Before the judge took the bench, Boston blurted out several comments. He told Action News, "I've served five terms. I have a drug problem."
Boston's mugshots show his evolution throughout the years. His criminal past dates back 27 years.
Legal analyst Mark Broughton said his chatty comments in court combined with his current charges and record isn't a good indication of what may be in his future.
"If the judge looks at the dangerousness of the case and his potential danger to the community, with that type of record, it's more than likely he's going to go back to prison," Broughton said.
But Friday, the felon himself claimed he wants to turn his life around. Sitting in his red jail jumpsuit, he said, "I want a program. I want to change. I'm 44 years old".
In June, deputies had to disable the car Boston was driving after a pursuit through the city and county. Officials used the OnStar feature to end the chase.
But not even that stopped him. Deputies said they were forced to deploy bean bags and a pepper ball to get him to cooperate.
When that didn't work, they sent in a K9 that Boston punched before he was taken into custody.
Broughton says despite his upbeat attitude, he doesn't have a lot to smile about now.
"Even if he has a drug problem, I think the judge is more than likely to say he needs to be taken off the streets," Broughton said.
Boston will return to court in early December, and the judge will hear from deputies about their latest confrontation with him.