San Diego Padres
The Padres have rarely come close to winning the World Series. Since their inception in 1969, the Padres have won two National League pennants. Their first came in 1984.
That year, the Padres went up against the Detroit Tigers. San Diego had Garry Templeton, Graig Nettles, Rich Gossage, Steve Garvey, and a young Tony Gwynn.
San Diego rallied from a 2-0 hole in the NLCS to beat the Chicago Cubs in five games before heading to Detroit for the Fall Classic. Unfortunately, the Tigers were too much for the Padres. Jack Morris won Games 1 and 4 for Detroit, helping the Tigers win the series in five games.
Fourteen years later, they matched up against the dynasty that was the New York Yankees. Gwynn was the only holdover from the '84 team in terms of players. Bruce Bochy was on the '84 roster but was now the manager of the Padres.
San Diego was outmatched by the Bronx Bombers. New York pulled off a four-game sweep against the Friars, with Andy Pettitte earning the clinching victory while Scott Brosius earned series MVP honors. The Padres have yet to reach the World Series since their crushing defeat in '98.