Winningest is an adjective invented by loudmouth sports fans used to brag about their
team’s past record. It is used to reflect their team’s past victories to deflect from their team’s current failures.
Nobody says a team is the ‘winningest’ unless their recent statistics are laden with
failure.
The University Of
Michigan is the winningest team in college football! (They haven’t won squat in 2 decades)
We have the winningest team in
history! (Going back to when there were only a handful of teams & blacks weren’t allowed to
play yet)