I wouldn't be surprised if the Basketball Gods doomed Portland against Houston, even up 3-1, because the Basketball Gods hate me and want me to cry. (My late mom was a Beaverton 9-1-1 dispatcher, and she said the switchboard lit up with troublesome behavior after the Blazers got knocked out of the playoffs.)
However . . .
If you're wondering what team has gone almost as long without a playoff series win, here it is. Should Portland defy the Basketball Gods, the reigning champions of fan futility will be Toronto and Milwaukee (2001). The old Charlotte Hornets won in 2002, the Kings/Timberwolves in 2004, and the Sonics (no immediate help imminent there) in 2005.
Portland won the first round but got beaten in the second in 1978 (by Seattle), 1983 and 1985 (by the less-racist-owned Los Angeles team.) Since 1985 they have either lost in the first round (16 times), missed the playoffs (seven times) or advanced at least to the conference finals (three losses, two Finals losses.)
Incidentally, in 1978 and 1983 the NBA playoffs had 12 teams and the first round was best-of-3 (with four byes). In 1985 it was best-of-5 for the first round, having grown to 16 teams in '84. It became best-of-7 in all rounds after 2002, because more playoff games equals more money. Personally I think fewer games in the early rounds was more exciting, just like I'm enjoying this year's playoffs because the favorites aren't getting a free pass. I think the league should go back to a smaller playoff pool and more first-round byes for top teams. However, I am slightly cray-cray.
Let's hope Toronto and Milwaukee are more bummed than us by next Tuesday!