What team now has the longest World Series drought?

[El Supremo]

Not counting the Brewers (Pilots) or the Nationals (Expos) who've never gone.

What team hasn't even been to the World Series in the most years after going there many times?

Hint:

[marked50]

1. The Hindenburgs?

[El Supremo]

2. Oh! The humanity!

The Humanity

[KamaAina]

4. The Reds?

[Auggie]

9. Thread winner

Laughed out loud

[JonLP24]

3. What kind of flag is on the blimp?

Almost looks Canadian except when I zoom in then I can't tell.

Is the answer Pittsburgh?

https://en.m.wikipedia.org/wiki/List_of_Major_League_Baseball_franchise_postseason_droughts

[marked50]

8. Swastikas on the vertical fins

[KamaAina]

5. Also, not counting the Mariners, who've never gone.

The only '70s or later expansion team not to do so, despite setting the record for regular-season wins.

[elephant hunter]

6. Pirates, 1979.

The Brewers were close having been in in 1982 despite what you said. Perhaps the Nationals though having been in the league since 1969 with no appearances but Pittsburgh has the most years since their last appearance.

[ProfessorGAC]

7. Seems Pretty Puny Compared To Cubs

Doesn't it? Yeah, that is 37 years, but compared to 71, seems small.