3. Dave Dombrowski, Montreal Expos, Florida Marlins, Detroit Tigers, Boston Red Sox, Philadelphia Phillies, +19.97
Hired as a 20-something to run the Expos in the 1980s, Dombrowski has been a chief exec for one-sixth of the Major League franchises across his more than 30 seasons in somebody’s front office.
It is both an extensive and impressive record. Over the seasons, Dombrowski has signed 152 draftees who eventually played in the majors, easily the highest body count of all active execs. In 17 seasons, he signed players who eventually combined to amass at least 10.0 WAR. In 13 of those 17 seasons, the WAR count reached 20, in nine it topped 30, and four times it topped 50, peaking at 72.70 in 2004.
The big prize in that 2004 draft class — for the Detroit Tigers — was Justin Verlander, who was drafted first. But Dombrowski’s roster of best picks spans four decades of North Americana: Marquis Grissom and Cliff Floyd for the Expos in the 1980s, Randy Winn, Josh Beckett and Adrian Gonzalez for the Marlins between 1995 and 2000, Verlander in 2004 and then Nick Castellanos, also, for the Tigers, in 2010. Finally Tanner Houck when Dombrowski was president of the Red Sox and Mike Hazen general manager in 2018.
If you want a criticism of Dombrowski, try this one: His draftees haven’t produced a player who enjoyed a 10 WAR career since he drafted Castellanos and Drew Smyly in 2010.