I think the five was a bit much because it should include current losses, which means the number is probably more like three remaining.
Just to be clear, I said he wouldn't be lower than a headliner in a free card or co-main event in a PPV. That extends to three, but not to five if he doesn't mix in a win somewhere along the way.
I think he's on the Cowboy plan.
If he loses to... let's say Colby.... it's either a co-main event on PPV or main fight on a free card. (I'd bet a co-main event).
If he loses, he'll be the headliner on a free card in his next fight against someone not nearly as headliner worthy as Colby.
Now, that might be his last fight at that point. Or maybe even Colby. It's not like he fights all the time.
But, if he had one more fight in him on a four loss streak, he'd get one more headline act on a free card (maybe as a lead-in to a PPV) where he fights to stay in the company.