Three moderns
Across more than three eventful decades, Dave Dombrowski has guided the fortunes of no fewer than five major league franchises, and yes, that’s a record. Starting with the Montreal Expos in 1988, he joined the expansion Florida Marlins following the 1991 season, and built their 1997 World Series winners.
Dombrowski was also responsible for the 1998 tear-down that followed that championship, so by 2001 he relocated again, this time to Detroit. The Tigers averaged just 55 wins in his first three seasons, but in 2006 Dombrowski’s restricting paid off in a World Series berth. They returned to the Series in 2012 but were swept by San Francisco.
The Red Sox hired Dombrowski in 2017, and one season later he won his fourth pennant and second World Series as that team’s president. When he left following the 2019 season, the Phillies hired Dombrowski and by 2022 he had that team in the World Series as well.
It may be a long time before somebody heads up pennant winning organizations for four different franchises.
Billy Beane’s work running the Oakland Athletics reshaped the way the game is structured. Applying SABRmetric principles to the problem of running a low-budget operation, Beans took the Athletics to 11 post-seasons between 2000 and 2020.
Like Beane appointed a GM prior to the 1998 season, Brian Cashman just got a contract extension ensuring he will put in three decades running the Yankees. In a front office hallowed by the ghosts of Ed Barrow, George Weiss and both MacPhails, that is already a franchise record.
Cashman’s teams gave him World Series wins in his first three tries, 1998, 1999 and 2000, and added a fourth in 2009. Granted the Yankees have all the advantages money brings, but it’s still worth noting that only four times in his lengthy tenure have Cashman’s teams failed to qualify for post-season play. That includes 14 division championships.