What does this quote mean speak softly and carry a big stick?

Answer 1

It means he can be a softy but can also get what he wants done. The big stick is a weapon which meant the military power of the US.

Allow me to add to this answer by clarifying Teddy Roosevelt's remark. Roosevelt meant that in negotiations or in speeches regarding foreign policy that it is wise to speak in a diplomatic fashion, not being hard on demands or threats, but at the same time carry the full weight of the US Armed forces ready in case the softly spoken words were ignored.

Answer 2

Theadore Roosevelt - YOU KINKY SON OF A BITCH

He is, of course, referring to the act of carrying his pimp stick when shiz going down.

He prefers to have no interruption when he's on dat ting. Therefore, you must speak softly.

Teddy Rule Number 1 - CARRY THAT BIG STICK. YEH.

Answer 3

That wasn't Franklin Roosevelt. It was Theodore "Teddy" Roosevelt. It meant try to use diplomacy and fair treatment first but if necessary use whatever force was required.