Funny that no one mentioned Les's second degree connection to Bix -- Les was very good, long-time friend of Bing Crosby. Les accompanied Bing on his best-selling rendition of "It's Been A Long, Long Time." Bing was a huge musical influence on Les, and Bing was the person who gave Les his first open reel tape recorder, and encouraged him to experiment with it.
Les also played with Fred Waring from 1937 - 1941. I'm not knowledgeable about members of the Fred Waring band from that era, but undoubtedly many of them were around the New York scene during the late '20's - early 30's and knew Bix. Maybe someone with more knowledge about Waring's band could fill in the details here.
Anyway, Les was not only a pioneer, but one of the last great Big Band Era musicians who was still playing on a regular basis. We traditional jazz fans may not always appreciate Les's innovations that paved the way for today's hard rock and pop music, but like Bix, Les Paul was driven all his life by a desire to continually try new things and improve himself as a musician.