Gambling on college football almost fixed my dysfunctional family Mike Evans, New York Times · July 31, 2020 at 3:36 pm My first mistake was feeling sorry for him. The first season my brother and I bet on college football against each other, I beat him so badly I often bragged I could have lost every single game we gambled on for the rest of the decade and still finished in the money. Each week, we would agree to disagree on five games across the N.C.A.A. schedule. Each win was worth a dollar. Whoever won the most games of the five we selected cashed an additional five bucks. Best out of five, winner takes all for a maximum potential profit of $10 for the weekend.