Anderson led the Tigers to the Majors League best record in 1987, but the team was upset in the ALCS by the Minnesota Twins. He won his second Manager of the Year Award that year. After contending again in 1988 (finishing second to Boston by one game in the AL East), the team collapsed a year later, losing a startling 103 games. During that 1989 season, Anderson took a month-long leave of absence from the team as the stress of losing wore on him. First base coach Dick Tracewski managed the team in the interim.