Not a good scenario. Since we don't know what he's done five times it's hard to guess the sentence. But, with the criminal history element, it is going to be a longer sentence than before.
https://www.inmateaid.com/ask-the-inmate/this-is-my-dudes-5-time-in-jail-for-the-same-thing-what-39-s-gonna-happen-to-him-it-39-s-alliance-courts-m1ss#answer
Accepted Answer Date Created: February 04,2019