Will decent speakers always out do headphones?

They are totally different experiences and I always prefer speakers but nothing wrong with a really good set of phones.

I've been separated about six months,  right before I left I bought  pair of Grado RS2e and a Rupert Neve headphone amp and it was one of the best purchases ever.   My equipment was in storage since July and I've spent many hours listening to those phones,  and they really sound great...

Some people hate headphones but I don't,  they are quite different than speakers but at night they can't be beat.   I finally have my system set back up but still enjoy the Grados often.  And as far as one being better than the other, I've heard many average systems that don't come close to the Grado / Neve combo.   Headphones as a whole are better than they've ever been.   

I recently upgraded my Grados from the SR80e to a pair of SR325e (aluminum) masterpieces. Man, these cans kill it, so to speak...I don't generally use these in my main rig, although these are so good I bought a second Schiit Magni 3 for that, but generally use the Grados for bedtime reading music with my other Magni. I agree that this question an apples/oranges thing, and my main hifi rig sounds alive in a way that gets most of my "active listening" attention, but great phones...well, they're great!

The Grado SR60 and 80 I have are actually killers, too. But you have to take those stupid foam pads. As they are they’re kind of bland sounding.

It’s an apples/oranges question and is simply answered as speakers use the room, and headphones don’t. No way to compare and answer this question.