1) Make sure he's on LinkedIn and have ruthlessly add connections on LinkedIn to people he knows from personal and prior business experience as well as anyone who shares something in common with him (school, church, city, hobbies, anything)
2) Target an industry he's interested in and then companies within that industry
3) Find out intersections between those companies and LinkedIn connections and then contact them
4) Explain to them that he is interested in having his connections make an introduction DIRECTLY to someone in their HR departments
5) Explain to HR his interest and then proactively address his resume gaps with them. I have found in my experience that HR is often attracted to someone who can offer a humble, honest assessment of one's own skills and shortcomings. All he needs to do is indicate that he is passionate about working for that company and often HR will give him a chance in an interview to sell himself further.