2)The currently moribund Pittsburgh Pirates franchise last won a title in 1979. They won their first World Series in the 1909 season, 99 years ago, so they've won five World Series in 99 years, not a great ratio. Don't expect them to "win her all" this year either, so it's safe to say that the Buccos should be stuck on "5" for a while.Pittsburgh Pirates 5 Titles in 99 seasons 5.05% of the time winning the championship.
In last place in the standings are the Pittsburgh Penguins with 2 titles. While in fairness the Penguins have only been in existence for 40 years, they had little success and never even appeared in the Cup Finals before Mario Lemieux came on the scene. They won back-to-back Cups in '91 and '92, then sunk back into relative obscurity after his retirement until Sidney Crosby and Evgeni Malkin came to town. They came close last year and their young team still has a lot of years to go, so we could look at them closing the current gap on the Pirates during the next several years.