I’m still on this manager kick. Bear with me.
Has anyone heard of Jim Clinton or Joe Miller? Yeah, me either. They share the distinction of having lost the most games as a manager without a win. Interestingly, they both did it in 1872 and managed eleven games without taking home a win. Clinton did it with the Brooklyn Eckfords as a player/manager. He did go on to have a ten year career after that.
While Germany-born Miller did technically bat for the Washington Nationals (yeah, haha) in 1872, it was only four times so calling him a player/manager would be a misnomer. Calling him a ballplayer would almost be a stretch since he only played one more year after 1872.
To look at the other side, you won’t find as extravagant streaks on the winning end. You only have to go as far as Mel Harder. Yes, THAT Mel Harder. The All-Star Cleveland Indian pitcher managed three games and won them all. And that’s as the most games a anyone has managed without losing a game.
Harder did this over a period of two years, 1961-62.
I guess this proves that it’s easier to lose than to win.