I could be plain wrong, but the way I see it (unlike many fans), is that he simply played along and didn't ask many questions throughout the years. It was not 'till Jan 2019 events - and then its outcomes (including, specially, the #FreeBritney movement) that Britney started to really fight the cship, that she got Lynne involved, that she cancelled Domination (which we all know wasn't because the Colon thing - IF it is actually real).
I think about that time, or a bit later on, Britney finally took a stand and decided to figure out if he was able to play alongside her, sit down with him, and finally express her wishes. I could be wrong, but I think it's more along these lines than him being frightened or scared of anything that could happen to him. Remember that although we never consider it, the cship brought Britney many advantages - including the fact herself is kind of immune to certain lawsuits and other responsibilities, so I don't think he'd ask her 'Hey Britney good evening! How about dissolving this cship today?', specially because it kind of guarantied his job. The fact he is 'working' now, for me, only shows he's doing his job, which he is paid for, and nothing else.