He can sketch a picture and create a tool from the sketch in essentially the same day, whereas his counterparts take just as long just to sketch the tool in a CAD program of some sort.
He has always had a problem with CAD design. He can navigate it, but he has difficulty with actual modeling. Luckily he is at such a rank in his profession to where he has an intern assigned to him to translate his graph paper sketches into document-able CAD files and do other computerized clerical work that he's not up on.
Sure there are some times when knowing how things were done decades ago is useful if you have to repair something, or do something unusual. But what drives machine tools today is throughput, throughput, throughput and the techniques used by today's CNC machining centers completely obsolete entire categories of tools from years past.
What is more likely is that a machinist who was experienced in operating manual machines, and who has modernized his training can command a premium because his skill gained in doing things the manual way give him a better ability to program a controller to do it more efficiently (CAM software is only so good).