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)