Winningest

An unusual adjective that refers to both the subject and the author simultaneously.

Of the subject: Having the most wins.

Of the author: Being an idiot who can't be bothered to look up a real word.

"Michael Phelps is the winningest athlete in Olympic history"

Winningest

This is not a word, though used by some people. As well as explained to be a word Winningest is not a word.

Announcer: That coach is the winningest coach in hockey currently.
Me: Dude, that's not a word.

Winningest

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)

winningest

To have the most wins.

Our coach is the winningest coach is school history.

winningest

to have either the most wins, or the highest win percentage, depending on the sportscaster

Joe Pa will never be this winningest coach no matter how long he's in the game