From 1966-1983 (a 17-year stretch), the Baltimore Orioles didn't just seem to be the sport's best franchise, they were -- appearing in five World Series, winning one during each of the 1960s, 70s and 80s.
Anecdotally and ironically, I can now even confess to a certain level of on-air arrogance regarding the Orioles' position in baseball compared to the lowly Cleveland Indians circa 1985. Night after night during my WFBR radio postgame talk show, whenever I'd give the scores and the Indians were 20 games out of first place by mid-June, I can remember saying, "And the Indians lose to the Royals, 6-2. ... Can you imagine what it must be like to be 20 games out of first by the middle of June? The Indians haven't been to a World Series since they lost to the Giants in 1954, when Willie Mays robbed Vic Wertz. … That's more than 30 years, and with no hope of anything anytime soon."
Well, as we know, the Indians became a pretty damned good baseball team starting in the early 1990s. In fact, they made it to two World Series during a three-season span, losing in six games to the Atlanta Braves in 1995 and seven games to the then-Florida Marlins in 1997, blowing a 2-1 lead in the ninth inning of Game 7 in Miami with the seemingly unhittable Jose Mesa on the mound.