You probably haven't heard of Red Klotz. And if I told you Klotz was the losingest coach in the history of basketball (losing 13,000 games), you'd wonder why I'm suggesting him.
If you hadn't guessed, Klotz was the longtime coach of the Washington Generals, an organization that to this day operates independently of their perennial foes, the Harlem Globetrotters. He also owned the team, originally an All-Jewish team named the Philadelphia Sphas, for over six decades, and played on the Sphas and Generals until age 62.
But, despite the ignominity, Klotz still holds several distinctions. He has played in and coached thousands of games, and as such, is also one of the most-watched players and coaches in basketball history (because they always play the most-watched team in the history of basketball, the Gens are the second most-watched team in the history of basketball).
Klotz is the only General to have his jersey retired, and the first non-Globetrotter to receive their legend award. He has also been the player or coach to beat the 'Trotters on the most occasions (either with the Sphas, Gens, or the Gen's eponymous alter ego, the New Jersey Reds), including in 1971 when he personally hit a buzzer-beater as a 51-year-old player-coach.
He also played in the BAA/NBA for one season, winning a championship with the Baltimore Bullets. At only 5'7", Klotz is one of the shortest players with a ring.