New York Yankees: Brian Cashman enters historic territory

With his four-year extension announced Tuesday, New York Yankees general manager Brian Cashman breaks the all-time durability record for a chief executive who was not also the owner of his team.

By the time his latest extension concludes at the end of the 2026 season, Cashman will have served 28 seasons as the senior vice president and general manager for the New York Yankees.

New York Yankees: Brian Cashman becoming a part of MLB history

Only three men in the game’s history have worked as one team’s chief executive officer for more than 28 seasons … and all three were also the team owners.

As of 2026, the only three with more historical seniority with one team than Cashman will be Connie Mack, Clark Griffith and Barney Dreyfuss. Mack owned and operated the Philadelphia Athletics between 1901 and 1949 (49 seasons), Griffith owned and operated the Washington Senators between 1913 and 1955 (43 seasons), and Dreyfuss owned and operated the Pittsburgh Pirates between 1900 and 1931 (31 seasons).

When Cashman completes his 28 seasons running  the Yankees, he also will have achieved parity with two other two other of the game’s historical figures, and again both were their own bosses. Charles Ebbets owned and operated the Brooklyn Dodgers from 1898 until his death in 1925, and Frank Navin was owner-executive of the Detroit Tigers from 1908 until his death following the 1935 season.

In terms of chief executives who did not also own the team, Cashman will stand alone in 2026. Billy Beane, who like Cashman was hired (by the Oakland A’s prior to the 1998 season), was on pace to match Cashman until Beane was recently removed as team president and reassigned as a senior advisor.

Considering only chief executives who were not also owners, Cashman will actually set the all-time record for seniority when the 2023 season (his 26th) begins. He concluded 2022 in a five-way tie for that honor with Beane, Branch Rickey, John Schuerholz, and Harry Grabiner.

Rickey served as general manager of the St. Louis Cardinals from 1918 through 1942, while Grabiner, long-time business manager of the Chicago White Sox, functioned as general manager from 1921 through 1945. Schuerholz came to the Braves as GM in 1991 and continued in various executive capacities through 2015.

Through 2026, here’s the list of the 10 longest-serving chief executives with one team who did not simultaneously hold a controlling interest in the team.

GM, Seasons (Total)

1. Brian Cashman, New York Yankees, 1998-2026 (28)

2. Billy Beane, Oakland Athletics, 1998-2022 (25)

2. Harry Grabiner, Chicago White Sox, 1921-1945 (25)

2. Branch Rickey, St. Louis Cardinals, 1918-1942 (25)

2. John Schuerholz, Atlanta  Braves, 1991-2015 (25)

6. Charles Feeney, New York-San Francisco Giants, 1947-1969 (23)

7. Jim Campbell, Detroit Tigers, 1963-1983 (21)

8. Joe L Brown, Pittsburgh Pirates, 1957-1976 (20)

9. John Holland, Chicago Cubs, 1956-1975 (19)

9. Al Campanis, Los Angeles Dodgers 1968-1987 (19)

Even considering those who worked as chief executives for multiple teams, Cashman’s 28 seasons will still rank among the game’s all-time elite. He will become one of only 10 individuals in the game’s history to have put in more than a quarter-century running franchises, and the only one to do so with a single team. Here’s how that list will look as of 2026.

Executive, Seasons, (Team(s)) 

1. Branch Rickey, 42 (St. Louis Browns, St. Louis Cardinals, Brooklyn Dodgers, Pittsburgh Pirates)

2. Dave Dombrowski, 37* (Montreal Expos, Florida Marlins, Detroit tigers, Boston Red Sox, Philadelphia Phillies)

3. John Schuerholz, 34 (Kansas City Royals, Atlanta Braves)

4. Brian Cashman, 28 (New York Yankees)

4. Robert Quinn, 28 (St. Louis Browns, Boston Red Sox, Boston Braves)

4. Buzzy Bavasi, 28 (Brooklyn/Los Angeles Dodgers, San Diego Padres, California Angels)

7. Pat Gillick, 27 (Toronto Blue Jays, Baltimore Orioles, Seattle Mariners, Philadelphia Phillies)

7. John Quinn, 27 (Boston/Milwaukee Braves, Philadelphia Phillies)

7. Harry Dalton, 27 (Baltimore Orioles, California Angels, Milwaukee Brewers)

10. Stanley Robison, 26 (Cleveland Spiders, St. Louis Cardinals)

*This assumes Dombrowski continues as Phillies team president through 2026.