I never dealt with him. beyond the standard stuff. I always used either Boone or Veronica in general. Usually Boone. Then finished the game killing the wannabee Howard Huges and supporting neither legion, nor NCR.
If you want a postapocalyptic holocaust run right, you gotta do it yourself. California liberals in power? Nope. East coast liberals in power? Nope.
Only Volarian Lionheart, Hero of the People (Trademark applied for) can do this properly ;)
Bethesda allows the option of anti-hero then doesn't test the decision tree well.
On my “good” characters, I always help out the small towns and kill off the NCR/Legion/House as quickly as possible. My character doesn’t need to rely on bureaucracies to get stuff done. I never end up using Boone because I hate the NCR too much (and he steals my kills), but I will befriend the Legion temporarily for the ridiculous amounts of ammo they give you.
On my “bad” characters, only the Vendortron, my followers, and Yes Man remain standing at the end of the game. The Legion get to live awhile, though.