I've never really been a fan of Wilson speakers upon many times hearing them over three decades in various iterations and with various systems and rooms. They never really grabbed my by the soul and immersed me in emotional involvement. That is until I heard their newer model, the Sasha, recently at RMAF. I heard it in three different rooms and in every case it had me from the get go. It was especially great with Dagastinos new amps, but great in all three rooms without exception. I don't know what they've done differently but that Sasha is a winner for me - and that was coming from a prejudice from so many negative experiences listening to previous Wilsons (so I was entirely prepared for the same from these and I was really shocked by what I heard). I have always been impressed with Wilson's scaling of music into a really life-size sound stage with dynamic prowess - but through MAXX and Alexandria in several different systems, as well as previous smaller models, none really seemed to get the heart and soul of the music for me. YMMV, and obviously many others have very different experiences of the same systems I just did not get. I just have to say those Sashas shine brightly for me.
I also got the chance to hear the 009's in two different systems at the recent CANJAM/RMAF, where the Sasha's were making their sirens call from so many rooms. Comparing headphone listening and speaker listening is a apples to oranges, IMHO. Without the visceral impact of music on your largest organ (get your mind out of the gutter man, its your skin) headphones are an entirely different experience from speakers. If you approach headphones with the expectations of them being a substitute for speaker listening I believe you might be disappointed no matter how good the headphone rig. I certainly would, even with the 009's at their best. If you enjoy the headphone experience, the greater sense of intimacy, resolution, and in-your-headspace sound, and or if you require the privacy afforded by cans, then 009's certainly are at the top of that game, and indeed they do sound wonderful and do not have much in the way of competition (LCD-3's at their best certainly qualify in my book). I far and away prefer listening to speakers and given the choice I'll take speakers every single time. Again, YMMV. Just offering yet another point of view.