1990 Yankees
Photograph By Vincent Riehl/NY Daily News Archive/Getty Images
Technically, the New York Highlanders of 1908 and 1912 were worse, losing 103 and 102 games, respectively, but few of us were around to see them. In the modern era, the '90 Bombers, at 67-95, were the most terrible team the Bronx has witnessed. Even Don Mattingly was terrible that year, hitting .256 with limited power in 102 games. The upside? Rookie Kevin Maas hit 21 homers in 79 games to kick off his Hall of Fame ... er, never mind.
