24. New York Knicks
The only thing that hurts more than following a team that never wins, is following a team that used to win and now does not. You can’t miss what you never had, but if you know what success tastes like, then missing out on it year after year is a horrible sensation. The problem for the Knicks is that you have to have been born in the 1960s to remember their two NBA Championship wins a decade later. The hard truth is that only old people remember.
They made the Finals one last time in 1998-99, but since then have been past the first round just once in the past 21 seasons. Not that they’ve even traveled as far as the postseason often. Six times in that period is poor by any team’s standards. It’s confusing how a team with such a massive profile and in such a big city can be so bad. Their losing mentality is down there with the very worst.