Which Negro League manager won the most games?  Who won the most pennants?  Oddly enough, nobody has ever (to my knowledge) tried to answer these questions.  A few years back, using the best sources then available (mostly Clark and Lester’s Negro Leagues Book), I tried to.  Since nobody else has done anything about this in the meantime, I thought I might as well post the list I made back then.

I’m not going to guarantee the absolute accuracy of these figures, nor that I didn’t leave anybody out: I just wanted to get a general idea of who the most successful managers were.  As far as was possible, I counted only league games, with a cutoff date of 1950—so Rube Foster, Sol White, and C.I. Taylor, whose best years were before 1920, get short shrift.   

In order of most wins:
1. Candy Jim Taylor (27 years, 3 pennants, 2 world series wins): 627-492, .560
2. Oscar Charleston (19 yrs, 2 pennants): 414-338, .551
3. Vic Harris (13 yrs, 7 pennants, 1 world series win): 334-212, .612
4. Bullet Rogan (5 yrs, 1 pennant): 262-124, .679
5. Rube Foster (6 yrs, 3 pennants): 254-151, .627
6. Dave Malarcher (6 yrs, 3 pennants, 2 world series wins): 250-118, .679
7. Frank Warfield (8 yrs, 3 pennants, 1 world series win): 236-158, .599
8. José Méndez (4 yrs, 3 pennants, 1 world series win): 215-107, .669
9. Dick Lundy (9 yrs, 3 pennants): 209-167, .556
10. John Henry Lloyd (6 yrs, 1 pennant): 172-159, .520

Win(g)field Welch also won 3 pennants, but the figures I have show only an 88-55 record (several seasons were missing back when I compiled this).

Taylor and Malarcher were the only managers to win two Black World Series.

More complete records might put José Fernandez, who piloted the New York Cubans from 1938-1950, among the leaders.  As it is, he stands at 156-174, with one World Series victory.

As I said, this is far from definitive.  In the future I plan to do more work on Negro League managerial records.