The Philadelphia Phillies appeared in the postseason once from 1916 through 1975, which I suppose is an unequaled streak of futility in MLB history. The Phillies’ record in those 60 seasons was 3973-5286, not counting being swept by the Yankees in the 1950 World Series. Their average season record from 1916 through 1975 was 66-88. The Phillies have lost 100 games 13 times, all 13 times coming before the 162-game schedule began in 1962. From 1916 through 1961 they finished 8th out of 8 teams 20 times, then escaped the cellar in the 7 years of a single-division, 10-team National League. When division play began, they finished 5th or 6th in the 6-team N.L. East each year from 1969 through 1973.
I don’t know how people rank the performance of the MLB franchises, but the Phillies, with the exception of two stretches in which they could have assembled dynasties if things had gone a little bit better, have been remarkably bad. In the first would-be dynasty, they went to the playoffs 6 times in 8 years, 1976 through 1983, with an average record of 88-67 in that time, and got to two World Series. In the second, they made it to the playoffs 5 years in a row, but now appear to be in another extended losing stretch.
The Phillies have won 100 games three times: in none of the three seasons did they make it to the Series. On the other side, as noted, they haven’t lost 100 games in a season in the 50+ years since they were first given 8 more games in which to get to 100 losses, which strikes me as one of the more surprising facts about the 30 MLB franchises.