If that flag pole is metal and you have to 'ground' the antenna for some reason, why not use the pole as the conductor?
No, your discone doesn't need to be grounded for RF purposes. I can't remember seeing a commercially made/sold antenna that needed RF grounding. There's bound to be some around, but I haven't seen them. An end fed wire typically needs it's 'other half' to work so you could consider that an RF ground, I guess.
'Safety grounding' is completely different from 'RF' grounding.
- 'Doc