Donald Trump's animosity toward the NFL is traced back to his ownership of the USFL's New Jersey Generals and a failed 1980s antitrust lawsuit against the league. Trump later attempted to purchase the Buffalo Bills in 2014 but was unsuccessful, leading to claims by Jacksonville Jaguars owner Shahid Khan that Trump's attacks on the NFL are personal and motivated by jealousy. The segment frames the anthem controversy as part of a long-term retaliatory effort by Trump against the "billionaire boys club" of NFL owners.