Chris' entire life has been about avoiding reality, he never learned a thing from his own birth to incarceration. Breaking him out of this bubble might as well break him, not even prison could break his delusions, his coping mechanism is that strong!
As long as the Tugboat and 14 BC still stand, waiting for him, Chris will stay in his own delusions. Like with everything on Chris' life, it's complicated, on one hand he is a genuinely terrible person with a colossal sense of entitlement whose life could be described as a long string of terrible decisions leading to equally terrible results, but on the other hand Chris is, mentally speaking, a child who never grew up, which really complicates things!
His moment of realization might simply never arrive, even now there are people that still support him. If he gets a slap on the wrist just like last time, it will only make these delusions stronger. It's complicated, but the odds are against him even if he wins the case lol!