Portland Trailblazers.

-They had arguably (or at least tied with Anthony Bennett) the worst #1 draft pick in NBA history in Larue Martin in the early 70s

-had a legit superstar in Bill Walton – but only 2 healthy years of him

-then selected Sam Bowie before Michael Jordan in the 80s

-then had Arvydas Sabonis (one of the greatest international players ever) come into the team very late after his prime even though they already drafted him years before

-then bombed out with Greg Oden who was selected before Kevin Durant

-then had Brandon Roy succumb to a knee disease

You can’t get much more unlucky than that