I'm guessing that what you're saying is that there was something indicating that Charles was paying for COBRA insurance on JJ (maybe Lori too?) in the divorce papers.
If that's the case then yes, that indicates two things. One, that Charles had terminated from a prior employer and that his new company didn't have medical insurance. The latter, since I think he was probably self-employed, would make sense. He probably priced medical insurance and determined that continuing coverage for him, JJ, and maybe Lori was going to be cheaper (weighing needed coverage, known Rx expenses, and premims) than purchasing new health insurance until his maximum COBRA period was up. That maximun period varies, depending on the situation from 18-36 months, IIRC.