My Chicago Law Moment: Charles Senatore, '80, Learned to Look Beyond the Facts

Charles Senatore

My Chicago Law Moment is a series highlighting the Law School ideas, experiences, and approaches that have impacted our students and alumni. Video produced by Will Anderson.

When Charles Senatore, ’80, started his career as a law firm associate, he found himself thinking less about facts and more about how he was going to approach those facts. When he did research, he often looked at more than the language of a holding. He dug into the back story, he looked for a framework, he colored in the big picture. He couldn’t help it; he had been taught at the Law School to ask, “why?”

In this way, he was different from many of his colleagues.

“I’d find myself looking for principles, testing assumptions, looking for analogies … trying to get a feel for the context of the law instead of finding that case or that holding,” said Senatore, an executive vice president at Fidelity Investments and a lecturer at the Law School. “At the end of the day, I feel like I was equipped better to look at the context around a matter.”

Later, when Senatore was working in financial services, he remembers encouraging others to think about that “why?” and to go beyond a regulation’s language.

“What’s the context? Why’s it there? What drove it? What were the issues that caused this to happen?” he said. “You end up getting a sense for the real reasons (driving a particular issue) and how to calibrate the firm’s response.”

Senatore, who remembers being filled with “a sense of awe” as a new law student, said the Law School’s rigorous approach to understanding the framework around an issue, rather than simply sifting through details, shaped the kind of lawyer and thinker he became—though he didn’t fully realize it until later.

“It was sort of lost on me in the middle of the process because I thought, ‘Aren’t I supposed to learn X, Y, or Z?’” he said. “The rigor, some of the headaches, some of the frustration, the self-doubt – it’s a real gift. At the end of the day, you’ll emerge stronger, and you’ll see that in the quality of how you approach things.”