Wes Montgomery sounds like he was a nice man, a commodity that can be somewhat hard to find in the music business. He had a wife and lots of kids. He supposedly learned to play guitar when he was already a man. He worked all day in a factory, practiced at night, and strummed the guitar with his thumb instead of a plectrum so he wouldn’t keep his wife and kids up all night. Odd things often make people wonderful. He was well-regarded enough to be touring almost right away, but didn’t like being away from his family, went back home and worked in a factory and played at local places again. Eventually he broke through and became international anyway. I don’t know anyone he’s playing with in the video, but this looks like European TV of some sort. The YouTube comments say they’re Dutch.
He’s a really rare specimen. He obviously always wanted to play in a manner that would be entirely accessible to the general public, but his chops and musicality commanded instant respect, even awe, from even the cool atonal kids. He’s one of those players that never seems to run out of variations on what he knows. He never seems to be repeating himself. Even towards the end of his career, when he did jazzesque versions of profoundly pedestrian pop songs, no one snickered behind his back. Wes Montgomery’s version of Windy might still be a version of Windy, but he never made anything worse. He wasn’t capable of it.
I think he needs to be considered among the most influential jazz musicians ever, because more people paid attention to him, one way or the other, than anyone else.