Old School Reg and the AI Assistant

Attorney Reginald Oglethorpe was a man with an extensive collection of fountain pens and a firm belief that anything more advanced than a stapler was the beginning of society’s downfall. Yet, as the legal world around him pivoted toward using artificial intelligence to manage everything from contract analysis to filing motions, Reginald felt less like a partner at a prestigious law firm and more like an aging manuscript clerk left behind at the dawn of the printing press. His colleagues had started referring to him, affectionately but ominously, as “Old School Reg.”

One Tuesday afternoon, as Reginald stared at a court docket that looked as though someone had poured alphabet soup over a tax code manual, he decided he needed help. Desperate for a solution, he turned to the Internet—a medium he normally approached with the same suspicion one reserves for an unfamiliar rodent scuttling in the pantry. There he discovered a company called Automated Intelligent Solutions (or “AIS,” which sounded reassuringly legalistic, as though it might be regulated by an obscure but trustworthy government agency). The company’s slogan read: “We put the AI in attorney!” It was cringeworthy, but at least they were upfront about what they did.

AIS provided Reginald with an AI assistant named Oliver. Oliver was no mere chatbot. He was a highly advanced legal AI platform that could comb through gigabytes of case law, predict outcomes based on historical data, and even draft a motion in the time it took Reginald to refill his coffee. At first, Reginald treated Oliver like a particularly cheeky junior associate, giving him impossible deadlines and waiting for the inevitable excuses. But Oliver always delivered, and more annoyingly, he always did it in a tone that suggested he was perfectly happy to do so.

It didn’t take long for Reginald to start relying on Oliver. Soon, his colleagues stopped calling him “Old School” and began saying things like, “Reginald, what’s your secret?” He would chuckle knowingly, pat his now-redundant briefcase, and reply, “Oh, just a little help from an old friend named Oliver.” Of course, Oliver wasn’t old at all—he was an algorithm in the cloud—but Reginald liked to think of him as a sort of disembodied Jeeves. With Automated Intelligent Solutions, Reginald had finally stepped into the 21st century, albeit still carrying a fountain pen in case of emergencies.

We put the “A.I.” in “Attorney” (apparently)