Winningest

Michael Phelps is the winningest Olympian ever.

She has the winningest smile.

There can be little doubt that Carroll Shelby deserves the high praise he has received from many quarters. On the record he’s America’s winningest big car driver.

[Jody Conradt] is the winningest all-time coach in women's basketball with more than 650 victories.

In just a few short years, Don Shula turned the Dolphins from a laughingstock expansion team into an NFL dynasty. He then went on to become the winningest coach in NFL history.