Gwynn spent his entire 20-year career with the Padres, winning eight batting titles and five Gold Gloves. But the perennial All-Star had the misfortune of drawing a pair of history's most accomplished teams as opponents in his two World Series appearances. San Diego won the franchise's first-ever pennant in Gwynn's third year with the club but fell to the Tigers in five games. Fourteen years later, Gwynn made it back to the Series -- but the Padres dropped four straight contests to a Yankees team widely considered the best squad ever assembled.
Gwynn consoled himself with pizza.
(Photo: Heinz Kluetmeier/SI, Walter Iooss Jr./SI)