400 million to a maverick investor pushing a new model of football ownership.

Ares is now working to claw back more than half of that from 60-year-old John Textor, a former competitive skateboarder and a member of the extended Du Pont family, who spent most of his career as a tech entrepreneur before trying to build a sports empire.

The conflict centers on a loan Ares made to Textor’s Eagle Football Holdings LLC used to finance the ...