Skippers with the most Manager of the Year Awards

For the overwhelming majority of managers, winning a Manager of the Year Award would make their career.

Winning multiple times? Now that’s hard to do. It’s tough enough to get a managerial job in the big leagues – there are only 30 positions, of course. To take home the most coveted award for an MLB manager more than once takes a ton of skill, hard work and, in most cases, longevity.

Since the Manager of the Year Award was established ahead of the 1983 season, just 16 managers have won the award multiple times. Let’s take a look at the legendary managers who have pulled off the rare feat.

T-1) Buck Showalter (4 Manager of the Year Awards)
Years won: AL 1994, 2004, 2014; NL 2022

Time and time again, Showalter has built scuffling teams into postseason contenders, and voters have rewarded him for it. Showalter is the only manager to win the award with four different teams. Despite his regular season accolades, Showalter is the only manager with four MOY awards to not yet win a World Series title.

T-1) Bobby Cox (4)
Years won: AL 1985; NL 1991, 2004-05

Cox led the Atlanta Braves to an MLB-record 14 straight division titles from to 1991 to 2005. That unbelievable streak was bookended by Manager of the Year Awards — one in the first season of the streak and one in the last, in addition to 2004. Cox is best remembered for his two-decade reign at the helm of the Braves, but one of his awards was in 1985 with the Blue Jays, years before he took the Atlanta job.

T-1) Tony La Russa (4)
Years won: AL 1983, 1988, 1992; NL 2002

Only one person has managed more MLB games than La Russa, but no manager has won more MOY awards. La Russa managed in a mind-boggling six different decades, winning the award in three of them. He also won three World Series titles during his long managerial career — one with the Oakland A's and two with the St. Louis Cardinals.

T-4) Terry Francona (3)
Years won: AL 2013, 2016, 2022

All three of Tito's Manager of the Year Awards have come with the perennially overachieving Cleveland Guardians. But long before heading to Cleveland, Francona led the Red Sox to perhaps the biggest accomplishment of all: ending Boston's 86-year championship drought. After winning the award in 2022, he became just the third manager to capture it three times with the same team.

T-4) Bob Melvin (3)
Years won: AL 2012, 2018; NL 2007

Melvin, a northern California native, has managed up and down the West Coast — Seattle, Arizona, Oakland and now, San Diego. Known for being even-keeled and popular with players, Melvin has taken home three Manager of the Year Awards during his time. At just 61 years old, Melvin could find himself moving up this list by the end of his career.

T-4) Joe Maddon (3)
Years won: AL 2008, 2011; NL 2015

Maddon's analytical approach to leading a ball club is common in the big leagues today, so it's easy to forget that he was on the cutting edge for years as far as managers go. Like Francona, Maddon helped one of baseball's "cursed" franchises to its first title in decades. That was the Chicago Cubs in 2016, one year after Maddon won his third Manager of the Year Award.

T-4) Lou Piniella (3)
Years won: AL 1995, 2001; NL 2008

Piniella's colorful personality made him one of the most popular managers in baseball history, but his resume is as good as anyone's, too. He managed in some of the toughest markets (New York with the Yankees and Chicago with the Cubs) and guided some of the best teams ever (the 116-win 2001 Mariners and World Series-winning 1991 Reds), earning three Manager of the Year Awards along the way.

T-4) Jim Leyland (3)
Years won: AL 2006; NL 1990, 1992

Another likeable personality, Leyland did just about everything you can as a manager. He coached a young Barry Bonds with the Pirates, led the Marlins (just five years removed from their inaugural season) to a World Series title, and changed the culture in Detroit, helping the Tigers to two AL pennants. Fourteen years removed from his previous one, Leyland took home his third and final Manager of the Year Award during his first year with the Tigers.

T-4) Dusty Baker (3)
Years won: NL 1993, 1997, 2000

One of the winningest managers in baseball history, Baker finally got his coveted World Series trophy with the 2022 Astros, after 25 years searching for one as a manager. Baker seems to have been all over the place during his managerial career, heading up five different teams. But all three of his Manager of the Year Awards came in orange and black with the San Francisco Giants.

Managers with 2 Manager of the Year Awards

Kevin Cash (AL 2020-21)
Mike Scioscia (AL 2002, 2009)
Jack McKeon (NL 1999, 2003)
Davey Johnson (AL 1997, NL 2012)
Joe Torre (AL 1996, '98)
Sparky Anderson (AL 1984, '87)
Tommy Lasorda (NL 1983, '88)