Most wins by an MLB manager

Connie Mack has the most regular-season wins of any MLB manager, 3,731 over 53 seasons, ahead of Tony La Russa (2,902) and John McGraw (2,677). Joe McCarthy and Casey Stengel won the most titles among them, 7.

MLB managers by regular-season wins, every club summed
#	Manager	Clubs	Seasons	W-L	Pct	Playoffs	Titles
1	Connie Mack	Pittsburgh Pirates, Athletics	53	3,731-3,948	.486	24-19	5
2	Tony La Russa	Chicago White Sox, Athletics, St. Louis Cardinals	35	2,902-2,515	.536	71-61	3
3	John McGraw	New York Yankees, San Francisco Giants	32	2,677-1,886	.587	26-28	3
4	Bobby Cox	Atlanta Braves, Toronto Blue Jays	29	2,504-2,001	.556	67-67	1
5	Bruce Bochy	San Diego Padres, San Francisco Giants, Texas Rangers	28	2,252-2,266	.498	57-37	4
6	Sparky Anderson	Cincinnati Reds, Detroit Tigers	26	2,194-1,834	.545	34-21	3
7	Dusty Baker	San Francisco Giants, Chicago Cubs, Cincinnati Reds, Washington Nationals, Houston Astros	26	2,183-1,862	.540	57-31	1
8	Bucky Harris	Minnesota Twins, Detroit Tigers, Boston Red Sox, Philadelphia Phillies, New York Yankees	29	2,157-2,218	.493	11-10	2
9	Joe McCarthy	Chicago Cubs, New York Yankees, Boston Red Sox	24	2,125-1,333	.615	34-10	7
10	Walter Alston	Los Angeles Dodgers	23	2,040-1,613	.558	23-21	4
11	Terry Francona	Philadelphia Phillies, Boston Red Sox, Cleveland Guardians, Cincinnati Reds	25	2,033-1,751	.537	44-36	2
12	Leo Durocher	Los Angeles Dodgers, San Francisco Giants, Chicago Cubs, Houston Astros	24	2,008-1,709	.540	7-8	1
13	Joe Torre	New York Mets, Atlanta Braves, New York Yankees, Los Angeles Dodgers	23	1,975-1,643	.546	84-58	4
14	Casey Stengel	Los Angeles Dodgers, Atlanta Braves, New York Yankees, New York Mets	25	1,905-1,842	.508	37-26	7
15	Gene Mauch	Philadelphia Phillies, Washington Nationals, Minnesota Twins, Los Angeles Angels	26	1,902-2,037	.483	5-7
16	Bill McKechnie	Pittsburgh Pirates, St. Louis Cardinals, Atlanta Braves, Cincinnati Reds	24	1,842-1,683	.523	8-14	2
17	Lou Piniella	New York Yankees, Cincinnati Reds, Seattle Mariners, Tampa Bay Rays, Chicago Cubs	23	1,835-1,713	.517	23-27	1
18	Jim Leyland	Pittsburgh Pirates, Miami Marlins, Colorado Rockies, Detroit Tigers	22	1,769-1,728	.506	44-40	1
19	Buck Showalter	New York Yankees, Arizona Diamondbacks, Texas Rangers, Baltimore Orioles, New York Mets	22	1,726-1,665	.509	10-15
20	Bob Melvin	Seattle Mariners, Arizona Diamondbacks, Athletics, San Diego Padres, San Francisco Giants	22	1,705-1,624	.512	16-23
21	Mike Scioscia	Los Angeles Angels	19	1,650-1,428	.536	21-27	1
22	Ralph Houk	New York Yankees, Detroit Tigers, Boston Red Sox	20	1,619-1,531	.514	8-8	2
23	Tommy Lasorda	Los Angeles Dodgers	21	1,599-1,439	.526	31-30	2
24	Dick Williams	Boston Red Sox, Athletics, Los Angeles Angels, Washington Nationals, San Diego Padres, Seattle Mariners	21	1,571-1,451	.520	21-23	2
25	Clark Griffith	Chicago White Sox, New York Yankees, Cincinnati Reds, Minnesota Twins	20	1,562-1,367	.533	—
26	Earl Weaver	Baltimore Orioles	17	1,480-1,060	.583	28-18	1
27	Fred Clarke	Pittsburgh Pirates	16	1,422-969	.595	7-8	1
28	Miller Huggins	St. Louis Cardinals, New York Yankees	17	1,413-1,134	.555	18-15	3
29	Wilbert Robinson	New York Yankees, Los Angeles Dodgers	19	1,399-1,398	.500	3-9
30	Joe Maddon	Los Angeles Angels, Tampa Bay Rays, Chicago Cubs	19	1,382-1,216	.532	31-35	1
31	Davey Johnson	New York Mets, Cincinnati Reds, Baltimore Orioles, Los Angeles Dodgers, Washington Nationals	17	1,372-1,071	.562	25-26	1
32	Jimmy Dykes	Chicago White Sox, Athletics, Cincinnati Reds, Detroit Tigers, Cleveland Guardians	20	1,352-1,441	.484	—
33	Chuck Tanner	Chicago White Sox, Athletics, Pittsburgh Pirates, Atlanta Braves	19	1,352-1,381	.495	7-3	1
34	Cap Anson	Chicago Cubs, San Francisco Giants	20	1,292-945	.578	—
35	Charlie Grimm	Chicago Cubs, Atlanta Braves	19	1,287-1,067	.547	8-16
36	Frank Selee	Atlanta Braves, Chicago Cubs	16	1,284-862	.598	5-0
37	Whitey Herzog	Texas Rangers, Los Angeles Angels, Kansas City Royals, St. Louis Cardinals	18	1,281-1,125	.532	26-25	1
38	Clint Hurdle	Colorado Rockies, Pittsburgh Pirates	17	1,269-1,345	.485	10-9
39	Billy Martin	Minnesota Twins, Detroit Tigers, Texas Rangers, New York Yankees, Athletics	16	1,253-1,013	.553	15-19	2
40	Bill Rigney	San Francisco Giants, Los Angeles Angels, Minnesota Twins	18	1,239-1,321	.484	0-3
41	Joe Cronin	Minnesota Twins, Boston Red Sox	15	1,236-1,055	.540	4-8
42	Ron Gardenhire	Minnesota Twins, Detroit Tigers	16	1,200-1,280	.484	6-21
43	Mike Hargrove	Cleveland Guardians, Baltimore Orioles, Seattle Mariners	16	1,188-1,173	.503	27-25
44	Bobby Valentine	Texas Rangers, New York Mets, Boston Red Sox	16	1,186-1,165	.504	13-11
45	Bud Black	San Diego Padres, Colorado Rockies	18	1,186-1,370	.464	1-4
46	Hughie Jennings	Detroit Tigers, San Francisco Giants	16	1,184-995	.543	4-12
47	Lou Boudreau	Cleveland Guardians, Boston Red Sox, Athletics, Chicago Cubs	16	1,162-1,224	.487	4-2	1
48	John McNamara	Athletics, San Diego Padres, Cincinnati Reds, Los Angeles Angels, Boston Red Sox, Cleveland Guardians	19	1,160-1,223	.487	7-10
49	Ned Yost	Milwaukee Brewers, Kansas City Royals	16	1,144-1,238	.480	22-9	1
50	Tom Kelly	Minnesota Twins	16	1,140-1,244	.478	16-8	2

Regular season, every club summed. Clubs carry their names today (the Montreal Expos are the Nationals). From Wikipedia's lists of each club's managers.