Hmm… I’m slightly confused where the confusion is…
I’m under the impression that the 14 awg is with reference to these final three windings.
The wire used to make up those final cables doesn’t matter - as long as the cross sectional area is equivalt to 14AWG in the end.
I don’t see how you could think the insides of a motor could be “silicone wire” - silicone wire, which we know hobby wise, is just high strand counts of
0.08mm in dia tinned copper with silicone insulation. This chart may help
In short… he’s making AWG area equivalent wire out of whatever dia enamel coated wire that he uses. Then for the phase leads we terminate/see outside of the motor can he solders on 14AWG silicone wire to that 14AWG enamel wire creation.
Am I right or totally wrong…
Either way the cookie crumbles… I bet Jeff probably regrets working with us sometimes 
Too many skateboard nerds to handle