Cal Chapman (portrayed by Michael Chernus) is Piper‘s non-judgmental brother. During season two, Cal and his girlfriend, Neri, lived off of the “fat of the land” in a trailer. As per their quirky lifestyle, they used their grandmother’s funeral as on opportunity to get married while the entire family was present. We learn in season three that Cal was initially attracted to Neri because she told him that she has had sex with another women; however, in season three, she reveals that she never had, much to Cal’s dismay (he says he’s heartbroken over the revelation).

At the start of season three, he and his wife are attempting to start a post-World War II ice cream store where they will invent different kinds of flavors;  however, this business venture is abandoned when his sister approaches him with a different business opportunity: the prison panty business.

While Piper is the brains of the operation, Cal takes care of the marketing and business aspect on the other side of the bars. Once their first batch sells out over night, he begins thinking of ways to increase profit. Neri suggests that they make fake used panties, to which Cal argues is not true to their business integrity. However, the fact that they are still living in their parents’ house motivates them to make money quickly. While Neri’s original concoctions are a failure, Cal eventually develops a miso-based serum that mimics the real thing.

While business seems to be looking up, Cal visits Piper in prison to break the news to her: that someone has broken into the account and stolen all of their money. Following the collapse of the business, he and Neri begin buying used clothing and selling it to Seoul, Korea, as “vintage” clothing, a business which becomes surprising lucrative.

In season 4, Cal reveals to Piper that he and Neri are pregnant with their first child.