Raul is a companion who doesn't really question any decisions you make. This video shows a few different quests that trigger Raul's dialogue related to that.
0:00 - 0:30 | Brotherhood of Steel
0:31 - 1:04 | Mr House
1:05 - 1:19 | Securitron Army
1:20 - 1:38 | Caesar
1:39 - 2:05 | The NCR
2:06 - 3:05 | The Legion (+Extras)
3:06 - 3:29 | Lesser tribes
3:30 - 3:56 | Yes Man
3:57 - 4:08 | Outro