What MLB manager has managed the most years without a Pennant? September 8, 2022September 26, 2022Baseball, Baseball History The MLB manager that has managed the most years without a Pennant is Gene Mauch. He managed for 25 years. Teams: Philadelphia Phillies (1960-68), Montreal Expos (1969-75), Minnesota Twins (1976-80), California Angels (1981-82, 1985-86)