Wes Montgomery Guitar Technique: Why Does Playing With the Thumb Sound Different From a Pick?
The same hollowbody guitar sounds noticeably different under the thumb than under a pick, and most of a jazz guitarist's tone lives in the hands. Here's what thumb technique, heavy strings and a clean sound really change.
How Did Wes Montgomery Build a Solo? Single Line, Octaves, Chord Solo — One Arc on Gone with the Wind
Wes Montgomery's solos climb in three layers — single line, octaves, chord solo — and land back in chord melody. Transcribing that whole arc, not one chorus, is what teaches his technique.