James Cole Jr., ’95, Reflects on the Value of Government Service—and the Impact of Law School Connections

It was 2013, and James Cole Jr., ’95, had just spent over a year as the deputy general counsel of the US Department of Transportation. He felt good about his service: the DOT had played a role in the nation’s economic recovery through job creation and stimulus spending on transportation projects, and Cole relished being part of the effort. But by 2013, the economy was rebounding, and it seemed like a good time to rejoin the corporate practice group at Wachtell, Lipton, Rosen & Katz, where he’d worked between 1996 and 2011.

“I figured, well, the president’s been reelected, unemployment is going down—I’m going to go back to New York,” Cole told Law School students during a lunch talk in January.

That’s when a chat with Law School classmate Jesse Ruiz, ’95, changed his mind.

Ruiz, who had served as chairman of the Illinois State Board of Education, vice president of the Chicago Board of Education, interim CEO of the Chicago Public Schools, and on the US Department of Education Equity and Excellence Commission, asked Cole if he knew US Education Secretary Arne Duncan, a former CEO of the Chicago Public Schools.

“I said, ‘I’ve heard of him and he’s a great guy.’ And Jesse said, ‘You ought to go talk to Arne because Arne needs a general counsel,’” Cole told students. “And that is literally how I met Arne Duncan and became his general counsel in the Department of Education.”

For the next two and a half years, Cole played a key role in the Obama administration’s efforts to ensure the civil rights of transgender students, as well as in many others, including enforcement actions aimed at regulating for-profit institutions and work on a program called My Brother’s Keeper, which was created to address persistent opportunity gaps faced by boys and young men of color. In January 2016, Cole was also delegated the duties of deputy secretary of education by then-Acting U.S. Secretary of Education John B. King, Jr.

Cole’s talk was part of the Law School’s Diversity Month programming, which included sessions focused on LGBTQ victims of domestic violence and sexual assault, civil rights and the Jewish and Muslim communities, race discrimination in the sharing economy, deaf/hard of hearing victims on domestic violence and sexual assault, the Black Lives Matter movement, women in the judiciary, and more.

As Cole described his efforts—among other things, the Department of Education was involved in multiple court battles over transgender bathroom rights and the White House’s release of guidelines instructing schools to allow students to use bathrooms corresponding with their gender identity—he emphasized the impact of serving in government, particularly on a high-profile, “lightning rod” issue. There were weighty questions to consider and often many views within the administration, as well as potential conflicts between the federal government and the states that he and others in the administration had to consider.

“I’ve learned so much in my five years in government service about putting aside differences when we can work together,” he said. “I think we’ve done a fairly decent job of that, but it can be tough.”

Cole, who grew up on the South Side of Chicago and was the first in his family to go to college, also talked about the impact the Law School had on his life. He encouraged students to make the most of Law School relationships, experiences, and opportunities, noting that, as a student, he never would have imagined that the “tall, lanky guy whose seminar I wasn’t smart enough to take” would go on to become the president of the United States or that his Constitutional Law professor, Elena Kagan, would become a US Supreme Court justice.

“Please take advantage of being students at what I consider to be the best law school in the United States,” he said. “I remember sitting in your chairs, and I can assure you that but for the University of Chicago Law School I would not have been able to do the things I have done.”